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 had a fairly high libido so when we became sexually active, we got active. She was also 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."
Holly is one of my friend's younger sisters. She's about four years younger than me and I've known her for nearly ten years. She's brunette, around 5' 2", possibly 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, 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 myself as well. I'm an average guy; about 5' 8" 140 lbs. Brown hair, green eyes. My dick is only 6", but quite thick.
Anyways, I had known Holly'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 bow tie; bow ties 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.
Holly's apartment seemed packed by the time I got there, but it was probably just that it was a small studio. Holly 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, Patrick, showed up a while later. This took me completely by surprise, until I saw he was escorting a girl I recognized as Holly's best friend. When I saw him, I extricated myself from the group I was pretending to talk to and made my way over to greet him. Holly had the same idea.
"Hey man. I wasn't expecting you here," I said as I got close.
Patrick looked surprised. "Dude, me neither. Let's drink."
Bailey and Holly stayed there talking as Patrick 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; Holly 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 wandered 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 Holly, Patrick, Bailey and I. As Holly closed the door on the last party-goer, 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 Patrick and Bailey had been attached at the hip all night. We set it up and started the game. Patrick made the first cup and Holly 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 Patrick 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. Holly and I only had our underwear on now, including her bra. Patrick 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 Holly 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 Holly. 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 a special smile and...
And that was when Patrick decided to bounce the ball, removing two of our remaining three cups. Holly 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 boxer 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 our 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 slid 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. Patrick cleared his throat to shake us from starring.
We shook our heads and returned to the game. Holly shot first. She made it! That tied the game at one cup each. Bailey, perhaps turned on by Holly's and my display, offered to have Patrick remove her panties. I was too busy looking at Holly to notice how things went on the other side of the table. Holly 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 Holly'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 the curve of her waist.
Patrick 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.
