Lost Virginity and Boy Did It Hurt

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.