Happy 21st Birthday
Ara 6, 2023 // By:analsex // No Comment
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This is my first submission, the first time anyone but me has read my work. I would like constructive feedback. I hope you enjoy. The events are fictional, but the desires and characters are based in real life.
This story contains male on male action and hint of crossdressing. If that offends you, don’t read it.
It all started before I even had my first girlfriend. Somehow I got the idea stuck in my head that I wanted to be fucked by a woman with a strap-on. I honestly don’t know why I thought it would be fun, but it was (almost) exclusively what I thought about when thinking about sex and as a teenage boy, sex was all I thought about. My first girlfriend was very understanding about my desire to be fucked in the ass.
The day I turned 18, was the first time we really started to explore that aspect of our relationship. Surprisingly, the thing that stuck in my head from that night was while she was teasing me to get me horny, she held our makeshift dildo (it was one of those plastic swords from a dollar store) up to my face and got the most serious look in her eyes. Knowing what she wanted, I put the tip in my mouth and pretended to give it head for a few moments. The look on her face was one of intense satisfaction. I knew that wasn’t going to be the last time I had my mouth on a stick.
I bought a strap-on kit online as soon as my first credit card arrived. Sadly, we only had a few opportunities to use it before I left for college. We lasted a little while together while I was away at school. We video chatted regularly and had as much cybersex as I could manage, made difficult by having to deal with a roommate. She admitted to me that one of her fantasies was to have a threesome with another guy and that she wanted me to help pleasure him. I resisted at first, mainly because I had just gotten off before she mentioned this. She went into further detail about what she wanted me to do and I started to get horny again. The ideas stuck with me.
That was some time ago and while I’ve wanted to explore those thoughts, I never have. Not until tonight, that is.
One of my friends was finally turning 21 so she was having a party to celebrate “her first drink.” I think it would be appropriate to describe her now.
Kaitlyn is one of my best friend’s younger sister. She’s about 4 years younger than me and I’ve known her for nearly 10 years. She’s brunette, around 5′ 2″ probably shorter. She’s skinny, but not like a supermodel, and slightly tomboyish. When she’d gone through puberty, her boobs had gotten a huge head start on the process and were quite large compared to her frame. Though she’s grown into them a bit, she’s still sporting 34Ds, maybe DD. Her beautiful brown eyes hide behind glasses, giving her a look that fits her intelligence.
Basically, Kaitlyn is my idea of a perfect woman. I’ve fallen in love with her over the years but she thinks of me as more of a second brother so it isn’t meant to be.
I suppose I should describe me as well. I’m an average guy; about 5′ 8″ 140lbs. Brown hair, green eyes. My dick is only 6″, but quite thick. As you can tell, I’m not quite the admirer of male anatomy as that of female.
Anyways, I had known Kaitlyn’s birthday was coming up, but I was surprised when she called to invite me to come to the party. An idea sprang into my mind as soon as she asked. It was so arousing I could hardly speak to let her know I’d be there. I managed with only a few stutters and immediately jacked off as soon as we hung up.
This could be my chance, I thought. I could get her to think of me differently.
I wasn’t planning to take advantage of her if she got really drunk; her brother was in the Army and was very protective of her. But maybe I could get a kiss, or at most cuddle with her; just enough to get her to stop thinking of me as a brother. I wanted to be more.
And that brings us to last night. A few hours ago, I cleaned myself up as best I knew how and dressed in a nice suit, complete with a bowtie; bowties are cool. I decided I would try to play it off like I’d just gotten out of work and hadn’t had a chance to change. Not really plausible, but I wanted to look sharp.
Kaitlyn’s apartment seemed packed by the time I got there, but it was probably just that it was a small studio. Kaitlyn greeted me at the door.
“I’m really glad you could make it.”
“I wouldn’t miss this. Happy birthday,” I replied. I gave her a hug then she kissed my cheek, shocking me. She was blushing when we parted. I awkwardly handed her the bottle of liquor I’d brought as her present after that, unsure what was really going on. She recovered her usual demeanor and led me inside. She went back to drinking and I got a beer for myself.
It was a standard 21st birthday party. People showed up and others left. There were lots of people there and I didn’t know anyone, at least for a while. One of my other friends, Andrew, showed up a while later. This took me completely by surprise, until I saw he was escorting a girl I recognized as Kaitlyn’s best friend. When I saw him, I extricated myself from the group I was pretending bayan escort to talk to and made my way over to greet him. Kaitlyn had the same idea.
“Hey man. I wasn’t expecting you here,” I said as I got close.
Andrew looked surprised. “Dude, me neither. Let’s drink.”
Bailey and Kaitlyn stayed there talking as Andrew brought his booze into the kitchen. He cracked open a beer and we touched glasses. “How do you know Bailey?”
“We work together. We’ve been talking for a while, but she suddenly asked me out the other day. This is our second date.”
“Awesome. She’s a nice girl.” He hasn’t had the greatest luck with women in the past.
Everyone drank; Kaitlyn most of all. She was constantly smiling, which to me seemed to light up the room. She has a fantastic smile. Every so often she’d catch my eye and smile a little differently, just for an instant. She made a few attempts to spend time with me throughout the night. First she invited me to play beer pong with her; we lost. Then she pulled me over the group of people dancing to the loud music. She got close, but we didn’t touch too much since I was still confused about what was going on. Her attention wondered and I remembered she was probably quite inebriated at this point.
A few more people left, then a few more. As it reached 4 a.m., the party had dwindled to Kaitlyn, Andrew, Bailey and I. As Kaitlyn closed the door on the last partier, she grinned wide. “Who’s up for strip pong?”
The question took the rest of us by surprise, but after a moment’s thought, we all smiled and agreed. My cock stirred at the thought.
The teams were obvious since Andrew and Bailey had been attached at the hip all night. We set it up and started the game. Andrew made the first cup and Kaitlyn volunteered to lose her socks. She almost tipped over and had to use my shoulder to balance as she removed them. I made one after that and Andrew pulled off his shirt.
The game progressed and more skin started to show. I was having a lot of trouble keeping my cock under control as we neared the end of the game. Kaitlyn and I only had our underwear on now, including her bra. Andrew was left with his boxers and Bailey was holding her hands on her breasts to cover her nipples since she was down to her panties.
I was pretty nervous, unsure where to look for most of the time. I was torn between the desire to stare at Kaitlyn in the revealing lingerie she was wearing and trying to remain a gentleman. I figured that being a gentleman had probably gone out the window when we agreed to strip pong. I turned to look at Kaitlyn. She was gorgeous. I barely contained the urge to reach out and touch her, but not before my hand had traveled through some of the space between us. She turned to look at me and our eyes met. She smiled the special smile and…
And that was when Andrew decided to bounce the ball, removing 2 of our remaining 3 cups. Kaitlyn and I looked away sheepishly and each started to remove another article. She stopped as she reached back to unclip her bra. “Let’s do each other’s,” she said shyly.
“Pardon?” I asked, obviously having heard wrong.
In answer, she grabbed my wrists which were at my waist to pull my briefs off. She pulled them gently away from my underwear and put her own there instead. She stepped a bit closer and inched them down then stopped. She took a big breath and blew it out, cooling my rapidly flushing skin. She pulled the clothing down further, crouching as she went. She ended up with her face directly in front of my cock.
I had long since lost control of my member, which stuck out to greet her. Her face was less than a foot from my naked crotch. I was frozen in place, until she tugged my leg to get me to step out of the briefs. I did and laughed as she stood; my face was burning.
“Now me.” When I didn’t move, she took my wrists again and stepped closer. She stopped less than an inch from my throbbing erection, nearly touching her stomach. She pulled my arms around her back to unclip the bra. I started to move on my own, bending a bit at the waist to reach better without poking her with my cock. Doing this brought out faces close together though. She flushed in a fair imitation of my own face and I fumbled with clasp. I smelled alcohol on her breath as she waited; breathing slowly increasing the longer I worked.
Eventually I got it and slide the straps off her shoulder. Her boobs fell only a little as their weight was freed from the fabric. I let the bra fall to the floor and we locked eyes. Andrew cleared his throat to shake us from our stare.
We shook our heads and returned to the game. Kaitlyn shot first. She made it! That tied the game at 1 cup each. Bailey, perhaps turned on by Kaitlyn’s and my display, offered to have Andrew remove her panties. I was too busy looking at Kaitlyn to notice how things went on the other side of the table. Kaitlyn watched them though, maybe trying not to look at me after what had happened. I stared long enough that they had to remind me that it was still my turn. I raised my arm to shoot and stopped.
I pulled Kaitlyn’s arm to turn her to me. She didn’t resist. I pulled her closer, driven by the need. I raised my free hand to her chin and gently lifted her face up to kiss her. Our lips met. Tentatively at first, but increasing in passion as the sexual tension that had built over the last few minutes (or years, I don’t know which) broke down.
I realized then that I hadn’t shot yet. I threw, not caring, just wanting my other hand to be able to touch her soft, warm skin. Her arms snaked up around my neck and mine dropped to curve of her waist.
Andrew and Bailey started groaning and laughing. I didn’t really care about anything beyond the beautiful creature wrapped in my arms, but we did eventually part and see what had happened.
I had made the cup apparently. Bailey was slipping Andrew’s boxers off in the same way Kaitlyn had taken mine. I casually watched as Andrew joined us in nudity. Here’s where things started to get interesting.
Semi-erect, he was pushing 8 inches already. He appeared to either have much better control of himself then I managed, or his body was just unable to provide enough blood to the member while he was still standing. Bailey looked stunned; she didn’t stand up, just sat there looking at his giant dong with her mouth open. I saw from the corner of my eye that Kaitlyn’s jaw had dropped as well. Then I noticed that mine had as well. I quickly closed mine.
Andrew, disliking the attention, pulled Bailey up from her knees and held her hands off his cock in an attempt to maintain some decency in front of company. We were quiet for some time, until Andrew said, “Who wants to play Truth or Dare?”
The girls nodded. Bailey nodded more slowly than Kaitlyn, and still mostly looking down, grinning stupidly. We walked over to the couch and sat in front of it on the floor. Andrew started by saying “Kaitlyn, truth or dare?”
“I dare you to wear as much clothing as the rest of us.”
She stood and pulled her panties off. She was clean shaven and, from my limited view of it, tight. She sat, folding her legs under herself and keeping her legs together. She looked at me. “Truth or dare?”
“How long have you wanted to kiss me?”
I thought for a moment, trying to remember when I first entertained the idea of a relationship with her. “4 years, give or take.”
“I admire your self-control.”
I turned to Bailey. “Truth or dare?”
“Dare!” she said excitedly.
I thought for a moment, trying to think of a good one. “I dare you to kiss Kaitlyn.” Kissing her was all that was on my mind at the moment. Well, mostly kissing.
Bailey looked disappointed, obviously hoping to get physical with Andrew. She crawled on hands and knees over to Kaitlyn, who blushed. Kaitlyn looked away as Bailey got her puckered lips close. Giggling, she said, “Kiss me, woman!” Kaitlyn just laughed and pulled back. Bailey moved closer to her and pushed her backwards, trying to pin Kaitlyn. She didn’t try very hard to get away and eventually let her friend kiss her. I could see their boobs touching and rubbing together. Then I noticed that Bailey was positioned between Kaitlyn’s legs and was grinding forward like she was trying to fuck her. I got the impression that this wasn’t the first time they had been this close.
They broke off after a minute and Bailey sat next to Andrew again. I noticed that he had enjoyed the show; his dick was much more rigid now and it looked almost 10 inches long now. Bailey looked at him and said “Truth or dare?”
“Dare.” Now I felt bad for doing truth…
“I dare you to shove that monster down my throat,” she said almost without waiting for his answer to the question. He grinned.
“That’s not up to me, that’s up to your throat. You think you can handle it?”
She nodded, grinning greedily. He stood and she got to her knees in front of him. Her hand wrapped around his shaft at the base and lifted it up since it was drooping from its own weight. She put her mouth around the end and took about 4 inches in at once. She sucked on it for a while to get it wet. I felt my cock ache, envious. Not of Andrew for getting head, but of Bailey for getting to play with such a nice piece of meat. The old desire to suck a cock came back full force. I sat still though, watching intently as Bailey took more of the cock into her mouth; she was about half way down it now.
Andrew, knowing this would take some time, looked at me and asked “Truth or dare?”
“Dare.” Had to make up for last round.
“I dare you to wear Kaitlyn’s thong.” I should have expected this. This was payback for the last time we’d played ToD; I dared him to switch underwear with his girlfriend of the time. Knowing what I did now, I wondered how he’d stuffed his cock into the thong he’d had to try on.
I held out my hand towards Kaitlyn for her recently removed thong. She smiled broadly as she handed it to me. I stood and slipped it on. It fit snugly, but it did fit; my waist was only a little bigger than her own. My package, renewed to rock hard status by the sight of Andrew’s dick, stick weirdly out around the small patch of fabric. Kaitlyn grinned happily at the sight of me in her thong. I sat again and asked her the question.
“Have you ever had anal sex?” Another attraction of mine, probably fostered from my desire to get fucked myself, was anal.
“Yes,” she replied. I had mixed feelings about the answer. I was excited that she’d been, at least, willing once to do it but at the same time, disappointed that I didn’t have the chance to be the first to explore her body there. And my chances seemed to be getting better and better that I’d be exploring her soon.
“Did you enjoy it?” I asked.
“Oh no, you get one question.” She winked. Still staring at me, she asked “Truth or dare?”
She shifted on the ground while she thought. Suddenly she smiled. “I dare you to put on my bra too.”
I got up and went to grab the bra she’d left at the table. I fumbled with it for a minute then she walked over and grabbed it from me. She showed me how she puts on bras. Secure the clasp in front of her body and turning it around before slipping her arms into the straps and adjusting. On me it didn’t take too much adjusting. It felt strange, particularly since the cups of the bra were empty. She didn’t mind, in fact she rewarded me with another kiss.
Andrew and Bailey were still having fun by the couch. Bailey periodically made 7 or 8 inches disappear into her mouth but she looked determined to get it all. Andrew was inclined to let her try. I asked Kaitlyn the question.
Yes! I just had to say it and she’d have to suck me. I almost said it, but then closed my mouth. I didn’t want to take advantage; if I did it wouldn’t really be her choice to do it. “I dare you to wear my briefs.”
“Oh, turnabout is fair play, I see.” We returned the couch and she picked up my underwear and slipped it on. She looked odd with the baggy briefs on, but it was oddly attractive. I pulled her into an embrace and kissed her. We stood there, wearing each other’s undergarments, kissing for long moments. She put her hands on my waist, much as a guy would normally hold a woman, and I put my arms around her neck. We started laughing. “You look pretty hot in a thong.”
“Really. You have the hips for it.” I flushed. She put her hands on my shoulders and pressed down on them. I decided to just go with it, I was happy doing anything with her. When I was on my knees before her, face near belly, she moved her hand to my face. She caressed it. She stroked my cheek for a moment then she put her index finger on my lips. She gently wiggled her finger in between my lips, which I parted, unthinking. She straightened the finger and slowly moved it in and out of my mouth. I lost myself in the sensation. It reminded me of the times I’d sucked on the dildo I owned. I closed my eyes and started to get into the motion, moving my head back and forth on her tiny faux-penis.
After a minute, she suddenly pulled the finger from my mouth and leaned over close. She kissed me then whispered in my ear, “I thought so.” I could feel her smile against my ear. “I dare you to join Bailey in sucking off Andrew.” I can’t remember which I felt stronger: shock that she knew my desire, pleasant surprise that she wanted me to it, or embarrassed arousal at the thought of the large cock sliding into my mouth. She moved back to look me in the face.
I was still contemplating my response and was only able to stare dumbly at her. Her deep brown eyes were serious mixed with longing. She smiled The Smile and stroked my cheek again. I nodded slowly, unable to speak the response I had waited for a long time to say. She smiled wider, pleased at my answer. She stood straight and walked over to Andrew and Bailey. I didn’t move.
“Andrew, we’re going to try something new here tonight,” Kaitlyn said. Bailey stopped, looking up mildly confused and hoping not to lose her new favorite toy. Kaitlyn continued, “You’re going to sit down and close your eyes and enjoy the blowjob you’re going to get from us. No peeking. In fact…” She walked over to her closet. He looked at me; a little surprise crossed his face when he saw the bra on me. He looked concerned that I would be mad that Kaitlyn was so obviously hitting on him. I just gave him a weak smile and nodded to let him know it was ok. She returned with a blindfold. “You’re going to wear this until told otherwise.” He grabbed the blindfold and put it on. I knew he’d like that, he told me he enjoyed blindfolded sex. He sat in the chair the Kaitlyn brought over and waited. She whispered in Bailey’s ear and I watched the expression change. Bailey beamed and looked at me.
Before sitting in front of Andrew again, Bailey ran over and kissed me full on the mouth. Then she grabbed my hand and pulled me over to my waiting friend. She sat and pulled me down in front of the glistening cock, still slick with her spit. She grabbed the shaft again and started to suck on it. Kaitlyn sat behind me, pressing herself against my back. She said, “Now Andrew, I’m not very experienced at this, just enjoy it.” She kissed my cheek and wrapped her arms around my stomach, seemingly content to get as close to the show as she could.
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