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Comforting Pete
Story Info
Consoling friend reluctantly agrees to help in other ways.
13.1k words
4.8358.4k17520
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Author's Note: Trying something a little different here. This is planned
as a single story instead of one with multiple chapters. However if
there is interest, this can evolve into future stories. Feedback and
ratings are always appreciated.

FRIDAY

I'm heading to my best friend Pete's house on a Friday afternoon. I
typically got off from work early on Fridays and he wanted me to come
over. His live in girlfriend Jessica had just broken up with him and
moved out abruptly. She was hot, but we never really got along. He was
depressed and invited me over for some pizza, movies, and to help drink
his sorrows away. We had been friends since high school and he always
seemed to be the luckier one of us two. He was taller than me, made more
money than me, owned his own home, and always did better with the
ladies. I pulled into his driveway and walked up to his door. The door
was ajar and I let myself in.

Closing the door behind me I said, "Hey, Dude, where are you?"

"Over here!" He yelled from his TV Room.

I've been in his house a hundred times. It was always clean and neat.
Not this time. There were pizza boxes all over the floor and the sink
was piled up with dishes. I walked in to the TV Room and saw Pete
sitting on the couch nursing a beer. His hair was all messed up and he
hadn't shaved in days. He was wearing and old t-shirt and shorts. This
was not the Pete I knew. Even though it was just me coming over, he
would at least make himself look presentable. He was taking this one hard.

"Dude, what the fuck?!" I said.

"Don't mess with me today, John, I didn't invite you over to break my
balls," he said,

"This place is a mess and you look awful," I said.

"Thanks," he said sarcastically. "Jess used to keep the house clean."

"I get that, but you look like a hobo," I said.

"Fuck you," he said laughing. "Next time I'll put on a tux when you come
over. Now grab a beer and take a seat," he said.

I walked back to the kitchen and took a beer from the fridge. I opened
it and sat next to him on the couch.

"So you want to talk about it?" I asked.

"Not really," he said.

"She just picked up and left?" I asked.

"Yep, didn't even take all her stuff," he said.

"What did she say?" I asked.

"I thought I said I didn't want to talk about it," he said.

"Come on, at least give me the cliffs notes," I said.

"Fine," he began. "I noticed a few weeks ago that she had been going out
with 'friends' a lot. I didn't mind as we had been seeing each other for
over a year and were living together. I went out with my friends, why
shouldn't she be able to go out with hers. Then she was never in the
mood for sex. She was happy to sit on my face, but she wouldn't blow me
anymore. Anytime I tried to fuck her, she would say she was too tired.
Over the last few weeks she got off with my tongue and I had to go jerk
off in the bathroom after."

"Damn Dude," I said, "And then what happened?"

"A week ago she spent the whole night out, didn't call, didn't text," he
said. "When she finally came home she said she was too drunk to drive
home and spent the night at her friend's house. I was mad, but then she
said something like, 'You didn't want me drive drunk and hurt myself or
someone else did you?' She always had her way of convincing me of
things, and I let it go."

"She was really cheating, right?" I asked.

"Yeah, but I was too smitten to realize," he said. "Three days ago it
happened again. She stayed out all night and when I confronted her she
came clean. She had been fucking some dude for the last two months
behind my back. We had a huge fight and she wasn't even sorry. The guy
was moving out West and she wanted to go with him. I was really pissed
and told her to get out. She said fine and that I could throw out all of
her stuff. She was going to start a new life on the West Coast and leave
her old one behind. She walked out the door and I haven't heard from her
since."

"Sorry Dude, that sucks," I said.

"Yeah, I thought she was the one," he said.

"Wait, you don't think she..." I started to ask and then paused.

"What?" he asked.

"You don't think she came home after fucking the guy and made you eat
her out do you?" I asked.

"What? No! Gross," he said. "Although..."

"You think?" I asked.

"I did notice she was extra wet and tasted a little funny the lately,"
he said.

"Holy shit," I said, "You ate her lover's cum out of her pussy?!"

He took a big swig from his beer.

"I don't think that will wash it out," I said laughing.

He punched me on the arm and said, "Fuck you, this isn't funny."

Continuing to break his balls I said, "How many 'the one' is that now?"

"Dick," he said, jokingly.

"Let me think," I said, "Jessica, Jennifer, Jill?"

"Fuck off," he said, "How about you? I don't see you ever have any action."

"I do ok for myself," I said. I was lying, and he knew it. Trying to
deflect I said, "What is it with you and chicks and the letter J anyway?"

"I guess it's a coincidence," he said, "Or maybe I just like to be with
people whose name start with the letter J, right John?"

"Now who's being the Dick?" I asked.

"It would be easier, wouldn't it?" He asked.

"What?" I asked.

"Giving up pussy and being with your best friend," he said.

"What?" I said, "I think all that sperm you ate has gone to your brain."

"Screw you," he said jokingly, "But seriously, you never get any pussy
anyway. What would be the difference?"

"I get plenty," I said.

"Name three girls you've fucked," he said.

I hesitated. He knew there was only the one back in college. I stuttered
and said "I...."

"Yeah, that's what I thought," he said. "There was only that chick Tara
who was so drunk that you fucked her while she was basically passed out.
If I'm wrong name another one."

"There was..."I paused, not being able to lie and come up with other names.

"That's what I thought," he said, "Just the one, barely."

"Thanks Dick," I said

"I bet you'd look cute as a girl," he said.

"Dude, what are you even talking about," I said, "You're not that drunk
are you?"

"No, but if we were drunk, would it be something you'd think about? It
seems like the only time you get lucky is when the other person is
drunk," he said.

"Listen, Fucko, she wasn't that drunk and she said she loved it. The
next day we decided we were better off as friends. As for this bullshit
you're breaking my balls over, you need to cut it out!" I said.

He started laughing hysterically and said, "Thanks Dude, I just smiled
for the first time in days."

I started to laugh too and he dropped the topic. We continued to drink
beers and ordered a pizza. I helped clean the kitchen and picked up the
garbage while we waited for the food. I knew he wasn't going to do it.
After we ate we watched the latest John Wick movie.

As the movie was ending there was a moment of awkwardness. He put his
hand on my thigh and rubbed it a bit. He said, "Thanks for coming over
and helping clean up. It's nice to have someone around the house again."

I didn't react to where his hand was and said, "Happy to do it Buddy."

We made plans to go out to eat the next night and he walked me to the
door and gave me a bro handshake.

Driving home I had the radio on, but my mind was full of my thoughts.
What was that with him rubbing my leg? What was that nonsense that I'd
look cute as a girl? Would it be easier to settle down with my best
friend instead of constantly chasing after pussy that's not interested
in me? Then I snapped out of it and decided I was thinking crazy. I
blasted the radio and focused on the rest of my drive home.

SATURDAY

The next night we went to dinner as planned. We had a nice meal along
with some drinks and then he invited me back to his house. We do this
all the time, so it wasn't anything out of the ordinary. It was a hot
night and when we got back to the house he suggested we go in the pool.

"Dude, that's a great idea, but I didn't bring a suit," I said.

"Yeah, and I don't think you'll fit into one of mine," he said.

"No problem, we can go in next time," I said.

"You can always go skinny dipping," he said laughing.

"Yeah, I don't think so," I said.

"Let me see if I can find you something," he said.

"Ok, I'm gonna hit the bathroom," I said.

I finished up in the bathroom and when I walked out he was standing in
the hallway. He was wearing swim trunks and had taken his shirt off.
That's not what caught my eye though, it was the red bikini on the
hanger he was holding.

"Found you something that should fit," he said.

"What the fuck is that?" I asked.

"One of the bathing suits Jessica left behind," he said. "It looks just
about your size."

"That's not a bathing suit, it's a bikini," I said, "You don't seriously
want me to wear your ex girlfriend's bikini."

"Why not, you didn't want to skinny dip," he said, "You don't have to
wear the top if you don't want to."

"Gee thanks," I said.

"Come on," he said, "We both want to go in the pool. You get dressed and
I'll grab us some beers. Meet me in the pool."

He extended his arm to hand me the hanger. As a reflex I took it. He
walked away and I didn't say anything. I figured what's the difference,
I was going to be underwater most of the time anyway. I walked into the
guest room and got undressed. As a goof I held up the bikini top to my
chest and looked in the mirror. I laughed to myself before putting it on
the bed. I pulled up the bottoms like they were a regular pair of
underwear. He was right, they did fit, but my dick also started to stir.
Was I getting turned on from wearing a bikini? Maybe it's just because I
was pressed against the same material that's touched Jessica's pussy. I
looked in the mirror and it looked like I was wearing a red speedo. I
never had much body hair and being blonde, whatever hair I had was
light. I had to admit I looked pretty good in the bikini bottoms.

I walked out to the backyard and Pete was already in the pool. He
whistled at me and said, "Whoa, I knew that would fit! You look hot! Why
don't you give me a spin so I can see that ass, darling!"

"Fuck you," I said, and I turned around, like I was going to walk
inside, not realizing I was giving him what he asked for.

"Wow, your ass looks great, just like I thought it would," he said.

I turned back around and said, "Dude, cut it out or I'm going home."

"Just breaking your balls," he said. "Come in, the water's wonderful."

I walked closer and I could tell he was staring at me. "What?" I asked.

"It looks like you have some boobies going there, pal, maybe you want to
go put on your top?" He said, laughing.

"That's it!" I said. "I'm going home!"

I turned around and walked back towards the house. I didn't hear him get
out of the pool, but he slowly walked behind me and slapped my ass. Not
expecting it, I jumped forward and yelped. As I turned around, he picked
me up.

"Dude, what are you doing?" I asked.

"We said we were going to hang out in the pool," he said. He carried me
to the edge and threw me in the pool. He jumped in beside me and said,
"See, it's nice in here."

"Yeah, you're right," I said.

We both swam around a bit and I forgot I was wearing a girl's bathing suit.

"I love a night swim," he said, "Jessica and I used to come in with me
all the time. And she wasn't shy about skinny dipping."

"Have you thought about who can replace her? There's gotta be a Jane,
Janine, or Jodie out there for you," I said laughing.

"If I had to go for another J, it why not John?" he said and winked at me.

"Would you cut that shit out," I said, "Why would you want to go from a
hottie like Jessica to me anyway?"

"I'm just fucking around," he said, "You know you're cute when you're mad."

"Whatever," I said, brushing it off. "Where's those beers you were
talking about?"

He got out quick to grab us each a beer and he threw a couple
basketballs into the pool. We started drinking and shooting hoops. He
had a full size basketball hoop at the edge of the pool. He had the
height setup where the rim was approximately 10' from the bottom of the
pool. It was like we could shoot regulation hoops with half of our
bodies underwater. As I've said before, Pete has me beat in a lot of
areas, but basketball was not one of them. I would beat him almost every
time we played and today was no different. I kept draining shots while
most of his shots went clunk off the rim or the backboard. One of his
shots missed so badly his ball went out of the pool and he had to go
chase it.

He got out of the pool and I kept shooting. He retrieved his ball and
was standing at the edge of the pool watching me shoot.

"What?" I asked.

"Nothing, just watching you," he said. "I like the way your little
titties shake when you shoot and you have that cute little bulge in your
bikini bottoms when you jump up out of the water."

"Dude, seriously, this is getting weird. I understand ball breaking, but
I don't need the commentary about my body. Why are you checking me out
anyway?" I asked.

He got back in the pool and handed me my beer.

"You know I'm just messing with you," he said, "I was surprised you
actually put her bikini bottoms on and I've been so horny since she left."

"Well don't get any ideas, I'm not that kind of girl," I said sarcastically.

"Care to make it interesting?" He asked.

"Always," I said.

"I challenge you to a game of H-O-R-S-E," he said.

"You want to play me in basketball?" I asked.

"Yeah," he said, "You pick your stakes."

"Ok, when I win you cut out the comments about me looking like a girl or
anything relating to that topic, forever."

"Deal, but when I win, you have to go inside and cover your little
boobies with your bikini top and then come back in and give me a hand
job," he said.

"Dude!" I screamed.

"What?" He asked. "I feel like that's a fair deal. You think you're so
much better than me at basketball anyway. Why wouldn't you take the deal?"

"You really want me to jerk you off?" I asked. "Don't you want something
else?"

"I used to fool around with Jessica in here all the time. I can really
use a release. I can close my eyes and pretend you're her," he said.

"I don't know, this is getting really weird," I said.

"I'll sweeten the deal, we'll play J-O-H-N. That's 4 shots instead of 5,
and since you think you can't lose this should be a no brainer," he said.

"Fine," I said, "But you better keep up you're end of the deal when I win."

"Scout's honor," he said. "I'll even let you go first."

I took the first shot and drilled it, nothing but net. He continued his
bad performance and clanked one off the rim.

"That's J," I said.

"See you were worried for nothing," he said. "Your shot."

I smiled, knowing I had him. I drilled my next shot and he missed. He
had J-O and I was halfway home. I missed my next shot which was ok, he
still had to make his and I had to miss to get my first letter. Somehow
that happened and I had J. I took a sip of my beer to refocus, which
probably wasn't the best idea. It happened again and we were tied at J-O.

He winked at me and said, "Getting nervous?"

"No way, you were lucky on those two. You better not miss again, because
once I'm in control, you're toast."

He missed and I drilled my shot. He proceeded to miss and he had J-O-H.
One more and I could be done with his nonsense. I was so arrogant that I
went for a crazy deep shot to put him away and missed. He made his next
one and I missed again. I didn't know what was going on. We both had
J-O-H and it should never have been this close.

"Next one wins," he said, "Let me try that deep shot you just missed."

He stepped back and chucked up a shot. From where I was standing it
looked like it was way off. I smiled as the ball hit the backboard hard.
I had another chance to put him away, so I thought. The ball hit the
fiberglass backboard at just the right angle that it bounced off the
front rim and dropped through the net.

"Get the fuck out of here," I said, "There's no way you hit that!"

He shrugged his shoulders and said, "Your shot."

I knew I had to make my shot. There was no way I was going to give my
best friend a hand job while wearing his ex girlfriend's bikini. I
walked over to the spot and took a deep breath. I put up my shot and
exhaled. It was right on, I knew I had drilled it. I would live to fight
another day. All of a sudden a gust of wind blew and it moved the ball
to the side. The wind blew so hard the ball missed the hoop completely
and landed outside the pool.

"Whoa, did you miss on purpose so you would lose?" He asked, laughing.

"Screw you," I said, "That doesn't count. You saw the wind take it."

"All I know is that you missed and lost the game. Looks like you have a
wardrobe adjustment to make," he said.

"You can't really expect me to do that," I said.

"That was the bet and you lost," he said.

"Come on, double or nothing," I said.

"What would double be? Two hand jobs?" He asked.

"No, you come up with something else," I asked.

"Fine, since you're being a baby about it I'll make it easy for you. A
standard foul shot, straight on, a shot you've made a million times.
Make it and we're even," he said.

"Ok, and what do you get if I miss?" I asked.

"Well I expect you to get me off wearing the full red bikini, and...,"
he said and paused.

"Just come up with something," I said.

"Ok, I've been lonely sleeping in my huge bed, so if you miss, I get my
hand job and you have to put on one of Jessica's babydoll nighties,
panties, and perfume, and sleep next to me tonight."

"Seriously?" I asked, a little stunned.

"Yeah, I was going to pretend you were her while you were jerking me
off, and I can pretend you're her in bed. No funny business, I promise,"
he said.

"Fine, just let me make the shot and we can be done with this nonsense,"
I said.

"Go ahead," he said.

I got in position. He was right, I've made this shot a million times. I
felt the wind kick up again and instead of repeating my mistake I waited
for it to calm down. The wind stopped and I raised my arms getting ready
to shoot. I released the ball and right away I knew it didn't feel
right. The ball hit the left side of the rim and rolled around before
dropping into the water. I can't believe I missed again. Now what, I
thought to myself.

"Double or nothing, one more time," I said.

"No way," he said, "You lost, fair and square, twice!"

"But..." I stammered.

"No buts," he said, in a stern voice.

I was stuck, and felt like I had no choice. I got out of the pool and
wrapped a towel around my waist. I walked into the house and into the
guestroom. The red bikini top was staring at me as I walked in. I was
really going to do this. Is there such a thing as a bad hand job? Maybe
I can make it so bad for him that he finally leaves me alone. I picked
up the bikini top and after a few seconds of fiddling with it I got it
on. He was right about my little man breasts. I could feel them being
held snugly by the bikini. My dick started to stir again and I tried to
clear my head.

I walked back out to the pool and was greeted with a whistle again.

"Damn girl, you fill that out nicely!" He said.

"Enough," I said, "Can we just get this over with already."

"Eager aren't we," he said suggestively.

I got back in the pool and I noticed his swim trunks were on the pool
deck. He was naked in the pool waiting for me. I still can't believe I
had gotten myself into this mess. I decided I would just pretend I was
jerking myself off and not think about it too much. Then he started
talking and that idea was gone.

"I was serious, you really look great in your bikini," he said.

I really wish he would stop calling it MY bikini. "Thanks, I guess," I said.

"Are you ready?" He asked.

"Ready as I'll ever be," I said.

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Comforting Pete
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I looked down and he was hard already. We had been friends for more than
10 years, but we had never seen each other naked. Check off another
thing in his column, he was bigger than me. Not just bigger, he was
huge. How could so many girls leave him when he had this huge cock in
between his legs?

"Are you just gonna stare at it or are you going to get me off?" He asked.

I reached my hand underwater and grabbed his hard dick. I couldn't
believe I was touching another man's cock. Not just another man, my best
friend. I stroked him slowly and he closed his eyes. I tried to copy
what I did when I was jerking off, but who was I kidding, I pumped as
fast as I could.

He started to moan, "Oh Jess, oh Jess."

At least he was pretending I was Jessica. I kept stroking him back and
forth. It felt weird to be doing this underwater, but it felt weird to
be doing it in general. I was starting to get into it and that was a
problem, because I was getting hard. I panicked. I didn't want him to
think I was enjoying this. I didn't want him to keep pushing me into
doing these things for him. If he knew I liked it, he wasn't going to stop.

I felt his dick get even harder and from a lifetime of experience I knew
what was about to happen. At least he was going to blow his load
underwater and it wasn't going to get on me.

He moaned even louder and yelled, "Yes, Yes, Yes!"

I felt him throb and I looked down to see him ejaculating into the
water. I moved back just in case, but the white fluid spread out under
the water.

"That was great," he said, "Thank you."

"Well you didn't give me much choice," I said.

"Then don't lose bets!" He said, laughing.

"I'm kinda tired," I said, "Are you ready to get out?"

"Yeah, why don't you take a shower in the guest room and I'll lay out
your sleeping outfit," he said.

"You really expect me to sleep with you?" I asked.

"That was the deal," he said, "And I meant it when I said sleep. Not
sex...unless you want to."

"Let's start with sleep," I said. "I mean, just sleep, this one time."

"Whatever you say Jessica, I mean John," he said sarcastically.

I walked into the guest bedroom and looked in the mirror at myself in
the red bikini one more time before I took it off. I decided to take a
long shower and prolong whatever Pete had planned for me tonight. I took
at him at his word that we would just be sleeping. I got out of the
shower and dried off. Walking back into the bedroom I noticed the bikini
and the clothes I had worn earlier were gone. I was shocked to see what
was waiting for me on the bed. It was a tiny pink satin babydoll with
black trim. Next to it was a matching thong and a bottle of Gucci perfume.

I pulled the thong up my legs. It was really no different that putting
on a pair of underwear or the bikini bottom until the back strap settled
between by cheeks and pressed up against my asshole. I jumped at the
feeling and tried to calm down my hardening dick. I pulled the babydoll
over my head and it barely covered my ass cheeks. I sprayed myself with
the perfume. Wow did I smell girly! My dick was rock hard now and I
started to hyperventilate. My thoughts turned back to what I was
thinking in the pool. I couldn't let him know that I was enjoying this.
Luckily the nightie covered me enough in front that I was able to put my
dick against my stomach and hold it into place with the waist band of
the thong.

I walked into Pete's room and he was already in bed waiting for me. He
was shirtless and only wearing a pair of boxers.

"Wow Jessica, you look even better in babydoll than you do in your
bikini!" He said.

"What's with the Jessica stuff?" I asked.

"I think we'd both rather pretend you're Jessica," he said.

"Ok," I said, giving in.

"Now why don't you climb in cutie," he said.

I gave him a look and got into bed with him. It was a king size bed, and
my hope was it was big enough that he wouldn't have to touch me. Maybe
the smell of her perfume would be enough to get me through this night
and we could go back to normal tomorrow. We were both tired and he
turned off the lights. I was a side sleeper so I rolled over with my
head facing the wall.

SUNDAY

It turns out my chosen sleep position was a mistake as I woke up to Pete
spooning me. His arm was draped around me and even worse his morning
wood was pressed up against me. I tried to squirm and break free of his
embrace, but that must have sparked something in him. He was snoring
lightly so I knew he was still asleep, but I wished his hips knew that,
because they started to move. His dick was pressing in between my cheeks
with only the tiny material of my thong as a barrier. I squirmed more to
try to get out, but he must have thought it was me thrusting back at
him, because he started to move faster.

I heard him moan, "Oh Jess, Oh Jess," just like he had done in the pool.
I heard him take a big gasp and I knew he was waking up. I felt
something wet against my cheeks and he finally rolled onto his back.

"Oh My God, Dude, you came on my ass!" I screamed.

"Oh shit, sorry," he said, "I was having the most amazing dream about
Jessica."

"Yeah, but she's gone, and your cum is all over me!" I said, freaking out.

"What's the big deal?" He asked.

"The big deal?!" I screamed. "We're best friends and we both like women.
Your semen should not be anywhere near me."

"Ok, calm down, we were just having some fun and you were helping me
out," he said.

"I think my debt has been paid," I said, "Can I take off this ridiculous
outfit and wash up now?"

"Yes," he said, "Ill get your clothes out of the dryer and leave them on
your bed. Sorry if you got upset."

"That's ok," I said.

I got up and walked into the guestroom. I stripped off the babydoll and
thong and hopped in the shower. I washed up and scrubbed my ass so hard
as if that would somehow make it cleaner from his cumshot. I got out of
the bathroom and my clothes were on the bed, washed as he promised. I
put on my button down shirt, pants and shoes.

Pete was waiting for me in the kitchen wearing his bathrobe. He asked me
if I wanted to stay for breakfast, but I was anxious to get out of
there. We gave each other a bro-hug and said we would call each other
later. Walking to my car I reached for my keys. My pants had felt weird
when I put them on, but I really wanted to get home so I just ignored
it. Trying to find my car keys I touched something lacy in my pocket. I
pulled it out and in my hand was a black thong. I shoved it back in my
pocket before any strangers could see. I reached into my other pocket
and felt more lace. I didn't dare pull whatever that was out and got in
the car. Needing to know what was in there I pulled it out to reveal a
bra. Pete had put one of Jessica's bra and panties set in my pants
pockets apparently for me to take home.

I walked into my apartment and I was still exhausted. I stripped down to
my boxers and took a nap. I woke up to the sight of black lace. It
dawned on me that this is the first time I had lingerie in my bed. In my
one and only time, we did it under the covers and she kept her shirt on.
I didn't get to see her bra or her panties. My only sexual experience
lasted two minutes and I didn't even get to see her naked. Then the last
twelve hours popped in my head and I realized I just had double the
amount of sexual experiences with Pete.

My mind was spinning and thoughts started to creep into my mind. Is this
something I want to explore? Could I be a girl for him? I knew I still
liked chicks, but my opportunities were severely lacking. I was staring
at the bra and panties and remembered that in all the craziness, he had
cum twice, but I hadn't cum at all. I had a crazy idea to jerk off while
wearing Jessica's lingerie. I pulled up her thong, the second time I had
worn one today, and it felt kinda nice. It took me a second to figure
out the bra, but I was able to get it into place. I looked in the mirror
and thought that if I had the rack Jessica did, I would have looked hot.

I was startled when I heard my phone ding. It was a text from Pete.

"Hey Bud, just checking in on you," he typed.

"Hey," I replied, "All good."

"Good to hear," he typed, "I left you a surprise in your pockets, in
case you were interested in some more fun."

I started to type: "Yeah, I'm wearing them now." I quickly deleted that,
not wanting to tell him. Instead I lied and texted back, "Ok, I'll check
it out. I just woke up from a nap."

He didn't respond again so I went about my business. I got back in bed
and began to rub my nipple through the bra. My dick sprang into an
instant erection. I pulled it out of the thong and was stroking it while
I continued to rub my hardening nipple. It didn't take long and I
exploded all over my stomach. I cleaned up and threw the bra and panties
into my hamper. My emotions were all over the place. First I was
disgusted with myself for what I had done with Pete and just done to
myself, but I also thought I could get used to it. I spent the rest of
the day at home watching TV and catching up with some things on the
computer. I had to be up for work so I went to sleep early.

MONDAY

I am always a good sleeper but last night I was all over the place,
constantly waking up. I rarely dream, but when I do they're always wild.
Tonight was no different as I had multiple sex dreams. The first one was
me having sex with a girl. I couldn't make out her face, but she was
into it. After getting up to pee I fell back asleep hoping that dream
would continue. The second dream was the opposite. This time I was the
girl and I was being fucked by a faceless guy. I must have been enjoying
it because I woke up to my hips thrusting against my mattress and I had
cum all over my boxers. I hadn't had a wet dream since I was a teenager.
What the hell was going on with me?

I got up and took a shower to clear my mind. I went to work and had a
pretty uneventful time. I hadn't thought about Pete or sex the entire
day. That changed when I got home and there was a shopping bag hanging
on my doorknob. I looked down and saw colors staring back at me. I
quickly brought it inside before any of my neighbors could see. I opened
the bag and saw the Red Bikini and the Pink Babydoll and Thong that I
had worn at Pete's over the weekend.

There was a note that said: "J, since you wore these so well over the
weekend and Jessica isn't coming back for them, I thought you'd like to
keep them. P."

What the hell? I thought to myself. Why was he giving me her clothes? I
now had three sets of them. When he texted me a "Hey" later that night I
ignored him. I did what I usually did on a work night, ate dinner and
watched TV. I kept the outfits in the shopping bag and tried not to
think about them.

TUESDAY

I had a better night's sleep followed by the same boring day of work.
When I got home there was another bag waiting for me. This time it was a
Purple Bra and Panties set with a Garter Belt and Purple Stockings.

The note said: "J, just a few more things for your collection. Hope you
enjoy! P."

My collection? This was getting a little out of control now. I put the
bag next to yesterdays and made myself dinner. I tried not to think
about what was inside them, but I couldn't stop staring at the bags.
After eating I sat on the couch and opened the bags. I pulled out the
Bikini and Babydoll and my mind flashed back to what happened when I was
wearing them. I pulled out the Purple set and was drawn to how silky
smooth the stockings felt.

My dick started to tingle a little bit and I figured nobody would know
if I tried it on and played with myself. I quickly stripped down and put
the lingerie on. The familiar feeling of the thong strap against my
asshole felt great and I was a pro at putting on a bra by now. I pulled
the stockings over my almost hairless legs which gave me a huge boner. I
clipped the garter belt around my waist and attached the straps to
complete the look. I checked myself out in the mirror and I thought I
looked pretty good. I sat back down on the couch and started to jerk
off. I tried to think of those sex dreams and realized that any girl
would be laughing at me if she saw me dressed like this. Instead I
pictured myself as a girl getting fucked. My body started to tingle and
I had a huge orgasm, cumming all over my new lingerie. Feeling a little
ashamed I stripped everything off and threw it in my hamper. I realized
that I would have to figure out how to wash all of this lingerie, but
that was a problem for another day.

WEDNESDAY

I had a good sleep and another normal day of work. On my way home my
mind started to wander and I was excited to see what he had left me when
I got home. To my disappointment there was nothing there. I changed out
of my work clothes and couldn't stop wondering why he hadn't brought me
anything today. I let it go and went on with my evening.

THURSDAY

I woke up on Thursday morning and got ready for work. All day I was
thinking about Pete and if he was going to bring me something tonight.
It was strange that he had given me something on Sunday, Monday, and
Tuesday and then just skipped yesterday. I kept looking at the clock
while I was driving home, hoping there was something at my door. For the
second day in a row there was nothing. I had to admit I was enjoying
Jessica's lingerie, but I didn't want to admit to myself that I wanted
to wear it in front of Pete while we fooled around.

I couldn't stop thinking about things and I broke down and texted him:
"Hey, Dude."

It took a little while for him to reply, and he wrote, "Hey Bud, what's up?"

"Not much," I wrote, "Just checking in."

"Oh, I thought you might have something you wanted to ask me," he wrote.

He knew exactly what I wanted, but I didn't want to give him the
satisfaction. "Like what?" I asked. "I haven't really talked to you in a
couple days and I didn't know if you were going to be in the
neighborhood again."

My phone rang. It was Pete. I answered and before I could say hello he
said, "Sounds like you've been missing your surprises."

I froze and all I could say was "I..."

"You didn't say thank you, so I didn't think you liked them," he said.

Finding the words, I said, "I didn't expect you to be bringing me that
stuff."

"But now that I skipped two days, you're upset," he said.

"No, I mean, I..." I started to say and froze again.

"I knew you'd like everything. Tell me, did you try anything on?" He asked.

I couldn't resist anymore I said, "Just her Black Bra and Panties and
the Purple Lingerie set with the Garters."

"Is that all?" He said, laughing. "And they're not hers anymore, they're
yours."

"Whatever you say," I said.

"Did you play with yourself while wearing them?" He asked.

"Uh...yeah," I said.

"Were you thinking about me?" He asked.

"Ew Dude, No," I said, not wanting to admit I pictured myself as a girl
getting fucked.

"Then I guess I have more work to do," he said quietly.

"What was that?" I asked.

"Nothing," he said, "If you want me to bring you something tomorrow, all
you have to do is ask."

"I don't know Dude," I said, "Isn't this kind of weird?"

"If you're enjoying yourself, how can it be weird? I'm happy to bring
you more things, but when I give someone a gift, I expect to be thanked
for it," he said.

"Ok," I said, "Talk to you later."

I hung up and felt embarrassed. I can't believe I admitted to jerking
off while wearing lingerie he gave me. Did I really want to do some more
things with him? It sure beats doing stuff alone. I haven't even
attempted to pick up my own girl in forever. Maybe it will feel good? I
guess it couldn't hurt to try, he is my best friend. We could always
chalk it up as a joke. I'd definitely have to think more about this.

I walked over to my hamper and took out the worn lingerie. I noticed it
had a perfume smell to it. He must have sprayed it before he brought it
over and in my excitement I hadn't noticed. I washed the dirty items in
the sink and let them dry. I made some room in one of my drawers and put
everything away. I had two Bras, three Thongs, a Babydoll, a Garter
Belt, a pair of Stockings, and a Bikini. I had quite a collection so far
and knew I wanted more.

I picked up my phone and texted him, "Thanks Dude for giving me those
things earlier in the week, if there's anything else you'd think I'd
like, I'd appreciate it."

He just replied, "Ok."

FRIDAY

Friday was another light work day and the boss let everyone home early
as usual. I was anxious to see what, if anything, was waiting for me at
my front door. I sped out of work and rushed home. My face lit up when I
saw a bag hanging from my doorknob. The bag was heavier than usual. I
walked into my bedroom and stripped down naked. My cock hardened in
anticipation and I wasn't disappointed. A flash of pink hit my mattress
as I turned over the bag. He had given me a Hot Pink Bustier, G-String,
Garter Belt and Stockings. Then out came a Short Black Tight Dress.
Lastly there was a yellow bikini. He had really gone all out.

The note said, "J, a little something for you to enjoy tonight and I was
thinking you could join me tomorrow for some swimming and barbecue. P."

I picked up the Bustier and wrapped it around my midsection. I tried to
hook it behind my back but there was no way. Then I remembered I've seen
girls hook it in front and spin it around. It was tight, but it had a
little give to it and I knew I would get used to it. I pulled up the
G-String and laughed when my boner was sticking straight out. The tiny
string settled against my hole and I got a chill from that familiar
feeling. I attached the Garter Belt and Stockings. I pulled the Black
Dress over my head and smoothed it down my body. I was never a tank top
or sleeveless shirt kind of guy, so it was a new feeling to have the
straps of a dress over my exposed shoulders. I looked in the mirror and
other than my lack of tits and huge hardon, I looked great. I decided I
would spend the rest of the night wearing this, but first I needed to
take care of myself. I pulled up my dress and jerked off into my
bathroom sink. After that my dick calmed down and I was able to settle
it into my panties. I brushed my dress back down and now I had a smooth
front.

The rest of the night was uneventful. I had a little trouble moving
around with the bustier on, but I was able to make dinner with no
problem. It was when I sat down on the couch with my Little Black Dress
barely covering my ass and my legs in the Pink Stockings that I knew I
wanted to explore with Pete. I was getting hard again and pulled off my
dress. I was going to masturbate while I was wearing my pink lingerie. I
walked over to my full length mirror and started stroking. I closed my
eyes for and pictured Pete behind me. I imagined his hand was the one
that was giving me a hand job. I was rubbing and tugging really fast and
I came all over my mirror. I opened my eyes and giggled to myself. Was I
really wearing Pete's ex girlfriend's underwear while I just pretended
he jerked me off? My life has certainly taken a turn from a week ago.

I felt sexy and thought I could sleep in this outfit. I got into bed and
it was a bad idea. The bustier was too tight and there was no way I
could sleep like this. I took it off and opened my drawer to put it
away. My Pink Babydoll caught my eye and I figured that was close enough
to match what I already had on. I laughed to myself again, because I had
no idea why I was worried about matching outfits, it's like my brain has
totally changed already.

SATURDAY

I had a good nights sleep and I really loved the feeling of the Garters
tugging on my Stockings every time I moved. I woke up to a text from
Pete that said to come over whenever I wanted to. I got out of bed and
into the shower. I knew he expected me to wear the bikini in the pool,
so I decided to shave my entire body. As I mentioned earlier, I didn't
have much body hair, and he probably wouldn't have noticed either way. I
wanted to do this for me.

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Comforting Pete
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I put on the yellow bikini and then put a regular t-shirt and shorts on
over it. I drove to Pete's house and he was already in the backyard. He
had no shirt on and was wearing his bathing suit. We exchanged a hand
slap and a bro-hug.

"Look at you all smooth," he said.

"I can't believe you noticed, my body hair is barely visible most of the
time," I said.

"Well thank you for doing it for me," he said, "I bet that yellow bikini
will look even better with you all shaved. You did bring it, right?"

"Actually..." I said and paused.

I pulled off my t-shirt and exposed my bikini top.

"Whoa, it's so hot that you wore it while your drove over here," he
said, "The bottoms too?"

I pulled off my shorts and said, "Yep."

"Does this mean you want to be a girl for me?" He asked.

"Not so fast, Dude," I said, "I told myself I would see what happens. I
know we both still like chicks, at least I know I do."

"So what are you saying?" He asked.

"I know I like the clothes and I'm curious about what that could lead
to, but as far as being a girl all the time, I'm just not there yet. I
also don't want to ruin our friendship. I'm assuming you feel the same
way," I said.

"Yes, I don't want to lose my best friend, but I also think there's ways
we can make our friendship more interesting," he said.

"This is really something you want?" I asked.

"Yes, and it sounds like you're willing to try," he said.

"Ok, but promise me if I don't like something or it starts to get weird,
we'll drop it and go back to normal," I said.

"Deal," he said.

"So how do you want to do this?" I asked.

"Why don't we cool off in the pool and talk in there?" He offered.

He ran down and jumped in the pool. I was right behind him and I yelled
"Cannonball" as I jumped in. I had worn Bikini bottoms most of the time
we were in the pool last weekend, but it felt weird to jump in with the
top on. We swam around and shot some hoops while drinking beers. It was
a like we were having a normal best friends day, except I was wearing
his ex's Bikini. I guess it was mine now.

He went to take a swig from his beer and I splashed him right in the
face. He gave me a look like he was mad and I started laughing. I
splashed him again and he started to chase me. I was laughing and
swimming away from him while we continued to splash each other. He
finally caught me and grabbed me around my waist. He picked me up and
threw me across the pool near the steps. I was breathing heavy and took
a seat to rest for a minute.

He swam over and smiled. I smiled back and he kissed me. As a reflex, I
kissed him back. He put his hand under my chin and pressed his tongue
against my lips. I opened up to let him in and we were making out.

He stopped and asked, "Was that ok?"

"I guess so," I said, "I've never been kissed like that."

"But did you like it?" he started to ask and then looked down to see I
was hard in my bikini bottoms. "That's a dead giveaway."

I stuttered, "I must have gotten caught up in the moment."

He put his hands under my ass and lifted me up a bit. He pulled down my
Bikini bottoms and my erection popped out. "Whoa, you have a cute dick,
Bud," he said, "All nice and smooth too."

"Thanks," I said shyly. Every guy just loves to hear his dick looks cute.

"But as you know it's not as big as mine," he said, laughing.

I was starting to get annoyed and then he took my dick in his hand and
stroked it. He gave me a big smile and took me in his mouth. I threw my
head back in pleasure as he gave me my first blowjob. I had nothing to
compare it to, but it seemed like he was doing a great job. He was
bobbing up and down quickly while swirling his tongue all around me.

"Dude, if you keep that up I'm going to cum!" I yelled.

He paused to look up at me in the eyes and kept sucking. I felt my dick
begin to swell and I blew my load into his mouth. He sucked me through
my climax and then he sat down next to me on the steps. He pulled me in
for a tongue kiss and I didn't resist. He had swallowed most of my cum,
but there was still some left in his mouth that he pushed into mine.

He stopped kissing me and asked, "How was that?"

"Fucking awesome," I said, "That was my first blowjob."

"Mine too," he said, "At least giving. Looks like you have some catching
up to do."

"Now?" I asked.

"Actually that made me hungry," he said, chuckling, "Why don't we eat
first and see where things go."

"Ok, Dude," I said.

"I was thinking," he said, "Since were gonna try this, do you mind if I
call you Jessica?"

"I guess that will be ok," I said. "What do you want me to call you?"

"She had the cutest pet name for me, do you remember what it was?" He asked.

"Babe?" I asked.

"Yeah, is that ok with you?" He asked.

"If that's what you want, Babe," I said.

"You got it Jess!" He said, smiling. "I had one more thought."

"Yes?" I asked.

"While I fire up the grill, why don't you go pick out an outfit. I know
you've been enjoying what I've picked out for you, so why don't you
choose something to wear for dinner," he said.

"Sure, we've come this far," I said.

"Just go in our closet. Everything is in there, her lingerie and
dresses, if you're in the mood she has a full makeup table, and I think
it would complete the look if you put on a blonde wig," he said.

"Ok, sounds like fun," I said, trying to get into it.

He kissed me on the lips and I walked back towards the bedroom.

I was scared and excited. He gave me an amazing blowjob and was
expecting one in return. What else did he want from me? Did he want to
fuck me tonight too? Did I want him to? I talked myself into trying
whatever this is, but it's getting real, fast.

I walked into the closet for the first time. It was 90% Jessica's
clothes. I opened every drawer to investigate. She had Bras and Panties
in every color imaginable, and there was a drawer dedicated to Garter
Belts and Stockings. She had many different styles of dresses, there
must have been a hundred of them. I can't believe she left all this
behind. I picked what seemed best for an outside barbecue, a White
Sundress with a Pink design on it. I took out matching White Bra with
Pink Trim and a Thong. I got dressed quickly and put on the wig.

I sat down at her makeup table and I had no idea what to do, so I
YouTubed 'Quick Makeup Tricks.' I always liked girls with long
eyelashes, and I was happy to see she had the fake ones. I got those on
and brushed my face and eyelids. Lastly I picked up a tube of lipstick.
It had a pink shade to it, so I figured that was good. I didn't do too
bad for a rookie and I knew Pete wouldn't complain anyway. He would just
be happy for the companionship. I found a pair of white sandals that fit
and I walked out to the backyard. He had put a t-shirt back on and was
finishing by the grill.

"Oh My God Jessica!" He said. "You look amazing!"

"Thanks Babe," I said, playing along.

He pulled me into a kiss and said, "Great job on the makeup! Are you
sure you haven't done this before?"

"God Bless YouTube!" I said.

"Seriously, though," he said, "You were made for this. You're gonna
enjoy being my new Jessica."

"Easy there Dude!" I said seriously, "I have to admit I like the
clothes, but I'm still undecided on the other stuff."

"Don't worry, Babe," he said playfully, "I'm gonna make you feel so
good, you'll be begging for more!"

"Ok, Babe," I said, getting back into character. "But remember, if I
don't like it, we agreed to stop."

"Of course Jess, but trust me, that won't happen," he said.

We sat down and enjoyed dinner. Once again it was no different from any
of our other meals. We had one of our normal conversations, except I was
wearing a dress, makeup and a wig. He had make steaks, grilled
vegetables, and baked potatoes. We switched from Beer to Wine and we had
a lovely meal. I had almost forgot what I was wearing until he reached
across the table and started to stroke my hand.

"Jess, sweetheart, what do you think about returning the favor from the
pool?" He asked.

"Now?" I asked.

"Why not? You can have some pre-dessert before we have ice cream," he said.

"But I've never done that before," I said.

"Yeah, and I hadn't either when I did you in the pool," he said.

"Ok," I said, reluctantly.

He stood up and lowered his shorts and boxers. I had my first real view
of his dick that wasn't underwater. It looked bigger from this angle. He
sat back down and said, "It's your first time, so don't over think it.
Just do what you think would make me feel good."

I stood up and he turned his chair so he was away from the table. I
dropped to my knees and kissed the tip. He moaned and a drop of precum
came out. Instinctively I licked it off. I opened my mouth and took him
in my mouth. He was encouraging me, but he felt so huge in my mouth that
I stopped and started to pull my head back.

He grabbed the back of my head and said, "Don't worry about taking me
all the way in. You'll learn that eventually. Just suck me as best you
can and use a lot of tongue.

I ignored his 'eventually' comment and got to work on the huge cock in
my mouth. The faster I could get him off, the better. I bobbed my head
and tried to copy what he did to me in the pool. I was moving my tongue
and he moaned the loudest when I put pressure on his head. His dick
started to throb and I knew what was about to happen. He announced he
was about to cum and I pulled my head back again. I wasn't sure if I
wanted him to cum in my mouth and I really wasn't sure about swallowing.
He made up my mind for me and held my head still as he ejaculated. I
swallowed the first shot, but then it kept coming until I swallowed
every drop. I stood up and went back to my chair. I wiped my mouth and
took a swig of wine.

"Jessica that was amazing!" He said. "Are you sure that was your first
time?"

"Yes, Babe," I said.

"How was it for you?" He asked.

"I think I like getting one better than giving one," I said.

"Don't worry, you'll get used to it," he said.

"Oh really?" I said.

"I'm telling you Jess, I'm going to give you so much pleasure that
you're going to want to do that for me as a thank you," he said.

"Well that hasn't happened yet," I said.

"It's coming," he said, "Are you ready now, or would you rather have
some dessert first?"

"I could go for some ice cream," I said, wanting to cleanse my taste buds.

"No problem, Jess," he said, "It's getting a little windy out here. Why
don't we go inside and eat on the couch."

I helped him clear the table and he was right about the breeze. My dress
was blowing all over the place. I couldn't decide if I wanted to hold on
to the plates or make sure I wasn't flashing Pete. It's wild that my
mind went there, it's like putting on a dress sent me into full girl mode.

I sat on the couch while he scooped the ice cream. He brought the two
bowls over and put on a baseball game. We watched the game while we
finished our dessert. I put my empty dish on the coffee table and tried
to concentrate on the game. He finished too and inched closer to me
until our hips were touching. He put his arm around me and we continued
to watch the game. He started to rub the back of my neck for a minute or
two and when he took his arm away I made a whimpering sound. His touch
felt so good I didn't want him to stop. I had a feeling there was more
to come as he moved his focus to my thigh.

I am on my best friend's couch watching a baseball game for the
thousandth time, except I'm in a cute little dress and he's massaging me
to get me ready for sex. We've already traded blowjobs and it was almost
time for the main event. I was a little scared, but I knew deep down
that he would never hurt me. His hand crept up my dress and when he
reached my panties he could feel I was getting hard.

"Feeling good, Jess," He asked, already knowing the answer.

"Yeah, Babe, this is nice," I said, not knowing what else to say.

He reached under my legs and pulled them across his lap. "Lean back, I
want to get you ready."

I didn't understand what 'ready' meant, but I listened to him. I was
sitting with my back against the arm of the sofa with my legs draped
straight across his thighs. "Like this?" I asked.

"Perfect," he said.

He reached under my dress and lowered my panties until they were at my
ankles. He took his right index finger, reached towards my mouth and
placed it against my Pink lipstick covered smile.

"Get it nice and wet. I want you to enjoy this whole experience," he said.

I was confused, but I agreed on wanting to enjoy everything, so I sucked
on his finger. After a few sucks he pulled it out and moved it back
underneath my dress. In the back of my mind I knew what was about to
happen, but I still gave him a look as if to say 'Really?' He
interpreted my look and told me to relax. I felt the wet tip of his
finger press against my asshole and pop inside.

"Ohhhh," I gasped.

"Just relax and keep breathing," he said, "I want to open you up so
you're ready for me."

There was that word 'ready' again. I was breathing heavy as he continued
to press his finger deeper.

"I don't think I can do this," I said, "Your dick is so much bigger than
your index finger. How do you expect me to..."

Before I could finish my sentence he flicked his finger against a spot
and I yelped.

"What was that?" I asked, barely able to speak.

"That's your prostate," he said, "If fingertip did that, imagine how
you'll feel when it's my big cock massaging it."

"Can you do that again?" I asked, pleading.

"Oh no, that's not for fingering, that's for fucking," he said. "Let me
finish and we'll go inside."

"Okay," I said, disappointed.

I laid back and let him prepare my asshole for fucking. Once he thought
I could take it he introduced a second finger, and then finally a third.
I moved my hips along with him and he have me a grin. I appreciated how
much care and attention he was putting in so I would be comfortable.
With a real girl our age, she was pretty much ready to go.

He pulled his fingers out to an audible groan from me. The feeling of
being full was gone and my asshole was open. He moved my legs to the
floor and stood up. Then he reached down to take my hand and help me up.

"Ready to go to the bedroom?" He asked.

"As ready as I'll ever be," I said, reluctantly.

I walked with him hand in hand to his bedroom, knowing that shortly my
anal virginity would be gone. I took him at his word that I would enjoy
it, so I went in with that mindset. He sat me down on the bed and gave
me a kiss on the lips. He went into the bathroom and said he would be
right back.

I was nervous and worried. A little worried that it was going to hurt,
but more worried that I was going to let Pete down. I kept telling
myself it would be ok. Then he walked out of the bathroom buck naked and
holding a tube of lube. I started to hyperventilate.

He walked over to me and took my hands. He helped me to my feet and
said, "You ok Jess?"

"Yeah, just nervous," I said.

"Just stay calm and breathe. I'm telling you you're gonna love it," he said.

"Ok," I said.

He pulled my dress over my head and saw my bra and panties in full view.
"Nice choice, virginal white with some pink to match your lips. If it's
ok with you I'd like you to keep your lingerie on."

"Sure," I said.

"Now why don't you lie on your back and I'll try to help you relax," he
said.

I got in the middle of the bed and put my head on one of his pillows. I
felt like I was lying there forever, but it was only a few seconds.
Suddenly he was on top of me and his tongue was in my mouth. We were
making out and I felt his hard cock brushing against my stomach. At the
same time my erection was threatening to pop out of the top of my thong.

He stopped kissing my mouth and started kissing down my body. He sucked
on my neck then moved down to lick my nipples through my bra. The
feeling of his lips on my smooth body was incredible. He continued
kissing down my body until he reached my panties. He pulled the strap
out of my crack and moved it to the side. He gave my dick a kiss through
my panties and then gave a slow long lick to my asshole. I yelped in
anticipation.

I heard the cap of the lube open and he coated his finger and pressed it
inside of me. I jumped at the cold feeling, but it soon warmed up. I
felt him apply some more to me and then I saw him rubbing it up and down
his cock. In a flash he was on top of me again and his tongue was in my
mouth again.

He moved his hand between us and reached for his dick. He told me to
spread my legs and lift my ass up a little bit. This was it, the moment
of truth. He started kissing me again as his tip pierced my sphincter. I
screamed from the pain of the intrusion, but since we were kissing,
nothing came out. He sensed I was in pain so he just kissed me harder. I
tried to focus on the kiss instead of the huge object that was pushing
into my ass. It actually worked. I moved my hands up to hold his cheeks
and kissed him back. I could feel myself loosening and he pushed in a
little more. We kept kissing and he kept inching until he was balls deep
inside of me.

He stopped kissing me, looked me in the eyes and said, "Good girl Jess,
you took me all! How does it feel?"

I was breathing heavy trying to find the words. All I could get out was,
"You're so big! I feel so full!"

He pulled back a couple of inches and slammed back all the way. He said,
"How about now?"

I screamed and said, "Oh My God, so good!

"That's what I like to hear," he said, "I'm gonna fuck you now, ok?"

Confused I said, "Isn't that what we're doing already?"

"Oh no, we're about to see how many times I can make you cum before I
cum once!" He said.

With that he pulled back to his tip and thrust all the way back inside
of me in one smooth motion. I moaned very loudly and he continued. He
was deep fucking me and I was moving my hips to fuck him back. The in
and out motion felt amazing. He had already passed the amount of time I
had fucked a girl, and I already knew this was way better. He slowed his
pace and had me wrap my legs around his waist. He hit my prostate and I
groaned. Now he was fucking me with short strokes, focusing on my
special spot. My whole body had chills.

"Oh My God! What are you doing to me!" I yelled out.

"Feeling good, huh Jess?" he said.

"Right there, right there," I was moaning.

"Yeah, you like that Jessica, you like my dick in your ass?" He asked,
teasing me.

"Oh My God, I've never felt like this. I'm going to explode!" I said.

"Go for it," he said, "Cum for me, cum with my huge cock in your ass!"

My whole body started to convulse and I reached my arms behind his back
to hold on. My hips involuntarily were thrusting against him and my dick
started twitching. I shot so much into the front of my panties I
couldn't believe it. I laid back until my orgasm subsided and he held
still all the way inside of me.

"That was the most amazing thing ever!" I said.

"See, I told you I would make you feel good." He said.

I leaned down to kiss him and said, "Thank you."

"My pleasure, Jess," he said.

Still balls deep in me he put his arms behind my back. He held me tight
and rolled me over without leaving me. I was on top now but in the
position we were in he was slipping out a bit. I leaned back to take him
all the way in again and found myself sitting straight up on him.

"Perfect," he said.

"What?" I asked.

"I feel like we've mastered missionary, and I need a little break. I
think it's time you try cowgirl and ride me," he said.

"Giddy up!" I said.

I pressed down on his thighs to lift myself up until just his tip was
inside of me. I plunged all the way back down and screamed.

"You ok, Babe?" He asked, sounding concerned.

"Oh yeah, your dick is magical," I said.

I started to ride him. Having never done this before from either side I
tried different methods. I would take him deep a few times and then just
a few inches at a time. I eventually got to a spot that gave me chills
again. I looked down and he was laying on a pillow with his hands behind
his head while I was doing all the work. He would let out a sound every
once in a while, but this was for my pleasure right now. I got into a
rhythm where he was hitting my prostate and I didn't stop.

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page 4

Comforting Pete
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"Oh My God, it's happening again!!!" I yelled.

"Yeah Jess, cum for me again!" He said.

"How is this possible?" I asked. "How can I be cumming again?"

Must be magic!," he said, repeating my earlier comment to me.

I started to shake again and focused on that one spot that was doing the
trick. I yelled out and came into my panties again. As I was climaxing,
I sank back down his dick completely, under no control of my own. I sat
still with my eyes closed, taking it all in. When I finally opened them
he was looking at me smiling.

"I can't believe how hard you came," he said.

"Me either," I said.

"Think you have one more in you?" He asked.

"More?" I questioned

"Yeah, I haven't cum yet," he said.

"How can that be?" I asked, knowing that he hadn't.

"That's the benefit of that wonderful blowjob you gave me by the pool
earlier. I can last a lot longer the second time," he said.

"I'm kinda tired," I said.

"No problem, I feel recharged, I can do all the work," he said.

"Ok," I said.

"Lift yourself off of me and get on your hands and knees," he said.
"Time for your first doggy!"

I pushed down on his thighs and he slowly came out of me. I paused as he
slid against my prostate, enjoying the sensation. He popped out of me
and I was left with a huge feeling of emptiness. Not wasting any time I
got on my hands and knees facing the headboard of the bed. I don't know
why, but I wiggled my ass to entice him.

"Somebody's ready," he said, enthusiastically.

He pulled my cum soaked thong down my legs and threw it on the floor. It
was nice not to have my dick constrained against the waistband. His
hands spread my cheeks.

"Wow, your hole looks so cute! I really busted you wide open," he said.

"What does that mean?" I asked, concerned.

"Nothing to worry about," he said, "It just means it will be easier when
I enter you again." He pressed against my hole and didn't stop until his
waist was pressed against my ass. "See?"

"Ooooh," I moaned. "Yeah!"

He pulled back and thrusted into me hard. I yelped and he did it again.

"So deep!" I screamed.

"Oh yeah," he said, "That's what doggy is good for!"

"This is awesome!" I yelled.

"Glad you're enjoying it," he said, "Hold on tight, I'm getting close
and I'm gonna fuck you hard until I blast your insides with a huge load!"

"Oh My God, Yes," I screamed.

He didn't disappoint and was fucking me the hardest he has all night. I
looked down to see my limp dick swinging back and forth. I had been hard
all night and both times when I came from him fucking me. Between the
earlier blowjob and these two, my dick must be done for the night. I put
that out of my mind and focused on his huge cock sawing in and out of my
ass. He made me feel good and now it was his turn.

I wanted him to get there so I kept fucking back and we got into a
rhythm like we've been doing this for years. Then the goosebumps
started. No way I thought to myself. Could this really be happening
again? I found the right spot and tried to focus on him hitting it.

"Ah!" I screamed, "You're not gonna believe this Babe, I think you're
gonna make me cum again!"

"Oh, I believe it," he said, "You're a natural the way you're working
your ass right now!"

I didn't respond, not wanting to admit to myself I was good at receiving
anal sex. I focused on fucking him back and having my third phenomenal
orgasm in a row. I was panting hard and got shivers up and down my
spine. I looked at my dick to see I still wasn't hard. I saw it jerk and
cum started spraying out in a constant stream. My orgasm caused my
asshole contract and I screamed, being as full as I had been all night

"Oh yeah!" He screamed. "Squeeze my dick! I'm gonna blow!"

"Cum inside me! Fill me up with your babies!" I screamed, having no idea
where those words came from.

He pounded into me balls deep and stopped. He grabbed my hips to get me
to stop moving too. He let out a loud groan and my insides felt a warm
splash. He pulled back just a bit and thrust back in. Seven cum shots
later he was spent. He stayed inside of me until he went limp and
slipped out. He rolled over on his back and I did the same.

He kissed me on the lips and said, "Did I convince you?"

I ignored his question and said, "Holy Shit, Babe, how much did you cum
in me?"

"I cum a ton," he said, "You'll get used to it."

"You keep telling me I'll get used to this, you must be really sure of
yourself," I said.

"Come on, you know we're going to be doing this all the time, right?" He
asked.

"I'm still not sure," I said. I knew my answer, but didn't want to tell
him right away.

"Yeah right," he said, "I can guarantee you've never cum three times in
a row that hard before."

"Can we talk about this in the morning?" I asked. "I'm exhausted."

"Of course sweetheart," he said and kissed me.

I fell asleep quickly, because I really was tired. The sex marathon
really wore me out and it had been a long day.

SUNDAY

I was the first to wake up. It was 7am on Sunday and there was no reason
to be awake so early, let alone get out of bed. Yesterday's events came
flying back into my mind. The blowjobs, the three different sex
positions, my orgasms and Pete finally finishing deep inside my ass. His
semen had leaked out of me and I had the pleasure of sleeping in the wet
spot. My night was full of sex dreams, all of Pete fucking me. I
wondered if he'd ever let me fuck him and thought that would be
something we could talk about in the future.

I had made my decision sometime during my second orgasm. This is what I
want. He can dress me up in sexy lingerie and dresses if he's gonna make
me feel this good. Plus all the times we're not fucking, we'll still be
best buds. He was right, this was the perfect setup.

I looked over at him and watched him sleep. He looked so peaceful. I was
anxious to tell him I made up my mind, but I also wanted to thank him
for last night. I pulled back the sheet and saw his naked body. I slowly
took his dick in my hand and it started to get hard. I leaned over and
took his shaft in my mouth. He was fully hard now and I held still. I
wanted him to stay asleep as long as possible. I moved back ever so
slightly and my second blowjob ever was off to a good start. He started
to breathe heavy and I looked up into his eyes as he woke up. I was
staring at him with his dick in my mouth and he had a big smile on his face.

I took his dick out of my mouth and said, "Yes!"

"Yes, what?" He asked me, still groggy from just waking up.

"Yes, you convinced me!" I said.

I took him back in my mouth and continued his first of many morning
blowjobs.

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