CHAPTER 8: The all nighter
When we got back to the room Jay and I both stripped to our underwear. It was the usual uniform for the guys’ dorms. We sat silently for a few minutes before Jay spoke.
“So you want to talk about tonight?” he asked. I did and I didn’t. I had raised my hand about having had fantasies involving other guys. Jay had raised his hand first. I decided to shift to a safe subject.
“Jack is certainly full of surprises, isn’t he?” That seemed pretty safe, and kept the conversation off of ourselves.
“He’s very frank about having done stuff with other guys. He let Helen jerk him off in front of us. I don’t get any vibe that he’s coming on to me or you, or any of the other guys in the dorm. He kind of flirted with Drew there at the end, but made it clear that nothing was going to happen anytime soon.” I waited for Jay to say something.
Jay replied. “I’m kind of confused here. They never answered Craig’s question about whether he might be gay. I’ll bet more guys than those of us who raised our hands have had some kind of dream or fantasy involving guys. I’m like Jack, I really prefer women.” My turn.
“Me, too. But is that a preference instead of an absolute commitment? Jack made it clear that his was a preference. He doesn’t rule out doing something with another guy.”
Jay sat in silence for a while. “My Dad, the shrink, talked to me about sexual orientation. If he ever had any issues with it I have to assume they’re resolved. Then again, he’s in his late forties. Dad said that people who are 100% straight or 100% gay are actually the minority. Very few people are truly bisexual and have exactly the same attraction to both sexes. Most people who claim to be bisexual actually prefer one gender or the other.”
“Dad told me that most people are somewhere on a sliding scale between straight and gay. And most of those people are real close to the straight end. I mean, just think. If they weren’t the species might die out.”
My turn again. “True, but is sex all about getting off or making babies, or is it about other things, too? Harold’s Dad told him the best sex was with love. Have you ever loved someone?”
Jay admitted that he hadn’t. His high school girlfriend had been fun and he enjoyed the sex. He’d had sex with a bunch of girls before he got here, but hadn’t felt love for any of them. He paused then, started to speak, and then paused again. This went on for a couple of minutes. I just waited patiently.
“The closest thing I’ve had to love was probably my best friend in high school,” Jay finally admitted. “We did almost everything together. We even fucked our girlfriends in the same bed. All of our interests were the same. If I wanted to hang out it was with him, not with my girlfriend. She was all mushy and lovey and I couldn’t stand that.
“We double dated. We went on trips together. We went camping together. We never fooled around with each other. If he had initiated it, I have to be honest. I don’t know what I would have done.”
Jay stopped for a minute and then continued. “The last camping trip we took was shortly before I came here. We were by ourselves in the woods near a lake. We went skinny dipping, something we had done a lot with each other and with our friends. This was different. We horsed around in the water, splashing and dunking each other and acting like ten-year olds. When we got out of the water we both had erections. I know Jerome said that it’s natural to get a boner around other naked people, but I didn’t know that then.”
“I tried to cover up my dick but Garrett said it was OK. He was hard, too. We dried off and went into the tent. Neither of us got dressed. Finally he asked if I wanted to jerk off with him. So, we jerked off together. We didn’t jerk each other off. It’s possible I would have done so if he asked, but he didn’t. We each slept in our own sleeping bags that night and never talked about it again.”
This was getting pretty deep. We were revealing secrets about ourselves, and it was my turn to reveal.
“I had a similar experience. Five of us guys always hung around together. One of the guys had a pool in his back yard. We would have sleepovers at his place and go swimming naked if his parents weren’t home. One night one of the guys said his dick was bigger than anybody else’s, so we compared. He was right. Then he started jerking himself, so we all did. When he was hard he was still the biggest. Then we all gathered in a circle in the middle of the shallow end of the pool. I don’t know what came over us, but all at the same time we each grabbed the dick of the guy on our right. I wouldn’t let anybody touch my dick, so I dropped out of the circle. The other four guys jerked each other off.”
“So, what did you do?” asked Jay. I wasn’t sure I wanted to tell him, but this was a night to come clean with my roommate.
“I jerked off by myself fantasizing that I was part of the circle. The guys came one by one. I came somewhere around the middle of the group. I regretted that I had been such a prude and wouldn’t let another guy touch my dick.”
“The truth is that I kind of regret not taking part. We were all friends who had grown up together. We had seen each other naked on many occasions. The other guys had jerked off in front of the group but I never did. If I hadn’t been such a prude, I wonder if I would have had my first experience with a guy.”
We continued for hours sharing secrets about ourselves. Some of them were silly, some were pretty deep. The sun was starting to come up when Jay went over and locked the door.
We said nothing. After a minute Jay’s hand was on my leg. I put it on my dick, and took his hard-on in my hand. Without saying a word we jerked each other off, both of us cumming on my sheets. It was time for laundry anyway, so I didn’t mind. I felt incredibly close to Jay at that point. I really would rather have been fucking Janice, but she wasn’t there. I thought that maybe this is what Jack meant by a preference.
Jay kissed me on the lips, so I kissed him back. It was more than a brotherly kiss but less than a romantic one. We then fell asleep, snuggling together naked in my bed.
When we woke up the next morning we were still naked in bed together. Jay spoke first. “I’ve never done anything like that before. We’re being completely truthful with each other, so I’ll tell you I enjoyed it.”
I couldn’t stop myself. “I enjoyed it too. I really want to fuck Janice, and probably a lot of other girls. I don’t get turned on looking at you, but that was really great.”
Jay replied, “We’re not going to schedule anything like that, but if it happens again it happens again. Now, get your sorry ass into your swimming suit and let’s hit the pool.”
I never did figure out why we wore our swimming suits to the pool because we always had to swim naked. As we were taking off our suits Jack and Helen walked up. Jack was in his omnipresent striped boxers. Helen wore a sports bra and cut-offs. She got naked and dove in; Jack removed his boxers and followed her.
Helen asked me and Jay how much we knew about female masturbation. I didn’t know much about female anything and said so. Jay said that his high school girlfriend used to masturbate, but would never let him watch. Helen offered to hold a demonstration class.
She sat naked on the side of the pool while her “students” gathered around. Jack sat by her side. “Girls are luckier than guys. Some girls can masturbate just by squeezing their legs together. When we go into a restroom we get to close the door on a stall and get in a quickie. And we have toys we can use as well.”
All of this was new to me, but Jay already knew some of it. Helen continued. “If I want to masturbate I usually lay back slightly. Jack, would you support my back?” He did so.
Helen went on. “Then I take two fingers and stick them in my pussy. Like this.” She showed us. I was in awe and was starting to get hard. “Sometimes I’ll use three fingers. I move the fingers in and out, and I rub my crotch. That gets things lubricated and I start getting turned on.”
Jack was only semi-hard, but I was like a rock. From Jay’s labored breathing it was pretty evident he was also. “Now, as I get aroused my clitoris begins to grow. It’s sort of like your penis; it’s made of erectile tissue. The blood flow into my clit increases and it gets bigger. Now I can play with it and tweak it with my fingers.”
All of this was getting too much for me. My hand was under the water, and it wasn’t because it was too dry. I could detect some movement in Jay’s shoulder. He was probably doing the same thing I was.
“Now, when I’m really turned on I like to turn the action over to somebody else. Jack, will you assist?” Helen lay back and spread her legs. Jack replaced her hand with his and began massaging her crotch, letting his fingers enter her and probe. I was the student, why didn’t I get to practise?
“Once I’m really turned on I like to have a tongue take the place of the fingers.” Helen was nothing if not direct. Jack obliged her by slipping into the water and lowering his mouth onto her pussy. We got closer to get a good look. Jack withdrew and offered me his place. This was a completely new experience for me. I put my mouth to her pussy and started sucking.
“No, no, Mark, use your tongue to lick at my pussy and to penetrate my vagina.” I didn’t need to be told twice. I licked her pussy lips and let my tongue explore inside her cunt. The taste was slightly unpleasant, but I figured I’d get used to it. My tongue encountered something sticking outward. That must be her clit. I licked around it, and was able to bring it up to my teeth. I nibbled lightly on it. Helen moaned, shuddered, and began to drench my mouth with her juice. I had just given a woman an orgasm with my tongue.
I started to withdraw, but Helen’s hands gripped my head and forced my mouth back onto her pussy. I started licking and probing for all I was worth. I tried nibbling on her clit for a bit, but wasn’t rewarded with another orgasm. “Next,” said Helen.
I stepped back and Jay took my place. Jack high-fived me and said it had taken him a week to give her the first orgasm with his tongue. Now he was able to do it almost every time. The girls in Helen’s dorm used to invite him over for a “cat dinner” party. That’s when a bunch of guys would line up and eat pussy until all the girls had experienced at least one orgasm. He tried talking to me about technique, but I was off in fantasy land.
Just a few days before this I had been a virgin who was frightened of letting a girl see me in my underwear. In the past few days I’d had several blow jobs, fucked a girl from in front and behind, eaten a pussy, and jerked off my room mate. I decided not to think about the last one.
When we were finished Helen wanted to play out a fantasy. That was fine with me. Jack would fuck her while she and Jack simultaneously jerked off Jay and me. I figured if I didn’t think about the fact that for the second time in a few hours another guy was jerking me off, I’d be fine. I was fine. So was Jay. When we came Helen brought her hands and Jack’s up to her mouth. She licked all the cum off of the fingers. Jack high-fived both me and Jay.
We put on our suits and returned to the room to dress for dinner. In the dining hall we encountered Harold and Charlene. Charlene had great news: Harold was no longer a virgin. Harold blushed and grinned at the same time.
The rest of freshman week went about the same way. Classes started and the boozing and non-stop sex had to get toned down. Janice and I only fucked once a day. Jay started regularly dating a sophomore named Valerie. Taking Charlene’s advice to heart, we wore clothes around the campus and underwear in the dorm.
