Lost My Virginity To An Older Man

I was a nineteen year old college student attending the University of California - Berkeley when I lost my virginity to a forty-three year old man. I first met Randy at a bookstore where I was browsing the books. We bumped into each other in the travel section and he struck up a conversation with me. I knew that he was much older than me but he was also good looking and had a wonderful manner about him. After about ten-minutes he invited me out for a coffee which I accepted immediately. At the coffee shop Randy kept me spellbound with his talk of travel and his views on life. He knew exactly what to say to get me interested in him so I was hooked when he suddenly asked me out on a date. I quickly agreed and we arranged to meet at the bookshop where we met, the next day. I met Randy the next day for lunch as planned and he once again swept me off my feet with his charm. We talked for hours before he invited me to window shop at the various shops in Berkeley. For those who don’t know the area, Berkeley California is a “hippie” college town with lots of wonderful, small stores that sell very one of a kind items. The people living in the city are also unique and all of it put together gives it a feeling of almost being in a foreign country. As we walked past the stores Randy suddenly took my hand and I almost swooned at this simple gesture. We continued walking hand in hand and I listened with awe as Randy pointed out various things or made some wonderful comment. When we finally stopped in front of a large house that was sub-divided into small apartment, Randy told me that this was where he lived and asked if I wanted to come in so I could relax a bit and perhaps have a snack. Who could resist that? Be still my soul! I agreed and went into Randy’s home where he asked me to take my shoes off. He said he liked the Asian rule of no shoes in the house and I quickly complied slipping off my shoes at the door. He had wood flooring which actually felt good on my bare feet and he invited me to have a seat on his couch while he prepared our snack. Randy commented on my feet telling me they looked very pretty. I was glad that I had taken the time to get a pedicure a day earlier as I had no idea that Randy would be so interested in my feet. At the time I didn’t realize it but Randy had a huge foot fetish which I didn’t understand at the time. To compliment my feet was as if you complimented my hair style. What’s the difference? I didn’t realize how sexualized feet actually were. As far as Randy’s home, it was a typical bachelor’s pad that was a bit cluttered but not too messy. I looked around for those exotic items Randy had talked about but he said that they were being stored and he would have to show me another time. As we talked Randy kept touching me in non-sexual ways until finally his hand came to rest on my foot. Since I didn’t realize Randy’s obsession with feet, I didn’t think anything of it. Once Randy saw that I didn’t protest or try to remove his hand from my foot he began to rub them. It actually felt wonderful after all the walking that we had done that day and soon he put both of my feet into his lap where he continued with the massage. I felt like a pampered princess. I suppose the point I realized that something was going to happen was after about fifteen minutes of massaging when I noticed that his hands were going higher and higher up my legs to the point that he even went underneath my skirt. When I felt him brush against my panties I knew something was up. It took a few more minutes but it finally dawned on me that Randy was attempting to seduce me. Did I want to go through with this? I could leave now and nothing would probably be said. However, I wanted to go to bed with Randy, I really did. Was that such a terrible things? I had no religious scruples and had avoided sex for no good reason other than I was waiting for the right guy. Others enjoyed sex without attachments, why couldn’t I? I looked at Randy as he continued rubbing my feet and smiled. So this would be the man who would take my virginity away. I couldn’t wait. Randy must have read my mind for almost as soon as I made my decision to stay Randy leaned in and kissed me gently on the lips. It was quite unexpected but it felt nice at the same time. Randy was encouraged when I didn’t protest and soon the kissing became quite intense. Randy’s hands began moving along my body and I was beginning to feel excited and almost intoxicated at my present situation. As our make out session continued, Randy slowly positioned me on the couch and before I knew it he was on top of me essentially dry humping me in the missionary position. Though we were still fully clothed it felt so intimate to have Randy so close to me and I decided that I wanted Randy to make love to me. However, I was deeply embarrassed when I felt his very erect penis underneath his pants as he rubbed against my groin area. I didn’t know what to do or say so I just kept quiet and ignored it. Randy seemed very encouraged during our kissing session as I was making moaning noises of enjoyment. This must have encouraged him because he suddenly stopped at one point and gazed lovingly (actually it was lustfully) into my eyes before he sat me up, unbuttoned my blouse, and unhooked my bra all while kissing my neck. His lips on my neck felt so good that I didn’t even think to protest and in just a few short moments Randy’s hands were caressing my breasts. Shortly after that he pulled off my blouse completely off and I found myself nude from the waist up. I was strangely calm and I felt like this was all so unreal and that I’d wake up any moment. After Randy took off my blouse he placed me back into position on the couch and we continued our intense kissing but this time he also was kissing and fondling my breasts as well. I soon began experiences a new sensation of pleasure that I’d never felt before and I wanted more. If this was what sex was like then maybe everything was going to be all right after all. I felt a twinge of pain as one of his fingers began entering me and I told him that it hurt. Randy immediately pulled out but continued rubbing between my legs and I began to feel an extremely pleasurable sensation radiating from deep within me. Randy suddenly stopped and asked me if I was on any kind of birth control. I happened to be taking birth control pills for a women’s health issue. It was funny at the time since I wasn’t sexually active but now it seemed like it had been a prudent thing to do. I told him that I was and I saw a big smile come across his face. I also told him that I was a virgin and Randy told me the famous words all men tell young girls they are about to deflower, “Don’t worry,” he said, “I’ll be gentle.” Randy then stood me up, took my arms, and pulled me close to him. I still had on my skirt but I was nude at the top. Randy gave me a hug before guiding me into his bedroom which was just a small room near the main doorway. Randy sat on the bed and pulled me in front of him and took my skirt and panties off in one fell swoop. I was now standing completely naked before this man who would soon be joining his body with mine. He directed me to the bed and had me sit down on the edge while he took off his clothing. I was taken back when I got my first glimpse of his penis. Though today I’d say it was very average in length but perhaps just a bit thicker than the normal male, it still looked like a monster to me. I wondered how I was going to get that thing inside of my body? Randy told me to trust him and that he would teach me all about sex. My lesson started when Randy guided me towards his waiting penis. He placed only the head of his penis into my mouth and told me to suck as hard as I could and move my hand up and down the shaft. I did as instructed and started sucking and moving my hand. It was a weird feeling having a man’s penis in my mouth but Randy seemed to be enjoying it and it made me happy that I was the one giving him this pleasure. When Randy suddenly pulled himself out of my mouth I was concerned that I’d done something wrong. When I asked him if I was doing it right he told me that I had done a great job but he didn’t want to come too quickly because it was now time for the fireworks. With that I assumed he meant intercourse and I nervously got onto my back in the bed and prepared for whatever came next. Randy laid down beside me and kissed me gently on the lips as he parted my legs. Before long I felt his fingers massaging the lips of my vagina and it felt wonderful! Up until now I hadn’t even masturbated and had no idea what an orgasm should even feel like. Was I having one now? I didn’t know but it sure felt good. As Randy continued massaging my vaginal lips it seemed that he was searching for something with his fingers. I didn’t know what it was he was looking for but his finger finally stopped at a certain point near my opening and when he started rubbing that spot a sudden small wave of pleasure swept through my body and it took my breath away ( it turns out that it was my clitoris). As Randy’s hand continued moving between my legs the pleasure was growing and growing. Maybe my years of unintended celibacy actually paid off for me since it didn’t take me very long to suddenly explode in a huge burst of pleasure so intense that I almost fainted. I was actually propelled to a different level of consciousness as the waves of pleasure swept through my body. I don’t know how long it lasted but when I finally recovered enough to open my eyes Randy was near my face smiling. If Randy could do this with his hand then what pleasures awaited me when he entered my body? I almost couldn’t wait. It took me a few moments to recover but during that time Randy had gotten up, opened his night stand drawer, and took out a bottle of what looked like oil. He stood near me and I watched him put some of this oil liberally onto his hand before rubbing it onto his penis. Randy placed the bottle back onto the table, returned to bed, took one his hands, and spread open my legs widely. The moment of truth had arrived as I was about to have sex for the first time. Randy mounted me and I adjusted my body for him by spreading my legs out a bit further. A few moments later I felt him place the tip of his penis at my entrance and waited for the ecstasy that was sure to come. As Randy’s penis began stretching my vagina opening I felt pain. Randy saw that I looked distressed and stopped to reassure me that everything was all right. He kissed me and held me in his arms and waited until I got used to him. The pain slowly subsided and I told Randy that I was feeling fine. I reached down between my legs and felt Randy’s penis to make sure that he was inside of me. He was and I felt relieved that my body was able to accommodate his manhood. I waited for the sex to begin. Randy began to make very shallow thrusts and though there was still some discomfort it didn’t hurt as much this time. As things got smoother Randy began moving quicker and deeper inside of me and before I knew it I realized that I was actually having sex. Though I didn’t have the feelings I did when I had my first orgasm with Randy’s hand, I did enjoy the feeling of Randy moving inside of me. I felt like a real woman now and all that was left was for him to orgasm inside of me to complete the act. I was in no rush though as I wrapped my legs around Randy’s waist and held onto his back. Actual penetrating sex probably lasted about five minutes and we stayed in the missionary position the entire time. Soon I felt his thrusting getting faster and deeper when unexpectedly I heard Randy give a sharp moan that startled me for a moment before I realized that he must be having an orgasm. I felt his penis pulsating inside of me as I held on to him tightly as I realized that this must be the point where Randy was making his release of sperm inside of me. Though I didn’t orgasm, or even come close to any actual sexual pleasure during intercourse, I still enjoyed the intercourse and everything leading up to it immensely (except for the initial pain). Plus I had Randy’s sperm inside of me now. I was a woman at last. Randy stayed unmoving inside of me for a few moments before pulling out and we laid there together on the bed with Randy’s hand lying on my belly. I covered his hand with mine and held it there to keep our closeness alive. I listened to Randy’s heavy breathing and it sounded like he had just run a marathon. After about five minutes I began feeling something dribbling out of my vagina which worried me because I thought that perhaps my period had started early brought on by Randy’s penetration of me. I quickly wiped my fingers between my legs and looked at them. There was some blood on my fingers it wasn’t enough to be blood from my menstrual cycle. There was also another thicker, clearer substance that I didn’t know what it was. I decided to be bold once again and asked Randy about this and he said that this was his sperm coming out of my body and that it was completely normal. After about a half an hour we got up and I took a shower and was amazed at the gobs and gobs of sperm that was leaking out of my body. I had to use my emergency tampon to plug myself up to keep from leaking on the way home. That was the story of the first time I had sex. I stayed with Randy for about two months we continued having sex even though I realized early on that Randy wasn’t going to be a long term man for me. After the initial girlhood crush on him I saw some qualities that I didn’t like (nothing really bad) and I knew I could do better. However, he had me hooked on sex and I was eager to learn even though he wasn’t a particularly good lover (as I found out later in comparison). Randy did show me the basics of sex and gave me the opportunity to practice on him. I learned to give him very good oral and to even swallow his sperm afterwards, something that I do to this day. Unfortunately, he never reciprocated and I had to get my first oral experience from my next boyfriend. Intercourse never lasted long enough to achieve an orgasm for myself though I did enjoy the feeling of Randy being inside of me for those short moments and I loved being filled up with his semen. I took to carrying more tampons in my purse in anticipation of the large amount of sperm that stayed in my body throughout the day after having sex. My one and only orgasm with Randy inside of me occurred towards the end of our relationship when for some reason Randy was unable to have an orgasm and he flopped on his back frustrated. I don’t know why but I climbed on top of him and tried to reassure him. I felt his penis behind me and it was still very hard so without thinking I reached back, took a hold of him, and slipped it inside of me. Randy didn’t move so I started moving and found that when I varied the speed and depth I could get the penis to hit and rub certain areas that felt good. I experimented with this and soon I was feeling an orgasm building up within me. Randy was watching me in fascination and I suppose this excited him for I felt his penis get even harder inside of me. I closed my eyes and just gyrated my hips with his hips and concentrated on my pleasure. I began moving faster and faster up and down Randy’s penis until I abruptly exploded in orgasmic pleasure. I couldn’t believe it but I had used a man’s penis to give myself an orgasm. It was wonderful! The waves of pleasure lasted for a long time and when it was finally over I collapsed on Randy’s chest totally exhausted. Randy let me rest for a moment before maneuvering me back into the missionary position where he quickly entered me with gusto. He moved deep and fast and it actually was feeling good. I suppose I was still in the afterglow of the orgasm and Randy’s movement inside of me just made things better. He lasted only about a minute before he flooded me with his sperm and I remember making a little moaning sound not because it felt particularly good but because I enjoyed the feeling of being filled with sperm. Unfortunately, everything came crashing down that next weekend. We had gone out for lunch and had returned to Randy’s apartment where I was going to spend the night with him. Randy decided he wanted to have sex early so we could watch a late night move. We went to bed and began having sex. Randy had just entered me when I thought I heard the front door being opened. The bed was positioned in a way that you couldn’t see the doorway and since Randy was preoccupied he didn’t seem to notice the sound. Since Randy lived alone and had told me that he had never married I thought that it was just an outside noise and decided not to pay much attention to it. I returned my concentration to Randy’s deep thrusting penis and was just wrapping my legs around his waist hoping I would be able to have a repeat performance and the previous time we had sex when suddenly I heard a female voice shouting, “You bastard!” In shock Randy stopped and turned his head and I saw his eyes go wild as he shouted, “Veronica!” Randy quickly pulled out of me and started putting his clothing on. I was absolutely shocked at the sight and didn’t know what was going on as Veronica began shouting at Randy and slapped him in the face yelling, “You said you changed! You’ve shamed me and the children!” She stormed out of the apartment. I turned to a stunned Randy and asked him what was going on and Randy but he didn’t answer me. Instead he got dressed and went outside after Veronica. I didn’t know what to do so I got dressed and waited until he got back. By then my wits had returned and I asked him if Veronica was his wife. He sheepishly admitted that she was and I told him that he had lied to me about being married and ran out of the apartment. As I was walking down the sidewalk a car pulled up beside me and I saw Veronica with three children sitting in her car. She had been crying. Veronica cursed me and told me to stay away from her husband. I tried defending myself telling her that I didn’t know Randy was married. Between sobs Veronica told me that Randy had a previous affair with another young college student and that she had caught them in bed as she did today. She said that they had separated but had only recently decided to get back together since Randy had sworn that he was a changed man. I looked at the children in the car and was overwhelmed with grief. They looked so innocent and bewildered that I burst into tears. I watched Veronica drive off and I stood there sobbing. Randy came out and tried to talk me back into his home but I ran away and then walked for hours before finally arriving home. I then took a long shower and then sat there on my bed horrified at what I’d done. Though Randy would later call me and admitted that what Veronica had said was true he said that he loved me and wanted to be with me only I hung up on him. Natalie