Where it happened: A college fraternity room
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I just wanted to write about my very strange early experience as far as my hymen was concerned. I was a late bloomer and didn’t have sex until the summer of my junior year in high school. I met a boy named Tom at the mall who asked me out and we progressed to the point where he became the first boy I had intercourse with. I was scared and excited at the same time while Tom was smooth and experienced. Well as I quickly learned, I am very multiply orgasmic and my vagina is almost always in a state of arousal and wet, so my first time went very well without any pain. (I had come once already from just stimulation to my breasts, twice from fingering, and once more from oral sex before he ever entered me.)
Tom and I had a long relationship that lasted until I went to college. I went to an all girl’s college. There was a nearby engineering college where we girls would all go to meet boys and hang out at the fraternities. It was there that I met Dave. Dave was from a town near where I lived and we fell for each other rather quickly. He was a very good lover. My constant state of arousal and horniness led to a very active sex life with Dave. We experimented a bit and even almost had a threesome with Dave’s roommate Phil.
Phil was still a virgin. He was very cute, but overweight and not very sure of himself. I know that as cute as he was that he could have been laid many times over before coming to college if he had only had more self assurance. I liked Phil a lot and he was one of my best friends. In fact, he and I had started to fool around a little about a year after we became friends, even though I was dating Dave and still wanted to stay with him. Phil’s innocence and curiosity made it a lot of fun to play around with him.
Phil was a natural. The very first time we fooled around, he gave me four orgasms, two from just fondling and sucking my breasts and two from fingering me. The second time we fooled around, he went down on me and I swear he was a pro even though he had never done it before. I can’t remember how many times I came that time, but I know it was probably more times than I have ever cum in my life. The next time we got together, I undressed him for the first time to give him a hand job (I had not yet progressed to giving oral sex in my own sexual education.) What a surprise, he had an extremely thick penis. It was much thicker than either Tom’s or Dave’s, but it wasn’t quite as long as either of them. I had heard about big ones, and for the first time I had my hands around one.
We had progressed to the point where I asked Phil if he wanted me to take his virginity. We discussed it a bit because we needed it to be as secret as our other activity so Dave would not get upset. He was not sure it was a good idea since Dave was a very good friend of his, but he did finally agree. We made a plan to do it a couple of weeks from then when Dave was going to be home so we would have a room for a long time without interruption. I was during this brief time that I had an idea that perhaps if I could convince Dave to have a threesome with Phil that I could have my cake and eat it too. It would open the door for Phil and me to just have sex while I could stay in my relationship with Dave.
Since Dave and I were in an experimental phase, he thought about it but wasn’t too sure. I expressed the fact that Phil was still a virgin and it might be an interesting first time for him. Dave asked me if I thought Phil would think poorly of us if we asked him this because Phil may be saving himself for religious reasons. (I, of course, knew better but had to play like I had no idea…) I said let’s play it by ear.
The next night, we were all in the room together and we were just sitting around talking. Dave and I had planned to try the threesome that night and I had not had a chance to talk to Phil, so he was clueless about our plans. Dave and I did work out a signal that we would use if either of us became uncomfortable with the situation, either because we thought it was going to push Phil too far or because we were thought it was going to be too much for one of us. We were all sitting on the sofa in the room (it was one of two very large rooms in the fraternity that had been built for another purpose, but were now just sleeping rooms) just talking when I gave Dave the signal to start. He already had his arm around me and he started to give me a French kiss. Phil just sat there and kept talking, but watched.
Before I go on, I need to tell you that as part of our previous experimentation, we had already asked Phil to stay in the room down below while Dave and I were making love in the loft because it added a bit of excitement to our sex life. As a good friend, Phil agreed and had done this many times, and had even masturbated in his bed underneath the loft while Dave and I were going at it. When he was doing this, we could hear the bed moving and his moans and grunt as he came. It almost always put me over the edge for an orgasm, one of the two or three I would have while Dave was pumping away.
So Phil was not uncomfortable when Dave started to make out with me on the sofa while he watched. Then Dave put his hand on my right breast and started to massage it. This was the first time we had done more than kiss in front of Phil, and was part of our plan to get Phil involved that night. Phil stopped talking and watched. I saw the lump in his jeans grow. I asked Phil if he wanted to rub himself while he watched. He moved his hand to his crotch and gave himself a squeeze and adjusted his penis but then stopped. Dave then asked Phil if he wanted to work on my other breast. He took a deep breath, and started to massage my other breast. I had an orgasm the minute Phil touched me. Dave explained to Phil what had just happened and that I would probably have several orgasms before we finished. Dave was trying to be instructional to Phil who he thought was a complete virgin who had never even touched a girl before. (Of course Phil already knew all of this already, but Dave had no clue about what was going on between Phil and me or that I had already planned to have sex with Phil.)
Dave told Phil that they should take off my shirt and bra. I felt Phil’s hand shake as Dave said this. I think Phil was beginning to understand what was about to happen, or at least what we had planned to happen. They both pulled my shirt off and Dave removed my bra. Dave then instructed Phil to gently lick and suck on my right breast while massaging it and he would do the left. I was in heaven! I then laid down on the sofa. Phil moved to the floor and Dave laid down on the other side of me and they both continued to work on me. Phil then used his free hand to start to rub between my legs. I still had my jeans on. Several minutes later, Dave move his other hand to my crotch, but when he found Phil already there, he got a little upset and gave the signal to stop. So I sat up and said that we should stop before it got too far and that was the end of my “almost” threesome.
The next weekend, Dave went home, and Phil and I immediately started our sexual tryst for the weekend. When the moment of truth arrived, I pulled out a condom and explained what it was used for. I should have let him come in without, though, because in retrospect, I was way too cautious back then. I always used a diaphragm with spermicidal jelly around the rim plus I shot contraceptive foam into my vagina before I ever had sex with anyone and on top of that I required the guys to wear a condom. Anyway, I opened the condom and tried to put it on. It was a standard Trojan but would not easily fit around his girth. Once he understood how to put it on, he took over and was able to get it on, but it was extremely tight on him and the reservoir completely disappeared from being stretched over his head.
I was so excited to be making love to a virgin that I must have been overly wet because once he entered me, he asked if he was actually inside. Later I learned that the tightness of the condom made him completely lose sensitivity in his penis. He pumped away for awhile, but couldn’t cum because of the lack of sensitivity, so he pulled out, took off the condom, and I gave him a hand job to finish. I had three orgasms while Phil was inside me that night.
The next day, Sunday, I told Phil to get his keys and drive us to the pharmacy in town. He asked why and I told him that we needed to see if there were any condoms his size to make it better. When we got there, the pharmacist was not there because it was a Sunday, but there was a girl, probably a junior or senior in college. I asked her if they had any larger condoms than standard Trojans. Phil had no idea I was going to ask her this, he thought we’d just look around. I have never seen anyone turn as red as Phil did as we stood there discussing condom size with him there. I saw her smile and take a quick look between Phil’s legs. He turned an even darker shade when the girl asked what the problem was, if it was length or girth. I told her girth, and she pointed us to lambskin condoms. (Back then there were not as many latex options as there are today.) Phil purchased a box of Naturalambs. He had picked up a 3 pack; I took it away and gave him a 12 pack. We went back to the fraternity, and used four of the condoms that afternoon. He filled each of them quite full. Phil was so large, that I was very sore between my legs the next day.
So, to the point of my story, Phil and I had sex the following week one night when Dave was studying for a big test at the library and again all weekend the following week. Like the first weekend, I was sore the next day after each encounter. But I was so hot for Phil because of the newness of sex to him. The following week, I introduced Phil to my contraception techniques because he was curious. I showed him how I put the jelly on the diaphragm and let him watch me insert it near the closet where I kept my supplies. I then filled the foam applicator and asked Phil if he wanted to inject it. He said yes and we moved to the bed. I laid down and he inserted the syringe, but could not move the plunger. It was stuck. I assumed he was doing something wrong, so I tried, but sure enough it was stuck. Being as afraid of pregnancy as I was, I would not go with just a diaphragm and condom, so we kept trying.
After about ten minutes, Phil finally got it to loosen up and injected the foam. I told him that I really needed him inside me and to just put the condom on and come inside without a lot of foreplay. I guess all of the time it took for us to inject the foam caused my wetness and elasticity to drop below a level it had ever been because when Phil slipped inside of me, it hurt, and it hurt a lot. I’ll never forget that I looked at Phil in pain and asked him if it was possible for him to enter me half-hard. What a silly question, but it is what came out of me at my moment of agony. He asked what was wrong, and I told him that it really hurt. He started to withdrawal, but I pulled him to me and said that I felt some lubrication (which I later learned was blood) and he could try to go on. It was OK after that initial pain, but continued to hurt a little as he moved in and out.
When he finally came, he pulled out and there was blood all over his sheets and on the condom. He asked me if I had started my period, to which I replied that it takes about a month between periods. (I had my period the week before and he knew it because when we had sex, he pulled my tampon out before he licked and fingered me. I have never had any other guy want to go down on me with my period, but Phil did it all the time!) So he asked what caused the blood. I told him that I thought that he may have broken my hymen because I had never bled before as a result of having sex. I then had to explain what a hymen was to Phil and he looked at me and said that it looked like a piece of skin inside me was torn and had blood on the edges on both sides. I was sore for a couple of days, but after that, I was never sore again when I had sex with Phil.
So he was the third guy I slept with, and it was after he and I had slept together several times before I lost my hymen. I don’t know if this is common or not, but it is my weird story. This took place in 1980 when I was 18.
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