My First Semesterbytk998877©
As a 48 year old married bi man, I often think about my first experience with a man. This is my first story and I hope someone enjoys reading it as much as I enjoyed living it.
My first semester in college I was worried about what kind of roommate I might have like most people on their first time away from home. I spent 3 nights by myself in the two man room before my roommate, Shane, finally showed up. It came out later after we got to know each other that he was worried as well and was spending the nights at a frat brother's room before he got enough nerve to show up. We had become good friends by then and had a good laugh about it.
My girlfriend in high school, Bettye, had gone off to join the Army before the first semester started and I was there all by myself. Shane had a girlfriend as well but she was several hours away, so we became very close and did about everything together.
I had just turned 19, 5'9" and at the time probably 170 lbs, in pretty good shape from playing football and running track in high school. Shane was about 2 inches shorter than me with long brown hair and a stocky built. I had never thought of being with another guy sexually before and, as I found out much later, it never occurred to me that he was bisexual. Knowing what I know now, I wish I picked up on it then. We could have had even more fun than we did!
Most weekends, we would run to the gym, work out with weights or play handball, and then sit in the sauna for awhile. Afterwards run and pick up some beer/wine and see what was going on at different parties around campus before getting back to our room.
On one particular time after the sauna, I was in a shower stall, and having to piss really bad all of a sudden, I just let it go in the shower. Evidently, there was a man in the shower stall next to me and he must have known what I was doing. "Looks like someone had to really go" I heard. Embarrassed, I stopped and quickly finished, trying to get out of the shower room before I was noticed by him. I had my shorts and shirt on, just finished getting my running shoes tied when out he steps. A much older man I thought, probably close to 50. I knew he was watching me as I bent down to act like I was tying my shoes that were already tied. He just stood there awhile until I finally had to raise up.
"I, uh..." He was standing there in the nude in front of me, not even making an effort to reach for his towel. Taken back by that, I tried to finish as best I could.
"I uh, am uh sorry about the peeing thing, I just couldn't hold it much longer, and I..."
"That's OK, don't worry about it, can't say I haven't done the same thing before" smiling at me, still not reaching for his towel. "Sometimes men have to do what men need to."
"I, guess so" I think I said, embarrassed by it all. Standing up I got out of there as fast as I could, found Shane and said "I'm ready, are you, let's go."
Shane and I hit the store and he got the beer as usual having the better fake ID and being a year older. We headed back to our room before heading out that night. He could tell something was on my mind as I wasn't talking as much as usual.
"What's up Terry, you seemed in a hurry to leave the gym today? Everything alright?"
I told him what happened and how embarrassed I got. Shane started laughing, asking if I was ever going back there again.
"I'm not sure, I don't think I want to run into him again, there is no telling what he thinks of me after what I did."
Shane looked at me funny, "Are you kidding? You think he is thinking badly of you?"
"I don't know, maybe."
"Man, sounds like he was hitting on you if you ask me."
"Look, first he tells you not to worry about it, second you said he was smiling at you, third men have to do what men need to do or whatever, and most important, he just stands naked in front of you. You may not know this, but believe it or not, some guys hook up that way."
I blew it all off and after several beers decided I was too tired to go out and went to bed. But I couldn't get to sleep. I kept thinking about an older man standing nude in front of me and him wanting to hook up with me. I was getting aroused thinking about it and couldn't stop. I kept trying to recall more details of him. I remember he was taller than me, not overweight at all, with graying brown hair. Now that I thought about it, he never took his eyes off of me that I could tell. I remember looking at his cock, not staring but my eyes just went there for some reason. His looked to be about the same as mine, but he was not fully erect. What if he wanted to get together with me? No, that would be silly. I wouldn't know what to do anyway. I guess he would let me know. This is crazy, I have a girlfriend anyway. I was very horny and I couldn't see or even call Bettye, so I just jacked off thinking of her but images of him came to mind occasionally.
I woke up the next morning and went for a run. The first thing that came to mind was him standing in front of me naked. I tried to get it off my mind as I ran. Coming down a slight hill in front of the admissions office, someone stepped onto the sidewalk which I did not see until I was right on them. Almost stopping immediately and moving to the side to go around him, I caught him by surprise as well.
"I'm sorry" I heard.
"That's ok, no harm" looking up and of all people, him. This time I didn't run.
"So you must exercise every day?" he asked.
"As much as I can."
"Listen, I hope I didn't embarrass you yesterday, you seemed a little shook up, I didn't mean to" he said.
Playing it off, "Oh no big deal, don't worry about it."
"Well, regardless, I don't want you to have a bad impression of me, let me make it up. I'm Steve by the way; you wanna have breakfast, my treat."
We ended up in the school cafeteria, but I was too nervous to eat anything, so we both just had coffee and talked for an hour at least. He was pretty cool, even being 30 years older. We talked about high school and college plus Steve gave me some helpful tips about studying. I told him about my girlfriend being gone and being new here. He was a history professor and lost his wife 5 years ago and moved here this year and understood about being in a new place without someone to be close to. He had a son, but he lived across the country and didn't get to see him but a couple times a year. He told me his house was just off campus a few minutes from here and if I ever wanted to stop by on the weekends or needed a place to hang it would be fine with him. There was a pool out back if I or a couple friends ever wanted to use it. I started to think he was hitting on me and I felt my dick start swelling a little. I wanted to see if Shane was right and somehow felt brave enough to ask him to show me where it was if he had time.
We walked a few blocks and stood out front of a nice 2 story brick home.
"Well, this is it, if you ever want to stop by." I noticed him looking at me with that smile again like in the shower room. I think Shane was right.
"Well, I don't have any plans until later today; you can show me around the place if you like." My heart beat a little faster as he said great, come on in.
I sat down on the end of the couch and Steve sat on the other end. He asked me if he could get me anything and I told him some water would be great. He got up and went in the kitchen. I started flipping through some of the magazines on the coffee table, National Geographic, Smithsonian, Newsweek, and on the bottom was a Playgirl! I thought it might be something his wife had read but it was a current edition. The cover was showing when Steve came back in with my water. This time he sat in the middle of the couch, closer to me.
"Here you go Terry" handing me the glass. Steve froze for a few seconds realizing I had seen it.
"Oh, that, I guess you're wondering what that's doing in there."
"I have something I need to explain to you, I did kind of plan yesterday in the shower room. I saw you working out and when you went to the shower, I kind of picked the shower next to yours."
Shane was right.
"I hope you don't think poorly of me, it is just since my wife's passing, I began having thoughts of being with a man, trying it out. I find the man's body very sensual and sexy. Maybe it's a midlife crisis thing, I'm not sure. I saw you working out and I found you very attractive, please don't be mad."
I was taken by surprise by that and didn't know exactly how to respond. My hands started to sweat a little. Many thoughts were running through my mind at this point. Thinking back to Bettye and being faithful to her, if Steve and I do anything it really wouldn't be cheating on her. My heart beat faster. Maybe I could fool around just a little with Steve; I wouldn't be cheating with another girl. I looked back into his eyes.
"I'm not mad, it's just I don't think of myself as attractive to other guys, I told my roommate about the shower situation, and he thought you were trying to pick me up, I didn't believe him though. It's just I have never been with a guy before, I'm not sure what to do."
"Listen Terry, you can leave if you like, I will understand completely, but you are a very attractive young man. I won't bring it up again if you're uncomfortable."
I thought about leaving but a part of me wanted to stay even more. Maybe it was not having any sex for the last 2 months, but I started to feel my cock stirring in my shorts.
"Steve, I'm not sure what to do to be honest."
Seeing an opportunity Steve moved closer, sitting right beside me. "Well, we can take it slow, if you ever feel uneasy about anything, we don't have to go any further. But you're always welcome to stop by."
With that he put his arm up on the cushion behind me. "Is this too much."
We sat like that for a minute and had some small talk. I could feel his knee up against mine.
"Is this to close?"
"No it's ok" I got out somehow.
Steve then reached over and placed his hand between us against my outer thigh. My mouth was feeling dry from being nervous; I sipped some water and leaned forward to place it on the coffee table. Sitting back his arm moved down across my neck, the back of my head cradled in his elbow and his hand moved onto my thigh. I looked down at his hand.
"I think so."
My heart beating faster, my cock growing harder. After a few minutes, we both looked up at each other, he smiled again, reaching down with the hand around me, he started rubbing my upper arm. I finally got comfortable enough to smile back. Steve leaned over towards me and softly asked if he could kiss me. I had only kissed my girlfriend before. I softly said yes. He placed his right hand against my cheek turning my face to him and leaned in towards me. I closed my eyes and then felt his lips press against mine. It was softer than I thought it would be. I felt his hand rubbing my thigh and felt his warm breath against my face. It did feel nice. I relaxed my lips and started to enjoy the moment, kissing him back. Eventually our lips parted and felt his tongue softly exploring my mouth. I was being French kissed by another man and was enjoying it. We both started breathing heavy as his hand moved from my cheek down to my neck. He pulled a few inches away from my lips.
"Was that ok?"
Yeah I whispered.
"Do you want to leave?"
"No this is OK" I said softly.
Steve looked down and noticed the bulge in my shorts. He leaned down and as he kissed my cheek and neck whispered in my ear.
"It looks like you're enjoying it as much as I am."
His hand started moving in between my legs feeling my hardness. I looked down and watched him rub his hand over my crotch making me even harder.
"If you want, we can move to the bedroom, it might be a little more comfy."
I wasn't sure what to expect, but wanted to find out. At least I wasn't fooling around with another girl; I wasn't cheating on Bettye in my mind. All I could do was whisper ok. We both stood and he held my hand and led me into his bedroom. We stood by the side of it and Steve put his arms around my waist and pulled me into him, his soft lips pressing against mine. I started to feel at ease in his arms and placed mine around him against his back.
"We can take our clothes off if you want. Just as much as you feel comfortable with."
I kicked off my running shoes and slipped out of my running shorts and watched as he undid his belt, unzipped and let his pants fall to the floor. I held onto his arms as he stepped out of them. He unbuttoned his shirt and took it off, exposing his still well built chest with mostly dark with slight graying hair. I started to take my shirt off, but Steve put his hands on mine, taking the bottom of the shirt from me. I felt his hands rub against my sides as he pulled it up and over my head.
He got into bed and put his hand out for mine and pulled me onto the bed beside him. We lay facing each other, one arm propping our heads up and Steve placing his other hand on my waist. He moved closer against me moving his arm under my neck and placing his hand against my shoulders. His soft kissing was tasted sweet. I felt his bare thighs against mine, my smooth stomach and chest rubbing against his hairy chest and stomach.
Not knowing what to do next I finally got brave enough to reach down and touch his cock. I had touched mine many times but never another one. I wrapped my hand around it and moved my hand up and down. We decided to take off our underwear and moved back into our embrace. Now our hard cocks were rubbing against each other. He totally had me by this time.
"Can I kiss you down there, Terry?"
His lips touched my cock and it twitched. His tongue that had been in my mouth moved up and down my shaft. Then I felt his warm mouth surrounding all of me. I closed my eyes, this was so much better than when Bettye sucked me. I looked down and watched as another man sucked on my cock, his head moving up and down, occasional slurping noises. I felt a finger move down across my balls to my rectum and move in circles around it. I had no idea it was that sensitive. It didn't take long before my balls started to unload. I told him I was about to cum, but he just kept going. Bettye usually pulled off of me and stroked me until I came. But Steve kept me in his warm soft mouth. My hips started thrusting quickly as a large load shot into his mouth. I watched as some dripped from the corner of his mouth running down my shaft. As the next stream shot out, Steve tightened his lips around the base and I could see him swallowing, taking all of it. Another first for me. I never knew it could feel this good.
Steve rose up and looked at me, that wonderful smile again. He asked if I was ok with everything so far. "Oh yes" I said breathing hard. He bent back down and licked up what had spilled out and run down my balls, gave my cock a couple of kisses on the head and moved back up into our embrace. We both smiled and laughed a bit. He moved towards me and we kissed again. He tasted different this time. I could taste where my cum had been in his mouth and I was getting turned on by it.
His fingers ran through my hair and he started kissing my neck and behind my ear. He told me I didn't have to but that I could kiss his cock if I wanted. I told him I would try but I didn't think I would be as good as he was.
"Just take your time and only do what you feel comfortable with."
I moved down to his cock. It was cut like mine and was much bigger up close than the quick look I had outside the shower. A large mushroom shaped head like mine but maybe 1 ½ inches longer. My fingers wrapped around it, barely able to touch my finger tips. Except for the length, Steve was about the same size as me. His hairy sack hung low between his thighs. My heart was really beating fast now. I was about to taste my first cock. I started by kissing on it. Starting with the head and then down the shaft. I really didn't mind the taste or feel of it like I thought I would. At first I just held the swollen head in my mouth and got used to it. I could tell Steve wanted more of himself in my mouth, his hips thrusting upwards. I laid my head down on his soft hairy stomach and moved my mouth down farther onto him. I tried to do what he had done, sucking on the way down and a little harder on the way up. I did this for about 15 minutes without him cumming. I was afraid I was doing something wrong. I stopped and looked up at him.
"Am I doing it wrong, it doesn't feel good does it?"
"No, no, Terry, you are wonderful, it's just as you get older sometimes it takes a little longer to get there, it feels unbelievable! You are doing great."
I moved back up and lay next to him and told him my jaw was getting a little tired and asked him if he wanted me to jack him off. He told me I could do that or we could try something else. I thought it was only right if I could return the favor for him. We kissed some more and in between kisses I asked what I could do.
"You know when I was sucking you and I had my finger around your bottom?"
I leaned up from his face, "You want to put it in me back there?"
"Terry, you have no idea how much I want you! I have never been turned on like this by anyone but my wife."
"But Steve, I have never... you know. I want to try but...how does that fit in there?"
"We can try, only if you want, and if it doesn't work, so be it."
"Well, I don't know. If we did do it, what would be the easiest way?" laughing a little.
"If you get on top of me, you can be more in control of how much goes in."
I looked down at his hard dick and thought about it. I really was getting into it by now and said ok. I straddled his waist, my bare thighs on his hips. I could feel his hardness slipping between my cheeks.
He explained it would be easier with some lube so he reached in the nightstand and got a tube of Vaseline. He said I should put some inside of me so I took some on my finger and reached down and slipped it in me as he held my ass cheeks apart. He told me to put plenty on his cock and I did. I lowered myself back into position. I spread my ass for him as he took his hand and guided his slick hard cock to my opening. Closing my eyes I lowered onto his cock as I felt the head pressing against my hole. There was a sharp pain and I eased off him. We tried that several times but the head never got in. I felt his cock head pressing above my opening and then felt his thumb slip into me working it in and out till it was moving in easier. Steve pulled out his thumb and replaced it with his dick.
I was spreading my cheeks as wide as I could, my eyes closed and I felt the head start to enter me. I lowered a little more, he pushed upwards and I felt it get pass my virgin ring. The pain was intense but I held myself on him this time. My hands left my ass cheeks and I leaned forward and placed them on his chest. Finally opening my eyes, we looked at each other.
"I think it's in" I said.
"Are you ok?"
"Yeah, let's just stay like this for a minute."
"Whatever you need Terry, lean down here to me."
I moved my lips to his and we explored each other's mouths with our lips and tongues again. Steve's hips began to rotate in small circles under me and I could feel a little more going in. A tear rolled down my cheek and Steve reached up and brushed it away.
"Are you sure you're ok with it?"
"I am, it isn't as bad now, it's actually feeling better."
"Rotate your hips in a circle with mine."
I did and after 10 minutes of this all his cock was nestled deep inside of me. I started to move my hips up and down and we got into a really good rhythm.
"Oh Steve, I can't believe your fucking me?"
"Terry, you and I are making love."