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My First True Fuckfest

Looking back, I fondly remember the weekend. While Tiffany and I didn’t work out, it was a good opportunity to learn about myself and truly experience parts of life with someone. Overall, it was the start of some very good experiences and served as my spring board for many more good experiences to come. Background I don’t remember how old I was exactly, mid-twenties or so when I lost my virginity. It is quite amazing to think about sometimes, since that is pretty late all things being considered. I learned about masturbation very early. I had a very good and loving family, if anything maybe a bit overly protective so I had the sex talk maybe a little later than some, and sure didn’t get any x-rated ideas from home, but when I had “the talk” I realized that what I had been doing for many years in private at that point was masturbating. My sex talk included a discussion that “those acts” were wrong which paired with some church and local social beliefs lead me to feel bad about what I did for some time. I was never-the-less hooked on pleasuring myself so I continued to do it. After a few years, I had come to reconcile it as part of who I was. I liked girls, and I liked them a lot. I was infatuated with many, wanted to go further with many, but in the end only pleasured myself over the thought of many. I had some friends that were girls, but never really anything more. Later in middle school, high school, and eventually college, I was extremely future goal oriented. I spent all my time literally focusing on perfecting my best outlook through hard work and study with little time for distractions or anything else. I didn’t date, the distraction was unacceptable at the time. I started my career and settled into my routine. I now seemed to have free time that could be spared for myself. I lived on my own, and was responsible. Now sexually, I wasn’t very fulfilled, but I didn’t even truly realize what I was missing. I guess by most standards, I am probably pretty average if not a bit above. I think I looked pretty good for a young American man. I was relatively trim and athletic, average height and weight, probably a bit above average intelligence, but a I had a huge amount of drive and dedication. By this point I had a pretty good job with a bit of fun money. My penis was probably average, although I have gotten some compliments from ladies since suggesting a bit more. I like to think it is a bit above average, but maybe that is just wishful. Fully erect I stand a good 6-7 inches with a good 2-3” or so of girth. I think I have an above average sex drive, which at this point I didn’t really realize. But that is something you learn along the way. At this point in my life, I pretty much have to find time to masturbate at least once a day at minimum. Only, occasionally, do I miss a day, but far more frequent than a day missed is something happening to stimulate a session where I require two or more orgasms. I am probably orgasming about 10-12 times a week. What I didn’t really think about is that I am practicing for some pretty decent stamina that I have found quite useful later in life. So living on my own; I discovered a local adult video store. I knew of porn, but between this and my personal computer not shared with anyone else now, it was like a dream come true. I guess having been sheltered a bit growing up, there was now absolutely no censorship. I was learning a lot, seeing a lot, and when I found pornography that was right for me I sure was masturbating a lot. Like any guy, I really can’t have multiple orgasms, but with the right stimulation, I could get an erection and cum again within 5 minutes after ejaculating if I got enthused enough. On occasion, I could masturbate 3-4 times in a really good 20-30 minute porn clip. Once, I even remember doing this back to back. I think after #7, I was good till morning wood the next day. So this lasted for maybe a year or so, until I began realizing that there must be something more, and there needed to be more. After all, on the porn clips that I was viewing, it sure looked like the men and women were having a lot of fun together. I didn’t want to catch a disease, I didn’t want to have a baby then but, I wanted sex. I also wanted someone special. I didn’t want to be alone. I wanted a meaningful relationship that included sex, and companionship. I was taught growing up that sex outside of marriage is wrong, but I was also taught that masturbation was wrong. Well at this point, it is clear which side of that line I was on. I did even spend some time studying sex, and believed that there was a compatibility that isn’t necessary guaranteed just because you have a man and a woman. In any regard, it was logical to me. Sex was very important to me, and I needed to be certain it worked will with my partner before we got married and I was stuck with her for life and she with me. Dating I needed to find a date, but I was not really experienced with that. I needed to find someone compatible with me, yet I worked a lot; and as far as work went that avenue seemed dry. Not only did I think it was dangerous to have a relationship at work, but the few women I worked with seemed more masculine than I, and that wasn’t particularly appealing to me. I wasn’t a partier and a drinker, quite obviously opposite as I was the dedicated future oriented scholar through school. I thought about prostitutes, however, I had fun money which would rapidly disappear to nothing with probably less gratification that I desire. Besides that was illegal, I didn’t want to deal with law issues, and it seemed like a good avenue to find some of the diseases I wasn’t looking for. I really did want a companion too, not just someone till the cash ran out. I needed sex too, God did I need it. Anyway, for the time, I could and would try internet dating. I tried an adult website for a while, however, was not gay and seemed to find either those options or people whose motives were questionable at best. Finally, I tried a more normal dating website, and after a few months and a few dates that were one and done with no connection, I met Tiffany. I met Tiffany once; it was inconvenient as we lived a fair distance apart, but we seemed to hit it off. I don’t remember the exact details but at the end of the first date, I think we talked and set up a second. Unlike virtually any date I had had at that point; things seemed right. We enjoyed our company, the date lead to a phone call, then the next date and so on. Tiffany wasn’t a perfect match, but I don’t think anyone truly is. I thought she was attractive, we got alone and we connected at a bit deeper level. We seemed to share similar values and thoughts and enjoyed our time together. Needless to say, after this date she was my new fantasy when I took care of things for myself. It wasn’t very long and I was hoping that things would go all the way. We dated a few more times typically at the end each time kissing more, petting more, grabbing a bit. We talked on the phone more, until one night maybe a month in (a bit slow, but we were moving slow due to the distance being inconvenient), I think I slipped a sexual implication in our phone conversation. I guess it was well received as we began openly talking about how our relationship was to the point that sex should be our next step. God I wanted to drop my pants and jack-off right there, but first I needed to continue the conversation and see where it lead. We eagerly set up a time for me to spend the weekend at her apartment. I want to say we both took the Friday off to extend the weekend. I would bring the contraceptives, she would cook, and get a few movies. We would try a weekend together. I remember laughing afterword. I asked her if I should come out Thursday night or Friday morning. Due to her work schedule it would be pretty late when we could first get together Thursday. She told me that it would be up to me, but she wanted to fuck sooner rather than later. I told her I didn’t want her to get the wrong impression of me but I would like that very much. We were organizing a sex date weekend; we may as well start out soon, it was clear we both wanted to. Preparations I was eager, I don’t remember how much, but it would be several days until we would meet. I know my mind wandered a lot to our weekend. She had experience with another partner, I was a virgin, we were similar age, she a bit older, we both knew these details. I remember researching a little about first times on line. From what I remember, most articles reported it as a bit of a letdown, typically, the man cums too fast, the woman doesn’t orgasm, but these articles also report it as a start of more learning and greater things to come. I purchased a 10 pack of good drugstore condoms and some spermicide lube (remembering from high school health class that this was the most practical high probability way to avoid pregnancy). I also got 2 or 3 gas station individual condoms. Looking back, I could have just got a second box, however, I was worried that Tiffany would be suspicious about the uses of any missing condoms from an un-opened box. I didn’t lie to her, nor did I want her to be suspicious. At some point, during those few days before, I practiced with the gas station condoms. I put them on and masturbated with them on. Things still felt good, and I was even pleasantly surprised they cut down on the feel some, helping to further improve my stamina. I remember late at night the night before thinking that in a day I should be either thrusting into Tiffany as we have sex or naked lying together afterward fulfilled. I don’t think I slept well. After work the next day, I tried to do a few odds and ends to keep me preoccupied. I was packed and ready to go, however, didn’t want to sit in her parking lot all afternoon waiting for her to get out of work. I was planning to arrive 10 minutes or so before her. I deliberately hadn’t masturbated that day yet; needless to say, I was wound up and eager. When my departure neared, I executed my plan. I showered and then masturbated to a profile picture of Tiffany that I liked. I came hard, and it was very good, it was also relatively quick (what I wanted to avoid regarding our first time). I then left driving to her apartment. The idea was to get rid of the immediate release, making it a bit harder to get excited, and have further releases that evening. The long drive would be enough to wind me up again anyway. I wanted better stamina, unlike the internet articles I read about. It worked, nature even stepped in to help. I arrived to her apartment parking lot about the time I intended, she wasn’t home yet, and I had a full bladder to the point it hurt. I was actually worried, I figured that I would find a gas station nearby, however, I was now there and needed to piss bad. Being a country boy, I figured I would go for a walk nearby to a wooded area. I found a secluded area and relieved my bladder. I walked back to the truck and sat patiently waiting. In a matter of minutes, I seen her car pull up and park. Oh God it finally begins. Fuckfest I grabbed my duffle bag got out and walked up to her. She had gotten out of her car, seen me and turned. We hugged and kissed, then entered her apartment. Initially there was small talk regarding the day, travels, and other pleasantries. We put our bags down and sat on the couch side by side. Initially, I was nervous as hell and didn’t know where to begin. I remember smiling and asking if we should watch TV. She laughed and said that we could but that isn’t what she had in mind. We began kissing, and petting. Tiffany was good in that she could sense my nervousness and helped. I remember she encouraged me to fondle her breasts through her shirt and rub her crotch through her pants. We were getting each other wound up. In truth I don’t think it really took all that much. Before long, she stated that she thought we should go to the bedroom and got up leading me by the hand. It was only 20 feet or so in her small apartment but we made the trip. We again kissed and caressed, and I began to help undress her. First her shirt and bra. This was the first time I was able to handle a woman’s naked breasts. They were warm and soft, as I brushed my fingers over her nipples they hardened and protruded slightly. I was excited so much so that my penis hurt in my jeans; it needed to spring free. I helped undo her pants button. She kicked off her shoes, then off with her her pants, socks, and then her panties. I realized a fantasy of mine at this point. We never talked about it, but I really like a natural hairy pussy. It was hairy with extremely minor trimming for shape. She was a gorgeous natural haired brunette. I was so turned on, this was going to be good. She was completely naked. I was running my hands over her body, exploring tits, bush, pussy, the wetness of her vagina lips. It was wonderful. Then she helped me undress. My shirt was slipped off, then she was rubbing my bare chest. My shoes, pants, and socks followed shortly after. My penis was swelling further in my underwear. I then slid them down for her too. My penis sprung forward and began rapidly finishing to its full erection. It was wonderful to no longer be inhibited by the tight constraints of my pants. She gasped a little, and whispered “Oh my”. I was worried and asked, “what” out of concern. I think her response was one that any man would like to hear. I was told that I was significantly larger than her last partner. She giggled saying that she didn’t think it would be an issue. We hugged and caressed each other’s bodies and lied down on her bed. After a few minutes, I had a good drop of precum forming at the tip as she stroked my penis; my hands could tell she was wet and ready. She asked me where the condoms were. I got up standing at the foot of the bed. I got out the box, opened it, took one out and got a little packet of spermicide. I told her what it was and even smiled when I mentioned high school health class. She got up, turned on the bedroom lamp, read the instructions, placed the packet by her bottom for a minute applying the contents to her pussy. I put a condom on in the meanwhile. She lit a large candle, turned out the lamp, and laid down on the bead stretching as she said, “Now make love to me.” She was beautiful, only minimal candle flickers accentuated her body. The light in the room was the living room light spilling in the doorway behind me. I was naked, erect, and wearing a condom. My time was now. I leaned forward and crawled on the bed between her legs. My penis was hard and swayed pointing forward to its destination as I moved closer. After a few steps of my knees, I was in position and began to lower myself on Tiffany. I had planned to tease the opening of her vagina with my penis a bit before penetrating her (an image from a porn movie I liked) however, after touching her shimmering lips first with the head for only a moment, she grasped my penis with her hand and pulled it into her. It felt so good that I continued to lean forward to her lead. It was warm, soft and my body was now on her. My weight was on her, I was in to full depth, and it felt nice. Our hair near our organs of love was pressed together; I could feel her nipples pressing into my chest. My arms were around her and we began to kiss. It felt so good I didn’t move at first, but after a few seconds I began to slide my body down and up along hers. Things were good, I remember the feeling of my pubic area around my penis being a little different than I expected. It was not bad, just different. In order to get the good angle of penetration I had, I had to bend back a little. I was gently thrusting feeling my pubic area bump into hers, however, it was nothing like the sensation of my penis sliding back and forth along the walls of her vagina. It was good, at the time I thought incredible. (It was better than I ever remember masturbation being, but later I realized a fair step below how good unprotected sex feels to me.) Initially things were a little difficult for me. I was hugging Tiffany pulling to gently thrust. This was giving me a bit of an ab workout as I really didn’t have leverage to push with my feet or pull well with my arms for that matter. Eventually, I realized that I could reach my hands above us along the mattress and grab the top of the mattress. This gave me a good grip and much better leverage to thrust by pulling with my arms. I could and did pick up the pace here a bit. I was focusing on the feels, sounds, and smells. It was terrific. Tiffany seemed to be enjoying things and I came to realize that sex actually had a bit of a smell. It was different, but I liked it, mainly since I was in positive sensory overload due to the rest of the aspects of the experience. I thought about my penis. Things were going well, and I was enjoying this very much. I had stamina, and the condom was helping me not get too excited too fast. I wanted Tiffany to orgasm, and it seemed as if things were beginning to build for her. She was holding on tight to me moving her bottom to meet my thrusts. We looked into each other’s eyes though the dim light. It was hard to see all, but I was pretty sure that I saw the intense look of desire that I am sure I had looking back from me. Suddenly, she began to cry out and pulled me close. I didn’t think her hold could get much tighter. It was hard for me to keep thrusting, yet I did a little, her vagina held tight and maybe even quivered a little around my sliding penis. As I felt her grip lessen, I asked her if she came. She was out of breath a little when she said that she did. I kept thrusting thinking that I was a bit surprised she came so soon. It was a good thing, and she still seemed to be enjoying things as we continued. Our bodies had generated some lubrication making my penis slide a bit easier, occasionally a sticky slurp or smack was now audible. Tiffany had cum; things felt great, but I decided it was my turn. This was further emphasized by Tiffany coaching me saying she wanted me to come. I began thrusting harder, the bed was now making a thumping noise in time with our thrusting and she was beginning to hold on tight internally and externally. The sounds, her response, the feeling, and the situation; I was more turned on than I had ever been in my life up until that point. My orgasm was building, things felt great. I began to lose track of the other sensations around us. It was just the feel of my penis I could focus on, as the wonderful pleasure built and intensified. I was almost there, when I felt her tighten and scream again. As I felt the distinct tightening of her vagina; this was too much for me. The feeling intensified to its maximum pleasure, and I began my first orgasm. Involuntarily, my muscles tightened, and I slammed my penis as hard and deep forward into her as I could. It was wonderful. Despite my masturbation earlier that night, the ejaculation contractions were long, pleasurable, and intense. I don’t know how many contractions I felt, but they were good and intense and drove my feelings in waves of pleasure as I held my penis as deep inside of her body as I could. Slowly afterward our grips released on eachother, and we stopped clinging tightly to eachother. I could feel the cum around the tip of my penis. It had inflated the condom, and it was now seeping past the head to the shaft. We kissed and I gently pulled out. As the head of my penis slid out the feeling was intense even with the cum inflated condom, so I laid on my back next to Tiffany. I said, “Wow I thought that was good.” She asked me if it was really my first time several times as we talked. I assured her that it was, even though I got the impression that she had some doubt. I told her that I masturbated some which evidentially helped my stamina. We talked a little and I got up and went to the bathroom. I took the condom off and threw it in the tub (figured sperm seeping into a wicker trash can wouldn’t be good, and I could deal with it later.) I wiped off my penis, and went back to lay with Tiffany. As we laid there, we talked about movies she got and plans for meals briefly. We then talked about sleeping preferences, agreeing to sleep together. I told her that I normally sleep naked, only when away or seeking modesty due to guests would even consider wearing plain underwear. If it was all right with her, I planned to sleep naked. I no longer had anything she hadn’t seen. She laughed saying that that was alright. She would wear a shirt due to comfort and habit, but would probably be trying to get used to my way, as it could more easily provide for play during the night. I told her I was game, hopefully tonight and she laughed. Saying maybe we should now sleep since our night sleep would probably be interrupted. I agreed, but then I told her I wouldn’t even mind having sex again before we try and sleep. I know this caught her off guard; but it had probably been a good 20 minutes or so, I was beginning to regain an erection due to our current talk. I was wound up, things were going well, and I was definitely interested. She sat partially up turning my way exclaiming “Now, we just finished.” She looked down along my body to my stiffening penis and smiled a devilish grin saying “You’re serious.” I smiled saying sometimes I get wound up and can go again somewhat soon. As I remember fishing out the second condom and putting it on, she said that she thinks the jelly stuff was still good. I agreed, and thought that this is going to be a good weekend. I have to be in the right mood to cum several times in a row. I was that night. I only had one more orgasm before sleep. I don’t remember it as well as the first, however, knowing myself, I know it was intense. I have noticed that as I cum in succession and run out of sperm, my stamina goes up, the orgasm is more intense, and the contractions associated with sperm ejaculation are much more intense and pleasurable despite the fact that I emit much less sperm. Tiffany came that time again probably more than once. The weekend was good. We spent time together, she cooked, we watched a few movies, and most importantly we fucked. We tried different positions, we woke in the middle of the night, and for the most part did little else. I think one day we went to a craft thing she was interested in seeing briefly, that was primarily justified since we needed to pair it with a condom run. Overall, I think my balls got drained; we both enjoyed our presence, and we learned about each other. Final Thoughts One of my most valuable lessons happened mid-day Friday I think when we were vigorously thrusting during sex. I don’t know exactly when, but suddenly things seemed incredibly good, I orgasmed shortly thereafter and pulled out only to find the condom had broken. I guess that is why health class recommended the spermicide too. Fortunately, we had fucked enough that I had little sperm to ejaculate, with the spermicide, nothing happened, but I got an appreciation for how much better unprotected sex feels. That opened me up to a whole new realm of stories perhaps for a later time. So in any regard, things didn’t work out for Tiffany and I, but I think the experience was good and we got to learn a lot about each other and ourselves. Sex is a powerful and wonderful teacher, and I look forward to further good things to come. I don’t regret it, and will always have a special place in my memory for that weekend of my first time.

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