College the experimental years

I was this fresh faced, naive, eighteen year old, from the midwest, typical from the area I grew up in....I had wavy blond hair, blue eyes, had a nice farmer's tanned body, athletic body from playing sports and working on the farm, lean muscled, narrow waist and a very nice bubble shaped butt (or that was what my ex-girlfriedn had told me). We had decided to break up the summer before I left for college. She was a year younger and we had been dating for just over a year. She was cute, funny, kind, and nice to everyone she met. She had a great smile, chubby, with perky breasts, and a big rounded ass. I lost my virginity to her on our third date. It was at a drive in theater in our home town. I drove a van that the back seat folded down into a bed. At the time, I thought we would watch the movie. My ex-girlfriend, Lynette, had other ideas. We watched the first of three movies playing that Saturday night. We sat close to each other under a blanket in the back seat of the van. I had the driver's window partiallwas down to accommodate the speaker. It was cool that night. I believe it was the last triple feature of the season. I had my arm around her and she huddled close to me. We had started kissing. Lynette reached down and began to rub my crotch. She easily got me erect. I moved my hand up under her T-shirt. Lynette wasn't wearing a bra! Upon my discovery, she unzipped my jeans and pulled me out. I had never considered myself hung before but Lynette had to pull the blanket back to admire my cock. She looked wide eyed at my cock and then at me with her green eyes. Lynette was a fair skinned redhead which matched her sometimes fiery personality. She gasped telling me she had not seen one so big before. I was half naked with a girl in my van..it didn't dawn on me that she had seen other cocks before. I took off her shirt. Lynette got on her knees between my legs. She put my seven and half inch, cut cock in between her breasts. She pushed her breasts together and I watched her bob up and down transfixed at the amazing site! Her pale breasts with very tiny nipples were so amazing! Lynette looked at me and smiled. I told her this was great, she replied,"if you think this is great just wait and see!" she began to suck my cock. Her luscious big lips went over my tip back and forth. My jeans were down around my ankles, my knees were open wide for Lynette to work on me. She broke for a moment to take my jeans off as I took my shirt off. We had only kissed on our first to dates and I wondered if this had anything to do with that cheerleader from the opposing team who came up to me at the end of the game to talk to me. No matter, I was enjoying it. Lynette had me so hard. She moved to her side and slid out of her jeans that made her ass look so good. Then she took off her white panties. Lynette asked me to convert the back seat into the downward position. We laid out a blanket over it. We got under a second blanket naked and laid on our sides kissing and touching each other. Lynette focused on my cock. I ran my hand over her breasts and down between her legs. She really liked me when I ran my fingers between her slit. Lynette had enough of the foreplay. She moved on top of me. She reached down between her shapely thighs and took my cock. Lynette lowered herself onto me. Her whole body shivered as she went down. She gasped and braced her hands on my chest. I was rubbing her hips and ass. Lynette went all the way down on me. She gave out this high pitched squeal for a moment then jerk back up off of me. I was puzzled by her reaction as her chest was heaving. Lynette took fast short breaths. Her body was trembling. "Holy shit!! You are so big!!" she began to rub my cock. I joked that is what all girls are supposed to say. Lynette shook her head adamantly that was not always the case she said. She couldn't stop touching my cock and admiring it. I liked it! I also liked touching and sucking on her big pale breasts with tiny nipples. They were so small that even erect the barely pokes out. Lynette got the courage to take me in once more. She now gushed as I my cock reentered her. She went slow, breathing very deeply in on the way up and out on the way down. Lynette cringed as she went deeper and deeper. She pleaded with me not to thrust as she tried to acclimate to my cock inside her body. She broke into a feverish sweat all over her plump body. I ran my hand all over her body and took everything in. I recorded how sexy Lynette looked, her curly long red hair how it hung down, her round breasts swaying from her erratic breathing, my hands caressing her large bulbous ass, and watching my cock disappear inside her body was so erotic to me. Even she looked down to watch. I told her how good she felt. Even though she was on top and her legs were straddling me, she began to get shaky. I got the feeling something wasn't right, I asked. Lynette looked at me, I thought she had meant to hide her face with her red curls that cascaded over her face. She was crying and visibly upset. I told her we could stop even if I really wanted to keep fucking her. Lynette moved off of me and collapsed next to me. She wept burying her face into my chest. I just held her quietly and told her we didn't have to do anything more. I then waited a few minutes as we pulled the blanket over us then told her I was a virgin. Lynette didn't believe me at first. This seemed to get her out the funk she was in. Lynette looked at me and began her inquisition. "How can this be? What about this one girl I had dated? Didn't you know that every girl in the school wanted to fuck me?" I told her with school, chores, and sports there wasn't really much time to do anything else. Yes, I was the quarterback of our high school football team, a pretty good baseball player, and ok baseball pitcher but I really was shy around girls I was interested in. Before Lynette, I had dated a popular girl at school, she was attractive, cheerleader but she was good girl who basically dated me for status. We had only ever kissed and held hands. As for every girl that wanted to be with me, I must of been pretty stupid and oblivious and took it as girls just being nice. It was Lynette who asked me out. I liked curvy girls, especially redheads and I thought she was hot. She didn't look or act like most girls at our school. Lynette wasn't into the popular crowd, she could hang with them but like me... I never seemed to feel comfortable with them. I had been questioned by some of my friends as to why I would want to date her. As Lynette and I talked, she seemed to warm up and was purposefully rubbing my cock again. We began to kiss softly. It heated up quickly. Lynette suggested that we try again but in a diffetent position. She got on her knees and leaned over the bed in the back of the van. I got behind her. Lynette shuddered as I moved my cock up and down her backside. She reached from under herself and spread herself open exposing her juicy pussy. The image is still burned into my brain! I put my tip in slowly. Lynette moaned and quickly begged for me to not go too deep too fast. I took shallow dips in and out. Her pussy made juicy sounds. Lynette told me it felt so good. There was a nervous tone in words. I also told her how amazing it felt to be inside her. I told how I enjoyed our two bodies becoming one. Lynette spun her head around, "are you for real???" I thought so and she joked that must be what I say to all the girls. Lynette laughed. When she did her pussy clamped on me! The contortion with each jerk as laughed made the experience even better. I began to feel really good. I took longer and deeper strokes. Lynette noticed. Her moaning got louder. I was hypnotized by how her sexy big ass looked from behind, the curvy from her ass to her hips and her lower back to her redhair swooped over her shoulders. In this euphoric state, I couldn't help but insert my entire cock into her. I shoved it in deeply. My cock felt like it had slipped into a smaller tube, she was extremely tight! Lynette cried out blending pain and extacy. She fell forward as I went with her in order to keep my cock fully buried. She let out this hoarse yelp. "Too Deep, Too Deep!!" she groaned. I backed out and apologized stating how sexy she looked and I couldn't control myself. Lynette was quick to quip back asking if I thought what I had just said would work on her. I paused and before I could answer she interjected, "Well, you're right!" She let me in once more and this time it was savage. Lynette backed into me and I thrusted hard into her. My flesh smacking into her jiggly ass. The ripples of her flesh from her ass up to her lower back were mesmerizing! When it was time, i had fought back the urge to cum as long as I could. I held onto her hips, fully implanted, I erupted as my body jerked violently as I pumped my cum deep inside Lynette. She moaned as I grunted. I stayed inside her until every aftershock had passed. We moved up on the bed and she wrapped a leg over me as we looked into each other's eyes. I don't think my eyes were ever as big as they were. I saw Lynette as perfect in that moment. She glowed! Later she would confess how happy she was in that moment. Both of us sweaty and breathing fast and hard. Both in awe of what had happened. I didn't say it but I was glad that Lynette was my first..

The sex was amazing after that too! We didn't do anything crazy but it usually ended with me cumming inside her. When I graduated high school. Lynette wanted to get married. I wasn't ready and was looking forward to going to college. It caused a fracture in our relationship that summer. Lynette gave me an ultimatum either we get engaged or break up. I didn't appreciate being put into a corner and so broke up with her. I wished we could of stayed friends but she went publicly that she was pregnant. I was stunned and ashamed when I told my parents. They talked to Lynette's folks. It came to light that Lynette had lied just to try and get me back. I never talked to her again after I left for college.

I had chosen to attend a college that was on the west coast I am pretty sure it was a shock to most people from a small town to attend a big college but I kind of liked that I didn't stand out here. I moved into my dormitory and was informed by my resident assistant that my roommate would not be coming. It made a few of my newly acquainted friends jealous. The first few weeks of college were just trying to find a routine and exploring my new surroundings. I quickly discovered that there were many guys that were superior athletically to me. I made friends with guys on my dorm floor and through pick up basketball games at the rec complex. The girls at college were sexy and plentiful. Most of my friends were single so it was an on going competition to see who would hook up first. I really had no game when it came to dating. So when I had the courage to ask this cute blonde girl from one of my classes out, she turned me down politely. Stating she had just started seeing another guy. It didn't hurt as much as I had planned. It may seem odd but failure was probably one of the best things to happen to me. Because I knew my answer instead of playing it in my head of "should I ask her out or shouldn't I??"

It came as shock when one of my new friends had come out as gay. I wasn't well versed in the as I came from a small conservative farm town and was commonly told 'sheltered' from the world. They were right, I didn't know much. But I was curious.

It was the early part of the 1980's. I began to ask him lots of questions. The more we talked, the more I thought he was telling my story. He was a good athlete in high school, he was in the popular crowd, dated girls to hide that he was gay, how he never seemed to fit in with anyone, and shared his first time with a guy. As he told me, I found it erotic and I had to shift to hide my erection it gave me. While most of my new friends drifted away from him we continued to go to class and workout at the gym together. He was bigger, stronger than me which made him a great workout partner. I just assumed he would eventually hit on me but he hit me with a left hook when he flatly told me I wasn't his type. I can't fully explain the hurt but I had felt a bit jaded. Even more than when a girl wasn't into me. He took me to an adult book store in a seedy part of town. I saw a man getting a blow job from and older guy. I saw another creepy guy jerking off a young college aged dude. There were loads of gay magazines, videos, and toys. I couldn't control my cock as it grew in my shorts. My friend bought me a magazine because I was too chicken too. I took it back to my dorm and masturbated like never before!

I told my friend that while I looked at the pictures of these hot sexy guys, I became infatuated with the sensation of them being inside my ass. It both terrified and aroused me on an insane level! I asked him how do I know if I am bisexual or even gay. He suggested I get a dildo or anal beads and see how it would feel. He told me how I should prepare myself. My friend took me back to the adult book store. I bought a dildo and some small anal beads, a string with four balls. He told me to buy baseline for lubricant and a enema to clean my ass. The guy at the counter could tell I was newbie and told me to have fun. I felt a little ashamed as I heard two guys going at it hard in one of the small private rooms in the back. Out by my friend's car there was a guy giving oral to a heavy set younger guy by a dumpster. We left after watch the two for a minute. As he drove us to get the lube and enema, I inquired what anal sex was like. He told me his first few times hurt like hell which was normal but it does begin to feel more pleasurable.

I went back to the dorm and administered the enema into my ass. Minutes later I bolted from my room to barely make it to toilet in time. I had never had such a strong urge to push out of my ass. I felt a bit funny afterwards and lightheaded. I walked back with a towel wrapped around my waist. It was later in the afternoon, the sun was shining through my window. I laid my towel out in the middle of the floor. I put the anal beads, dildo, baseline, and a small towel on the towel. I knelt down on my knees. I dipped my finger into the lubricant jelly and stuffed a finger into my ass. It was a rush! Just my finger going up into my ass felt strange and electrifying. I moved it around and removed it slowly as my ass tried to push it out. I took two on the next visit. My tight hole fought the violated sensation of something going in the wrong direction my ass had been accustomed to. Once I had tried to stretch my hole with my two fingers, I lubed the anal beads. I stuck one then two then three and four. I began to worry what would happen if the string broke that connected them. My friend had told me to masturbate and when I was close to pull slowly on the ring having the balls pop out of me one at a time. I laid on my back, positioning the magazine I had previously bought. I looked at this hot sexy tan man with a beautifully large cock. My legs were open as I jerked hard on my cock. I was so hard that I thought I my burst. I imagined being fucked so hard and how it might feel to have a real cock in my ass. I rubbed one hand over my erect nipples and I got closer. When the surge was too much. I pulled the ring. I shot an incredible load up over my head as one bead popped out, the second load was impressive still able to shoot over my head and some landing on my face with the second bead, the third and fourth produced a good amount of juices that splattered my chest and abs. My cock was still rock hard. I ran fingers through my cum and tasted it. It was bitter but it didn't deture me from trying more. I was super charged! I sat up and placed the dildo onto the linoleum floor. It was a nice cream colored six inch dildo, somewhat thick. I lubed it up and positioned myself over it. The tip touched my hole and I flinched with anticipation. I began to wonder if I would be this excited if it was real. I sat down and forced it into my ass. As it entered my ass, I pushed it out as hard as could. My body was involuntarily trying to extract it but my horny mind wanted it much more. It passed through in me and I let out a light toned moan. I sounded feminine in that moment and it startled me. I sat further down. The dildo felt bigger inside me. My tight hole clamping down. The dildo penetrated past my ability to push it out. My body began to shake as I tried to 'get comfortable' with a dildo in my ass. My cock was rock hard even with jerking off. I moved very timidly up and down on the dildo. My cock bounced. The suction part of the dildo didn't work as well as I had hoped. It came up with my ass hole clamping it in place. I stood up with it in my ass. I looked in the mirror admiring and getting turned on by the sight of it stuck in me. I went to my bed and proceeded to fuck myself with the dildo. I moaned lightly as not to have my neighbors through the paper thin walls heard me. I had my legs up as I reached down and struggled to grip the dildo covered in lube. I felt strained and dehydrated, my legs shook, while stuffing it deeper and deeper. Loud farting sounds echoed in my room from pockets of air escaping me. As I grew closer and closer, I supplanted the dildo as far as I could even with this new sensation i was feeling. I ejaculated hard with little juices but as I was Cumming my dildo was pushed out. It fell to the floor and a emptiness consumed me. I wanted more! !