tagFirst TimeLost Virginity and Boy Did It Hurt

Lost Virginity and Boy Did It Hurt

byNatalie3442©

My name is Natalie and this is the story of how I lost my virginity. I can best describe it as great pleasure followed by great pain. I was a virgin up until my second year in college when I had just turned 20. I hadn't even dated much, and when I did go out it was more of a platonic type date rather than something hot and heavy. I preferred to spend my time reading and studying rather than going out with guys.

I was a real virgin who knew nothing about sex. Oh sure, I took biology courses and had the knowledge and the mechanics of sex in my head. I knew how sex was performed by two people and knew where babies came from, but beyond that I was clueless.

I've had such a high sex drive for most of my adult life that the idea that there was a time where I could be uninterested in sex seems almost strange to me. I didn't even masturbate; having no idea that one could give oneself sexual pleasure (to tell truth, I still don't preferring sex to self-pleasure). When I was with my girlfriends, they would talk about "boys" and the dates they went on but it really didn't interest me. I knew that one day it would happen and I would take the plunge into womanhood, but not today.

It's not that I grew up in a prudish family who didn't believe in sex. My parents were very open with my siblings and myself and didn't impose any Victorian values on us. We were free to explore as we saw fit as long as we knew the dangers out there. I just happen to not take much notice to sex the first part of my life.

So here I was in college having just turned 20 and with no sexual experience under my belt. One fact you need to know: I was on birth control. My doctor had placed me on them to help in some issues during my periods. They did help and I took them religiously just as I would a vitamin supplement. It also saved me from getting pregnant from my very first lover Hans, but I'm getting ahead of myself.

I met Hans in the library. He was quite charming and good looking (very good looking as a matter of fact) and he invited me out to the campus hangout for coffee. I told him that I would only after I get my homework completed, and he agreed and worked on his own assignment while waiting for me.

About an hour later we were on our way for our "date" at the coffee bar. We had a good chat and I found out that he was from Florida and was majoring in sports injuries, or something to that affect. At 29, he was a senior having just gotten out of the military and was going back to school using his government benefits. I have to admit that I was intrigued with the idea of an older, more experienced man interested in me. When he asked me out for a proper date the next weekend I accepted immediately.

When I got home my head was swimming. I was very taken back at how handsome he was and then the self-doubt came in. I didn't consider myself very good looking and wondered why he was interested in me. I decided to just go for it and have a good time. I then put it out of my mind and spent the next few days until my date studying.

Friday night came (the beginning of a three day weekend) and I actually grew excited. Hans came to my home (an apartment I shared with two other girls) and picked me up and we walked to our dinner destination. Afterwards, we went to a movie and then he took me home, holding my hand as we walked. It was so romantic.

He got me safely to my home and gave me a peck on the cheek and asked me if he could take me out the following day. I immediately agreed and Hans departed while I went into the apartment. As I lay there bed I thought about Hans and I actually began to think what it would be like to be held in his arms. The first stirrings of my future sexual self was starting to come out.

The next day Hans picked me up and we went to the nearest BART station (the subway system for the San Francisco Bay area) and took it across the bay to San Francisco. We then found our way to Fisherman's Wharf where he took me on a trip to Alcatraz Island (the old prison island) for some sightseeing. It was my first time there. When we came back ashore we went out to a very nice seafood restaurant and had a wonderful conversation. We really hit it off and I felt like we had a wonderful time talking, walking, and just being together.

I still couldn't believe that such a handsome, older man was attracted to me. This second date definitely began to stir up my deep, inner, sexual feelings that I didn't know even existed within me (later I realized that it was pure lust). He got me back home safely but this time we kissed. It wasn't my first kiss but it sure was the best one I'd ever received up to that point.

We made arrangements to go out again the next day (Sunday) in the afternoon. I had to study in the morning and even though I wanted to spend the entire day with him, my head was screwed on tightly enough for me to realize that I needed to study before any personal pleasure. I told Hans that I needed to do some school work first and understood and he said that we would pick me up in the afternoon and we would take it easy and relax.

When Hans picked me up the next afternoon we first went out to get something to eat and then we walked around dong some window shopping. As it got to be about 5 p.m. he invited me to his apartment that was not too far away from where I lived. I felt safe with him so I accepted and off we went, hand in hand, to his home.

When we arrived I found that he lived in a one room apartment which was part of a duplex. It was near Shattuck Avenue (for those from Berkeley) but with lots of shrubbery and flowers all around the various homes, it seemed to block off the traffic noises. He invited me inside and when I entered I found that he kept a neat bachelor's pad and made me feel at home. I almost expected for him to change into a "sex demon" and attack me on the spot. I don't know why, but this was the first time I'd ever been in a single man's home, and I really didn't know what to expect.

He made us a little snack and we relaxed on his couch watching television. He then did something that I mark as my very first sexual experience: He put my feet onto his lap, slipped off my sandals, and started to give me a foot rub. I'd never had one before. It was so sensual and felt absolutely wonderful. Sure, I've given myself ones when my feet were sore, but never has a man taken my feet and rubbed them, and I'm here to tell you that I thoroughly enjoyed it. Give me a foot massage today and I'm all yours.

We talked as he massaged my feet. I didn't know if he had any ulterior motives, I just know that I enjoyed that handsome man rubbing my feet and toes.

As we talked his hands were getting higher and higher on my legs. I was wearing a long dress and I soon noticed his hands were up past my knees. It was feeling quite good so I didn't protest. To tell you the truth, I liked what he was doing and was even getting a bit excited. As his hands reached higher I felt him move toward my inner thigh and I suddenly got a very pleasant feeling between my legs that I'd never felt before.

Today I know that this feeling was me getting aroused, but at the time I'd never been stirred or sexually stimulated in any sense of the word. Remember, sex was an academic exercise for me. If I had to take a written test I dare say I'd probably have gotten a grade in the high 90s, but would have failed the practical exercise.

At this point we didn't talk anymore as he carried on his task of rubbing my inner legs. He did ask me if what he was doing was all right and I told him that it was. He continued to do what he was doing and my arousal level rose even more. He then asked me a very personal and intimate question which sort of shocked but got me excited at the same time. He asked me if I enjoyed my breasts being rubbed. I was taken back at his boldness and was too shy to answer. I blushed and he told me he was sorry for asking and continued rubbing my feet.

I regained my composure and told him that I wouldn't mind having my breasts rubbed if it felt good. That's all it took and Hans immediately put one of his hands onto the side of my chest and slowly headed for my breast. This was the time I could have said no and turned back and everything would be all right. Nothing vital had been touched and no lines had been crossed. I knew that my reaction would set the tone for the entire evening.

As his hand began to brush against my breast I felt another twinge of pleasure and a rush of excitement came over me. His hand then made full contact with my breast and I discovered that I liked it very much.

I still remember the pleasure of having a man's hands touching my breast while his other hand was underneath my skirt still rubbing my legs. The double pleasure that Hans was giving me was almost overwhelming. It then dawned on me: I was going to have sex very soon. If I was going to back out now would be the time. I thought about it and wondered if I should let things just go as they were and see what happened. My new found arousal made the decision for me and I just decided to go with the flow.

My dress showed off some cleavage and allowed for easy access to my bare skin. Hans's hand had found this spot and was touching my bare skin but was also slowly going underneath my dress. Not wearing a bra, Hans's hand had no barrier to slow it down and he was soon making full contact with my naked breast. The pleasure that hit me surprised me. I don't remember making any noises except that I did let out a "sigh" sound. He then kissed me and I kissed him back.

As we kissed my head went lower and lower onto the couch until I was lying down on my back and Hans was on top of me. He had taken his hand out of my lower dress and started touching me all over my body. I found that I loved his kissing and touching. I let my hands explore his body but made sure not to touch his "vital" areas. He then stopped, held my face in his hand, and looked at me for a few moments before telling me that he wanted to make love to me. It sounded all so terribly romantic and almost like it was out of a book. I told him that I'd never been with anyone before and asked him if he was sure that we should do this.

He assured me that it would be all right and I kissed him which he took (correctly) that I wanted to proceed. We continued kissing and touching for probably ten minutes or so before he stopped, stood up, and held out his hand. I took hold of him and he pulled me up and escorted me to his bedroom. It was dark by now so he turned on a little lamp that had a low wattage bulb which gave us just enough light to see each other. I was actually grateful for this light because I was feeling terribly shy about Hans seeing me naked and didn't want the full exposure of a well lit room to make him take one good look at me and run away.

I actually laugh when I think of this today. My photographs of myself during that time show a young lady who had a great looking body. I wish I could have that same body today; however, the men who see my 50-year old bodies today don't complain and seemed turned on by what they see. I really didn't have anything to fear and know today that Hans was probably very stimulated to see my naked 20-year old body ready to receive his body.

Hans disrobed me slowly until I stood there in just my panties. I felt very embarrassed but Hans reassured me that I looked beautiful and he then took of his clothing off and I didn't feel so self-conscious after that. But I was afraid to look down at his penis, so I kept eye contact with him. I don't know why I didn't want to look at his unseen manhood since, very soon, it was going to be inside me. I suppose it was the terror I was feeling mixed with this new feeling of sexual arousal.

He took me into his arms and I felt the bulge of his penis push against my stomach. At first I was shocked and almost pulled back, but I calmed myself and soon got used to the feeling of a naked penis actually touching my bare skin.

Hans began to kiss me and I felt his hands go to my panties and begin to slide them off of me. I helped him and soon I was also completely naked before him. We sat down on the bed and kissed for a few minutes before he got me onto my back where he could have full access to my entire front area. I then looked down and for the first time I caught a glimpse of an adult's penis for the first time.

It looked big and mean and immediately began to have doubts on whether or not I would be able to get that thing inside of me. I again laugh at myself at how naive I was at the time. I suppose for a girl that had never seen a real adult penis up close then the first one would seem like a monster to anyone. Today, I'd describe it as quite average looking. It was circumcised and probably no more than six-inches long (I believe a little under six inches is the normal size for adult males -- don't believe all the hype about sizes) and I was able to put my fingers around it.

I'm actually thankful that he was of normal size and not someone that was larger or thicker. This was bad enough that I was going to have that inside of me, make it any bigger and I'd probably have run away in terror.

Hans and I continued to kiss, touch, and cuddle each other on the bed. When he began to kiss and suck my breasts, the feeling of pleasure started to return to me as my shyness fled. This pleasure of Hans sucking my breasts was so new to me, so intense, that I wondered if I was having an orgasm as described in various books I've read. I turned out not to be the case but it sure did feel good. I was actually beginning to yearn for intercourse because if Hans sucking my breasts felt this good, I reasoned that a penis inside of me could only send me to heaven.

He then stopped sucking my breast and started to move down my body, kissing as he went. The pleasure wasn't as intense, but it still felt good. However, he began to get nearer and nearer to my vagina, and I had no idea what he was going to do once he reached it. Slowly I felt him getting lower and lower as he took his time kissing and sucking me.

When he arrived at my vagina hair line I almost stopped breathing in anticipation. "What was he going to do?" I thought. I didn't have to wait long as I felt the first lick of his tongue between my legs.

I almost couldn't stand it. I was being licked by a man on my most private of areas and it had sent a bolt of pleasure through my entire body. I didn't know what he was doing but I wanted more. He soon began to lick, kiss, and suck me between the legs and for the first time I began to actually lose myself in what he was doing. Hans was licking a far more sensitive area than my breasts and I was almost beginning to pant. Hans continued licking and kissing the area and when he began to focus on one spot in particular (the clitoris) I almost couldn't contain myself.

I didn't know what was happening to me as feelings of something good began building up within me. It was like a great pressure of something building up somewhere in my body. I can only compare it to a wave that was approaching and getting bigger as it got nearer. Hans must have known by my body's reaction that I was getting near an orgasm and he continued to do his thing to my clitoris. Then the wave of my very first orgasm hit me.

I can see why the French call the orgasm "La Petite Mort" or "little death." I could have been dying at that moment and wouldn't have cared one bit. I was in a totally different world as this pleasure swept over me. I don't remember if I made any sex noises (I probably did) but as the wave of pleasure was sweeping over me I felt pure ecstasy. I had my eyes closed tightly and could see spots of white flashing within my head. As the pleasure wave slowly subsided and went away I was totally exhausted and spent. My brain felt like electricity was fluttering around inside and I couldn't talk. I don't even remember what Hans was doing, if anything. He probably was sitting back watching me in wonderment.

When I had recovered enough he asked me if I was all right and I smiled as I told him that I was fine. He hovered over me and began rubbing my breasts, but after my first orgasm the small pleasure of having my breast touched hardly even register. It was like eating an orange after finishing a bag of candy. No matter how sweet the orange is you aren't going to taste it after the candy.

Hans then asked me if I was on any birth control. I told him I wasn't, even though I was taking birth control pills for a medical issue, but didn't connect it to actual birth control. He asked me when I was due for my period and I had to sit and think and I realized that I didn't know at the moment (the orgasm had really scrambled my brain) but took a stab at it and gave him a date. He did some figuring and told me that I was safe and proceeded to part my legs and mount me.

Today, I'd never allow a man to enter me with such flimsy calculations, but I was young and stupid and thank God I actually was on birth control. I didn't argue with him and wondered if actual sex would be any better than what I just had. I was excited to find out. Hans took some lubricant from his night stand drawer and spread it around his penis and then put a few squirts between my legs before getting into position. I was on my back with Hans on top of me between my legs. I could feel his penis poking around my entrance but not able to get in. Hans had to pull back, take hold of his penis, and place it at my entrance. He repositioned himself on top of me and I felt his penis trying to push inside of me.

He managed to get his tip inside of me before I screamed in pain. It hurt like hell and it surprised me. It wasn't supposed to hurt, was it? Hans pulled back out and apologized and put some more lubricant onto his penis and a more generous helping at my entrance and tried again. The pain came back as he began to push again. As I felt him go in a bit deeper I felt a tearing sensation between my legs, and I was suddenly fearful for my health and safety.

Hans assured me that it was all right, that he was just breaking through my hymen. I had heard of that and knew that it did indeed have to be broken and could cause some pain and bleeding. Only because of this did I let Hans proceed. I also didn't want to leave his apartment still a virgin. If I went this far I needed to complete it. The pain continued as Hans pushed in deeper and I had to really control myself from crying out in pain. Finally Hans stopped and remained motionless. He told me that he had pushed in as far as he could go and asked how I felt. I told him that it still hurt but the pain was subsiding and asked him not to move for a little while. Hans remained motionless above me until the pain was pretty much gone.

When he felt me relax he started moving a little bit and the pain came back, but not as intense. The more he moved the lesser the pain until he was able to move freely inside of me without much discomfort. I had done it! I was no longer a virgin. A man was inside of me and I was obviously giving him pleasure if the noise Hans was making was any indication that he was feeling good.

He lasted for maybe five-minutes when he told me that he was coming. I didn't really understand what he meant by "coming" but when I heard him grunting and giving me shallow thrusts instead of the longer, deeper ones, I knew something was up. His thrusting slowed until he had fully stopped and I heard his heavy panting near my ear.

He pulled out of me and collapsed onto his back next to me. He apologized that he had caused me pain but hoped that I had enjoyed my first time. I had to be honest with myself that even though the pleasure of my orgasm was very intense, the pain from intercourse seemed to cancel all that out.

I didn't tell Hans this but instead that it had been wonderful for me which seemed to make him happy. Suddenly I realized that I was oozing out a liquid from between my legs. I excused myself and went to the bathroom and saw what I could only describe as an "ooze" was dribbling out of me. I then put two and two together and realized that this was Hans's sperm.

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byNatalie3442© 4 comments/ 39822 views/ 3 favorites

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