• story Comforting Pete by WhyNotUs (2/3)

    From a425couple@21:1/5 to All on Thu Feb 20 14:42:31 2025
    [continued from previous message]

    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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    WhyNotUs
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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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    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.


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