We all had to go on this team-building trip. I’d just won an election to be my college’s Greek system’s treasurer. The President and VP were there, along with eight or nine other “chairpersons.” The women had the exact same grouping of individuals, so there were eighteen of us spread between three vans. Her name was Jen, and she was a cute but not gorgeous girl, my year, totally different major and lots of fun. In the week of the election my girlfriend and I got into a huge fight, somewhat about the fact that I was predicting I’d win and would have to go away for a 4-day trip without her. It degenerated into a screaming battle, the conclusion of which was that I dumped her. It was a long time coming, but I started the twelve-hour drive we had in the back of the second van, pissed off and grumpy. Jen sat with me. I don’t know why.
We were perhaps five or six hours into the trip. It finally came up. “So why are
you so pissed off?” Jen finally said. The other conversations in the van were growing in volume so her quietly asked question went unheard by everyone except me.
I sighed. I had been dreading this. The last thing I really wanted to do was to have to explain why a two-year relationship had ended to a bunch of girls who would certainly judge me based upon my storytelling ability and actions within. But it was easier to just say it and get it done. “Suzanne and I broke up a few days ago.”
“Oh. Oh! For good, you think?” she asked.
“Yeah, for good. From my perspective anyway,” I added.
“How long were you two together?” Jen asked.
“Two years, just under,” I reported dutifully.
“Wow, and it’s just over, just like that?” she demanded.
“No, of course not. But,” I said holding up my hand, “this week was the final act of a long, drawn-out drama.”
Jen considered my words. “I can understand that. My last breakup was that way.” She looked my way. “So why are you pissed?”
“It…I…um.” I shrugged. “I guess, sort of, that I…shit. I don’t know. I just am,” I finally said.
“Oh, bullshit. You just can’t find the words,” Jen returned fire.
“Yeah, yeah. I’m angry because it ended badly. Because she’s nuts and I’m a jerk.”
“Is that true?”
“Which?” I asked. She simply shrugged. “Both,” I said with a rueful smile. “I’m not brazen enough to sit here and say none of it was my fault. But,” I went on, “I’m not going to sugar-coat it, either.”
“So you’re officially single? That’ll make some of the girls on this trip take notice!” Jen said with a smile.
“Ah,” I said, waving her away. We moved on to other topics from there. Around ten-thirty we finally got to the hotel. I was weary from the long ride but several of us were going to rally and hit the bar for some conversation. By eleven I was perched on a bar stool. Tony, the new education guy, was across from me. We were speaking back and forth with Jen and the president of the Panhellenic Counsel, Melissa. The conversation flowed freely and hopped from topic to topic with speed and ease. It’s hard to keep track of conversations like that, because they are so fluid. They change so quickly.
After a couple of beers I was feeling really foggy. My head was all messed up. It might have been over-tiredness, or maybe I just couldn't’t push through that jet-lag feeling I had. In any event, I made some noises like I was going to my room. Thankfully we were all singles, so I didn't’t have to worry about a drunken roommate bursting into the room at three in the morning and doing something entirely stupid. I went to my room alone, not figuring on dealing with anything else. Maybe a quick jerkoff, I thought, just to calm the mind, and then drop off to sleep. I was sliding my key card out of the lock when Jen appeared around the corner.
“Hey, good, I didn't’t miss you!” she said, coming up to me. She had a smile on her face that I suddenly recognized. It was the one conveying interest of a sexual nature.
“What’s up, Jen?” I asked.
“Invite me inside,” she said quickly. I smiled. Well, things were about to get decidedly interesting. She came in and I closed the door behind us. We walked into the room, and she flopped down on one of the two beds. I sat facing her, on the other.
“So?” I said.
Jen smiled. “So.” The silence hung on for a while. Jen finally cleared her throat. “So, do you remember the conversation that spread over the latter half of today’s trip?”
“Forget? It was only a few hours ago. And no, of course I couldn't’t forget. The subject matter made it impossible to forget!” I said.
“Right.” Jen sat quiet for several moments. I wish I could tell you that I knew what was going on in that woman’s head, but frankly, I was clueless. And tired. I yawned in a bone-cracking fashion. That seemed to wake her. “I want to do something with you,” she said. Her voice was husky. Why was that?
“Okay. What?” I asked.
She blinked and blushed a little. I waited, and waited some more. Just when I thought I was going to have to say something, she finally spoke up. “I want to masturbate with you.”
“Oh,” I said stupidly. More like a retard, to be honest. Who talks like that? But Jen was right about the conversation. It seemed like a two-hour talk that the six of us in my van talked about, masturbating and masturbation for hours. Two hours. The who, what, why, when and wheres were all covered in great detail. Somehow the discussions of masturbation turned at one point to discussions about the locations of sexual escapades. There was the back of the car, the garage, the dugout of the baseball field and the school store. It kept coming back around though, back to masturbation. “How, with me?” I finally asked.
“I want to watch you first, and then you can watch me,” she suggested.
“Lights will have to be on,” I said. “You okay with that?”
She shrugged. “I’ll have to be. Hurry up before I lose my nerve,” she added.
I stood and disrobed. I’m not overly proud of my body, but its not awful, either. And Jen was petite and a natural blond. How about that, I marveled. I sat down on the bed, facing her, legs spread. My penis was semi-erect but still pointing down towards the floor. Jen had small breasts topped by small nipples. Her tummy was flat and she was not shaven. The lips of her sex were visible through the matted, curly hair. Her legs were long and smooth. She looked good naked, I thought. I wondered what she thought of me.
“Show me,” she said again. I took my right hand and wrapped the thumb and forefinger in a circle around the base. I slid it upwards until it reached nearly the top of the head and then I brought it back down. I quickly got erect from the sensation of pleasuring myself and staring openly at Jen’s body. It wasn’t great but it was a naked female body. That is generally enough! I got myself nice and erect, and began to play with the base.
“Why are you doing that?” Jen asked me as she watched me twirl my dick around so that the head moved in a large circle.
“I don’t know,” I said truthfully. “Seems like a good idea.”
“Does it feel good?” she asked next.
I shrugged. “Yeah, sort of. Kind of different.”
“You’re big,” she observed.
“Thanks,” I said giving in willfully and immediately to the ego boost. But she wasn’t moving. “Aren’t you, uh, going to, um, get going?”
“I’m not ready yet,” she said. “I’m getting aroused just watching you stroke it. Do you do anything special when you do it?”
“Nah, not really,” I said. “Just…well, stroke and cum I guess.”
“What do you do with your cum?” she pressed.
“Wipe it up. Usually underwear I guess is my cum-catcher.”
“Oh. Wait, do you have one now?”
“Sit tight.” She got up and walked past me. I shook my head – besides this being totally fucking surreal it could happen. Right? She returned with a dry wash cloth. “Use that,” she said. She took her seat again across from me.
“What should I do now?” I asked.
“Do it slowly,” Jen replied in a sultry tone. “Just stroke it, but do it slowly.”
I did as she asked, and my hand worked gently up and down the length of my hard shaft. I squeezed at the base and tickled at the head, all in an effort to arouse me completely. I had a really good idea about how long I would last, but if I was going to stroke like this I’d be lasting a really long time. With my other hand I reached down and cupped my balls, and held them in my fingers, and then slid my fingers around to make a circle at the base of my balls. I squeezed a little. The pressure was there, the pleasure, and maybe a hint of pain. It was all good, though. I saw Jen’s eyes flare a couple of times, and her nostrils were definitely flaring. Her lips parted as she watched, and I saw that her legs were beginning to quiver a little. I figured that arousal was coursing through her now.
“What turns you on?” I asked quietly.
“This,” she said immediately, “watching you jerk your cock!” She smiled at me, whispering. “It’s making my pussy just throb right now!” I felt my abdomen muscles surge powerfully as my cock gave a hard lurch. I was glad that I still had my hands around my balls – I might have shot off right there without the stopper. “What does it feel like?”
“It just feels so good,” I said. “No way I’m stopping now,” I added. I felt another tingle of pleasure rush through me, and knew what that meant. I moved my hand to the base of my cock and squeezed in steadily increasing pressure. Once I had a really tight grip, I slid upward. Jen’s eyes focused on the head of my cock as the droplet of pre-cum oozed out and oozed and more until finally a very sizable clear drop was there. Jen, with slightly trembling fingers, reached out and swiped it up with her finger. She sucked it into her mouth and moaned as she did so. That was it for her; she spread her legs and her hand went to work.
The sight was powerfully erotic. She was rubbing her clit now, but would slide down into the folds of her pussy and spread her lips apart, showing me the pink. She looked glistening down there and I thought maybe I spotted a trail of liquid pulled by gravity down over her pink little butt hole. She rubbed her clit slowly, and was making these terrific little sighs and sounds of pleasure as she did so. The quiet ‘oh’ or the way her breath caught momentarily in her throat. I slowed down my jacking, wanting to try and pull off the big ending together!
“Don’t come without me,” she warned.
“No, that w-wouldn't’t do,” I panted. “But catch up,” I added.
“This is so fucking wild,” she thought. Her other hand had reached down and now she was doing the double fingering moves. One hand was busy on her clit and the other was slipping fingers into her pussy. “God I’m so wet and hot right now!” she moaned. “I’m close I’m so close!” she warned. I picked up speed although kept careful hold of my balls. I wanted to stem the tide of my orgasm for as long as I could and that was the only thing I could think to do. “Oh oh oh I’m g-gonna…” she moaned and I saw her face slacken as her head kicked back and mouth fell open. I released my balls and jerked hard, fast and then it was coming for me, too…
I grunted deeply as my first stream of cum ejaculated from my cock, shooting up slightly in the air and landing on my fist. The mess settled between my fist and my cock but I was still sliding my hand up and down and now I was aided by the slipperiness of my semen as I jerked and stroked and coaxed yet more come out of my cock. Jen was staring as much as she could at me, though her body was quaking and jerking and she was panting hard as her orgasm was still evidently ripping through her. I felt it finally subside, and now I had a mess. Jen smiled wanly at me. “Guess the cum-catcher’s a good idea, huh?” she said in a contented tone of voice.
“Yeah,” I agreed. “That was fun.”
“Yes it was.” She laid back on her bed, naked, her fingers still slowly tracing around her skin. “Very fun!”
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