My sister was my very first virgin and now I was going to get her daughter’s virginity too.
I love it when young girls about ten or eleven start to develop their breasts. They are kind of pointed and cute to see in their T-shirts. They are even kind of proud of them.
I love it when a young lady about twelve or thirteen starts to get that thinner waist, growing toward that hourglass figure that men love to admire.
I really love it when a young woman about fourteen or fifteen starts thinking about sex and loosing her virginity. I absolutely love to de-flower virgins, to be the very first man to invade their inner most depths. This is a man that they will never ever forget as long as they shall live. Men will come and go throughout their lives but the one they will always remember is the one they first give themselves too.
I may be a pervert but I try to see to it that each and every girl feels special.
It all started when my sister Jean and I were young. I am a year older than Jean is. When she was fourteen I started to notice her body changing and I took every opportunity to compliment her on her good looks and to touch her sexually. I would pat her ass or brush my arm against her breast whenever possible. Then when I was sixteen she started to get curious about sex so I helped her out all I could. Whenever Jean asked me a sexual question I would ask other people or look things up in the library to find her answers. Naturally when she asked to see my cock I showed it to her without hesitation. That day we were home alone so I stripped naked and let Jean look and touch me all she wanted too. I let her hold my cock while I pissed and let her aim it, I let her get it hard as if that took any effort, and then I even showed her how to jerk me off. She loved it especially since I had not asked her to do anything in exchange. It was strictly one sided.
The very next week I did it for her once again but this time Jean had invited three of her girlfriends over to look at me naked too and to touch me all that they wanted to. Again I did so without getting anything in exchange.
Then the weekend after that all three girls came to our house for a sleepover. I was the only boy there so they included me in everything. I got to slow dance with each of them and watch them slow dance with each other too. They pressed their budding breasts into my chest. I got to play spin the bottle where the four of them sat in a circle and spun the bottle while I just got to kiss the winner. I was the winner each and every time. As I kissed each girl I got to feel her tits and no one objected not even my sister. I even started slipping my hand up under their shirts and they let me. The next time we slow danced I got to feel of their pussies through their panties and their asses while they each got to feel me up.
After dinner the girls changed into their pajamas. Yes, it was a pajama party. Jean even handed me a pair of her pajamas to wear so I put them on. She told me that the girls were not going to wear anything underneath their pajamas, no bras, no panties, no nothing and that I was not to wear anything under mine either. No problem! Except that my cock was not confined very well. The girls looked totally covered but the ultra thin material sure allowed for some nice feels. I on the other hand I had a tent peg in my bottoms.
Mom and dad gave us a lot of freedom that night. That was a big mistake! We laid out our five sleeping bags on the floor of the family room in the basement while mom and dad went up to their bedroom on the second floor. The girls made me put my sleeping bag in the middle of theirs. I didn’t mind one bit at all.
As soon as Jean thought the coast was clear she put a stack of empty soda cans in front of the door coming down from the main part of the house as a sort of security alarm booby trap. Then we all got naked. I got to touch and feel them as much as they did me. Then Jean had me eat her pussy to start things out nicely, and nicely was exactly how it was. I knew at that very first taste of pussy that I would never get my fill even if I lived to a hundred. Jean had me eat each of her three girlfriend’s pussies too. Each had a very unique taste of her own and I loved them all. That was exciting! I asked them if I could suck their tits and they let me. Hey, after letting me suck their pussies their tits weren’t any problem at all. I let them all suck my cock too but I didn’t want to waste any of my precious cum on a blowjob so I told them that if I got too excited I wanted to cum in one of their pussies. They all agreed to my request.
My sister Jean was the first girl to receive my cock and my cum in her pussy. It was very quick since I was ready to explode before I even put my cock in her pussy. Too quick in fact if you ask me! I took Jean’s virginity and gave her mine that night. The girls were more excited than I was and kept me hard. Then one by one I took their virginities too. Jean actually got cheated that first time with only a ten-second fuck while that forth girl got about ten minutes with my cock in her pussy. However, being a very horny teenager like I was Jean got me a second time that night. In fact I made sure to get them all twice. No horny teenager could pass up an opportunity like that. I figured that I might never get four willing girls to let me fuck them again, especially not virgins.
That very first night the five of us bonded in a very special way. After that night my sister and I fucked every chance we could. Her girlfriends would come over a lot to let me fuck them too.
Over the next twenty years I was able to get five more fourteen to fifteen year old virgins. Each and every one was just as fabulous as that very first time for me.
About a year ago my sister Jean started talking about old times and reminiscing about that very first time. Actually we talked while we were naked in my bed after having a great round of sex. That’s when Jean reminded me that her daughter Judy was turning fourteen. She suggested that I get much better acquainted with Judy and make some fabulous plans for Judy’s fifteenth birthday and take her virginity. Jean thought that it might be nice for her and her daughter to both give their virginities to me. They would have that in common.
So I started inviting Judy out for dates to the movies and taking her shopping for sexy clothes. Of course I made sure to keep Jean informed of all of my activities.
A month or two before Judy’s fifteenth birthday I mentioned a house that I had rented for the month of August out on Cape Cod in Massachusetts. It comes fully furnished, has an in ground swimming pool, and is right on the ocean with it’s own private beach. Jean was jealous so I told her to come out with her husband and Judy for the first two weeks and then Judy could invite several of her virgin girl friends out for the last two weeks. Jean smiled at that and thought it would be a great treat for them all besides giving me a chance to take Judy’s virginity. Jean even wanted to help out if she could.
Well August arrived and I got to the house a day before Jean and her family. It was perfect. The owners knew exactly what they were doing, there were no televisions, and the phone only allowed outgoing local phone calls. It was the most peaceful place I had ever been. I truly loved it! That night I went for a nude swim in the ocean and lay on the beach counting the stars. It was incredibly peaceful.
The next day when Jean, her husband, and Judy arrived I made them put everything electronic in my trunk and locked it. They were not to have cell phones, computers, games, or anything that the real world considers entertaining. Jean cooperated completely and of course she got her husband and daughter to reluctantly do the same.
After a tour of the inside of the house they picked out their bedrooms and then we toured the outside of the house. The girls loved the flower garden, the beautiful beach, the swimming pool, and the Jacuzzi. As soon as Jean saw the Jacuzzi she suggested nudity only. Of course I agreed immediately. Judy looked at her mother and said that it was okay with her then she looked directly at me and smiled. Jean’s husband said that it was okay if we wanted too get nude but not to expect him to get in naked. I really didn’t want to see him naked anyway.
Jean said that as long as we were there we really should check it out and then she smiled and pointed out that none of us needed to go get our bathing suits on. As Jean started undressing her husband walked away toward the ocean. I started undressing too. When we were both naked Jean gave me a big hug with my semi-erect cock slipping between her slightly spread legs. That did it I had a full-blown erection by the time we got in the Jacuzzi together and watched Judy undress.
Judy was a very pretty girl. Her skin was flawless, her weight was perfect, and her body was sexy as hell. When she was completely naked she turned directly toward me and just stood there smiling at me while I admired her nudity. Then Judy came over to my side of the Jacuzzi and came in making sure that I got a good view of her pussy as she spread her legs to get in and a feel of her tits as she brushed them against my face as she sat down right next to me.
I listened as the two girls talked. Jean told her daughter that I was the boy that she had given her virginity to when she was her age. In fact Jean told Judy all about that very first night right down to the way my cock had felt the first time I slipped it into her pussy. She told Judy about having to share me with her three girlfriends that night too. Then she talked about the way we made love almost every night for years afterwards and that we still make love whenever we can get together.
Judy didn’t seen to want to believe that her mother and I have sex together so Jean sat on my lap in the Jacuzzi with her back to me and slipped my cock up into her pussy. Then Jean had Judy reach her hand down between us and feel for my cock. From the comments that Jean was making it was very apparent that Judy had slipped a finger into her mother’s asshole and had tickled her clit too. One thing was for sure my, cock was buried in her mother’s pussy until I came. Afterwards Judy stroked my cock until it was hard again.
Jean knew what was up from the look in her daughter’s eyes. She kissed Judy full on the mouth while welcoming her to womanhood. Then Jean went to find her husband to try to keep him occupied while Judy and I had sex.
Judy was a lot more eager than I had thought. It seems that she and her mother had talked about sex with most of her girlfriends. She was more than ready to loose her virginity and better yet, to me. Judy liked the idea of loosing it in the Jacuzzi but facing me not backwards like her mother had done it. She wanted to see the look on my face as she sat on my cock. Besides being on top would let her be in control just in case it hurt. However the hot water had softened and lubricated her pussy for quite a while prior to sitting on my cock. I slipped right in easily. She said that my cock felt better than her dildo did. Hells bells, that’s why I slipped in so easily she had already opened it up. It didn’t matter one bit she didn’t need a hymen to be a virgin. Judy was another virgin that I could add to my collection. Judy made virgin number ten!
The inside of Judy’s pussy was actually cool in comparison to the hot water in the Jacuzzi. She got into a very nice rhythm very quickly. I was pretty sure it had something to do with shoving her dildo into herself as she masturbated. Then I felt her hand go down my chest to the base of my cock. She was playing with her clit and using me as her dildo. She got much more serious about fucking me after that and I swear she had five orgasms before I finally cum in her pussy.
Once we had fully recovered we walked hand in hand out to the beach still naked to find Jean riding her husband’s cock in the sand. Judy and I sat down and watched from a distance. When Jean had her orgasm and rolled off of him Judy and I cheered and clapped. They were both red in the face as they realized that their daughter and I had watched them fuck.
Jean must have convinced her husband to walk toward us without putting his pants on first. Judy saw her father naked for the very first time, giggled softly, and then whispered to me that she now knew why her mother liked my cock so much. I must admit that I was wondering why she even married him in the first place. Then I remembered that she was about three months pregnant for Judy when they were married.
We went in the house and made dinner, sat around until dark, then went to bed early. The upper floor had six bedrooms with three shared baths. Jean had picked one of the bedrooms at the far end of the hall while Judy had picked the one right next to mine. Judy and I shared an adjoining bathroom. I think Jean knew that when she suggested that Judy take the room next to mine.
The two girls went into Judy’s bedroom while I went into mine. Jean’s husband must have headed for his bedroom because shortly the two girls walked through the bathroom into my bedroom. Jean told Judy to wear me out, kissed us both goodnight, and locked my door on her way out.
Soon that was exactly what Judy was doing. She wanted me to fuck her as long and as often as I could that night. The first three times were not too bad but getting hard that forth time in about a three hour span was not easy but after Judy sucked me hard that last time I just had to fuck her with it. In the morning neither one of us wanted to do it again before breakfast. I didn’t know about her but I was sure sore. I rubbed some ointment on my cock to help heal it some.
Right after breakfast Jean said that she was going into the Jacuzzi. I thought that it might help my sore cock so I went with her. Soon Judy joined us and said that her father had gone for a long walk up the beach.
I listened as Judy told her mother about the four times we made love last night in great detail. When Judy told her mother that her pussy was sore Jean told her that saliva was a great healer for sore pussies and had Judy get up on the edge of the Jacuzzi. I then watched as Jean ate her daughter’s pussy very slowly for a very long time. Well if it was good for her pussy Judy figured that it would be good for my cock too and offered to suck me. I let her suck me but I kept a close eye out for her father. I didn’t need him catching me fooling around with his minor daughter. My cock did feel better afterwards and Judy said that her pussy did too. I was under the impression that that hadn’t been the first time that Jean ate Judy’s pussy. They confirmed that it wasn’t their first time and that they started eating one another on Judy’s thirteenth birthday.
After lunch we went sight seeing together then ate dinner out before returning home. We sat out on our private beach watching the ocean waves and talking. Judy told me all about the four girls that would be spending the last two weeks with us. She told me their names, who their parents were, and about the boys in school that they each liked. She told me about the one girl with big tits and the two girls with small tits. The other one had tits about her size, which was very nice.
By the middle of the week Jean’s husband was going stir crazy. He could not stand the peace and quiet, no cell phone, and definitely no computer. He was begging Jean to go home early. Finally she gave in and told him to go home if that was what he really wanted to do and then he left.
Jean asked me if Judy could call her friends and bring them up early. She sure could! I let her use her cell phone. I called the Limousine Company to deliver the girls earlier and then locked everything in the trunk again. All of the girls and their parents were okay with them coming out early and they liked the idea of having Jean around as an extra chaperone. Little did they know!
The following day the four girls arrived. We would have three weeks and two days together. The first thing Judy did was to inform the girls that total nudity was the rule in the house, in the water, and out on the beach. Okay! That was simple! Then Judy informed them that she had lost her virginity to me on her very first day here in the Jacuzzi while her parents were fucking out on the beach out of sight. They were ecstatic! Like I had said earlier Jean and Judy had talked with all of them about sex, loosing their virginity, and apparently about what a good lover I was. Wow!
Naturally the girls handed over all of their electronic equipment and then got naked. Judy was right about the one girl with the big tits and about the two girls with small tits. I loved them all though. All four girls told me that they were still virgins but that they really wanted me to be their first lover too. Great!
I started by standing behind one of the small-breasted girls, slipping my hard cock between her legs but not in her, and reached around to fondle her titties as she told me her fantasy about loosing her virginity. I went behind the other small-breasted girl and did the same thing to her as she told me of her sexual fantasy. I then went on to the normal-breasted girl and then on to the big-breasted girl. So as not to leave anyone out I even got behind Judy, slipped my cock right into her pussy, and had her tell them about that first night and our four fucks. I finished up in my sister’s pussy while she told them of our first fuck in the Jacuzzi with Judy feeling her up. I made sure not to cum but it wasn’t easy.
Out of desperation I asked which girl wanted to be first. She gave permission for everyone to be around us and watch too. She sure was fine! Hell she was better than fine! She was the one with big tits and they were firm as my chest laid on them and tried to flatten them out. My sister’s tits flatten out whenever she gets on her back. Her pussy was tight and my cock was dying to cum. She really didn’t know if three minutes or eight minutes had gone by. All she really knew was that I had fucked her and she had been fucked, for the very first time on a beautiful beach facing the Atlantic Ocean with all of her friends around her to share in the experience. In other words she had a fantastic memory to last her a lifetime just as I always try to do for my virgins. I was just happy to cum in someone’s pussy, any pussy but they didn’t have to know that.
By the time I pulled my cock out the other three girls had worked out an order to loose their virginities to me. The normal-breasted girl liked the Jacuzzi idea, one of the small-breasted girls wanted a bubble bath and candles, while the other small-breasted girl wanted to do it in public. It seems that her mother had lost her virginity to her boyfriend in a movie theater. Okay, I was up for everything. I was even going to allow the bathtub girl to use her music from my trunk to help set the mood.
I started with the normal-breasted girl in the Jacuzzi while the big-breasted girl complained about getting sand in her pussy. Jean helped her aim her pussy opening at one of the jets in the Jacuzzi to give herself a douche. It worked and she was happy after that. I knew that the sand would just add another special memory to her loosing her virginity. Anyway the normal-breasted girl loved my cock as soon as it entered her love tunnel. She had been craving a real cock since Judy had mentioned this trip to her. She confessed to playing with herself every opportunity that she could. She talked about doing it every night and every morning in bed, every time she went to the bathroom, and anytime that she thought she could get away with it. She wasn’t alone either because one of the small-breasted girls had been doing the very same thing. In fact she was fingering her clit while watching me fuck the normal-breasted girl. They all were! They thought I was fantastic and at that very moment I thought I was too. The girl that my cock was in was moaning like a cheap whore and I loved it because it was for real. This little woman could be a porn star and I could be her stud. I was ramming her mercilessly as I filled her with my cum. Every one was happy after that because we had all gotten off.
I told the one small-breasted girl that wanted the bubble bath and candles that she would have wait an hour or two. She was just a little disappointed but Jean assured her that it would be a lot better to let me regain my strength and sperm capacity. The other small-breasted girl that wanted to do it in public said that she would settle for a fuck in the ocean at a public beach with plenty of people around. I thought that would be doable! All I needed was a good rest first so we had lunch.
The bubble bath turned out to be very romantic. I slow fucked her to some really boring classical music. I watched her tiny titties quiver as she orgasmed. She orgasmed three times before I filled her sweet little pussy. She had not used a dildo before but her hymen had been broken so it was very tight but it was not painful at all. It was everything that she had ever imagined her first time to be. I was pleased and so was Jean.
All that was left was the last small-breasted girl in the ocean so we all got in our bathing suits and headed out to find a public beach that she liked. It wasn’t all that hard because she picked the very first one that we came across. She was very horny and the last virgin so she was in a hurry. There were probably a hundred people on the beach and twenty more in the water. The seven of us all went into the water together. The girls played around and covered the fact that the small-breasted girl had wrapped herself around my waist and was trying desperately to get my cock into her pussy. The problem was that the water was so damned cold that my erection had shrunk. All of girls cuddled into me in the water to help warm me up plus I got to finger all of their pussies to help me get excited too. It worked like a charm! Before I knew it I was buried in a very nice warm pussy. That was all it took, I was off and running now. I got into a pattern with the waves coming in and together we bounced up and down sort of like what a water bed might do only this was better, much better. Her nipples were rock hard and brushing against my chest as she bounced in the waves. She was shivering uncontrollably when I started to cum but I just figured that it was her orgasm happening at the same time. I was right! When I finally slipped my cock out of her pussy the cold water really shrunk my cock fast. The girls helped the small-breasted girl back in to shore and to her towel. All we needed was for the sun to warm us up because our lips had all turned blue from a slight case of hypothermia. We rushed home to the Jacuzzi and warmed up.
The girls were all extremely happy about how they had each lost their virginity and said that they would highly recommend me to all of their virgin girlfriends, cousins, and sisters.
I was very happy with having de-floured my fourteen virgin but all of a sudden I realized that it was just a drop in the bucket.