This is a work of fiction and the story idea came from: Triple Sex Ultimate by blueheatt
For more information on this topic I suggest the book Middlesex by Jeffrey Eugenides .
This part three of Randi’s story. The story is much more understandable if read in sequence.
The Girls Sleepover or My First Cherry
Jen and I often talked about our sexual fantasies. When I was 14, I mentioned that one of my fantasies was to actually be the one to take a girls virginity. To try to make that happen, Jen and I decided to have a sleepover at my house and invite our good friend Sue to join us. She lives in the neighborhood and has been in school with us for years. We chose Sue because we knew that she was a virgin, she had recently asked us questions sex and she was not a gossip.
Sue came over on Saturday afternoon, said hello to my parents, we ordered in Pizza and retreated to our basement TV room. As we ate, we brought up the subject of sex and asked Sue if she had a boy friend? She said no, but that she had been to several parties where everyone had paired off to talk, kiss, and maybe feel each other up. We asked her how far she had gone? She said she had not gone past 2nd base (kissing and letting him touch her breasts.) She really wished she had a boyfriend because she was ready to learn what all of then shouting was about. She said she had discussed her sexual fantasies with her mother who had told her to be patient, that it would happen, but just in case she was now on the pill.
Jen and I smiled at each other and told Sue that we had secrets to share but that she could not tell a sole. The first secret was that Jen and her boyfriend Tom had been doing it for a while. She said she would keep all of our secrets and that she was not surprised by the news about Jen and Tom. We then told her that I had some special parts that she and Jen did not have. She looked confused and asked what we were talking about? I told her that due to a freak of nature I had two complete sets of genitalia, one female which were in the normal places and one male which were tucked up inside. I told her that in addition to a virgina, I had a retractable penis. She still looked confused so I said I would show her as soon as we had finished eating. Jen then told her that my male parts really worked and that she and I also had sex regularly.
I said “OK kiddies its show time” as I stood up, turned on some music, removed my sun dress, folded it, and put it on a chair. My bra and panties followed. I stood naked in front of Sue for a minute before spreading my legs and showing her my pussy. I then slowly turned all the way around while commanding my penis to appear. As everyone watched my penis appeared and inflated to its full 5+ inch length. Sue could not believe what she was seeing. She had to touch both my penis and my virgina to make sure they were real. While this was going on, Jen removed all of her clothes.
I grabbed a cushion off of the sofa, threw it on the floor and stretched out on top of it. Jen straddled me and slowly knee walked herself into position so I could enter her. Everyone watched as I slowly moved my penis up and down the length of Jen’s slit to stimulate and spread her moisture. Jen and I both tickled and massaged the others breasts which made us both moan. When Jen thought she was wet enough, she started to lower her pussy and we watched as all 5 inches slid in. Jen then made a big show of changing from short strokes to long strokes and demonstrated slow, medium and fast paced strokes. We then rolled over so I was on top and tit to tit with Jen. I pulled all the way out and then slammed back in a couple times so Sue could get a full view of the action. When I was ready to cum, I pulled out and shot my load on Jen’s abdomen. Sue was totally blown away.
She just watched in shocked amazement as my penis slowly deflated and then retracted. As I handed Jen a couple of napkins to wipe up the mess, a whole stream of questions flowed from Sue. First she asked if the stuff I shot was what made babies? We said yes, that was semen or cum and that there were millions of sperm swimming around in it. She asked if my penis was about the same size as other boys? I told her that mine was a little smaller than average. Jen told her that Tom’s was 2 inches longer and twice as thick. Next she wanted to know what sex felt like? We told her that it was really hard to describe but that it felt wonderful. We then tried to describe how an organism felt. We quickly gave up and suggested that we help her to have one or more so she would know. We told her there were at least three ways to have an organism – masturbation, oral sex and vaginal sex.
Sue had tried masturbation but did not think she had ever had a real organism. We suggested that if she would also get naked, we could fix that. She nodded so we helped her remove her dress, bra and panties. Sue was medium height, slender, had beautiful red hair on her head and a somewhat lighter red neatly trimmed bush. She had beautiful B cup breasts that stood up nicely without a bra. Her nipples were small, about an inch long and were standing straight out. She gasped when I took her long nipple in my fingers and started to roll it around. I pinched both of her nipples and they got even harder. Jen then started to lick around one breast while I played with the other. Sue was really starting to pant and moan. While I sucked on one breast, my fingers slid down her abdomen and started to play with her pubic hair. I was not surprised to find that Sue was so wet that she was dripping. I rubbed her mound and must have touched her clit because with a moan and a shudder she had her first real organism. We sat her down on the sofa, let her recover for a minute and asked her how it had felt? Her one word reaction “WOW!
We suggested that oral sex might cause her to have an even bigger organism. She immediately agreed and asked what she should do? We told her to just lay back on then sofa and we would do the rest. Jen began by kissing her on the lips, moved down to kissing her breasts, and then began kissing all around her abdomen. As Jen spread her legs and began to lick her slit, I kissed Sue and started to work my was down to her breasts. As I began to lick and suck her nipples, Sue went into stimulation overload and had a second, even larger organism. Jen and I kept right on licking and sucking and a couple of minutes later she had her third organism in about ten minutes. Jen and I stopped to let her catch her breath as we got ready for the main event.
There was no doubt in our minds that Sue was completely ready to lose her virginity so we did not even ask. We piled two sofa cushions at the end of the sofa and asked Sue to put her but on the arm of the sofa with her legs hanging over. I stood between her legs and asked Sue if she could see the action? She said no so we got another pillow to raise her head so she could watch her own deflowering. With an dramatic “Ta Da” I commanded my penis to extended and then began to rub it up and down Sue’s wet slit. I even rubbed the head against her clit a few times to really get her in the mood. Gently I pushed into the entrance of her virgina and the head of my penis slid right in and up against her barrier. I gave a gentle push and the only thing that happened was a cry from Sue. I decided the best thing to do was to get it over with so I gave a big push that tore right through her hymen. I held very still until the pain subsided. Jen kissed her and wiped away the tear in each eye. After a minute or so Sue nodded for me to continue. I began slow gentle strokes that soon had Sue fully impaled. As I gradually increased the pace, Jen tickled and massaged her breasts. Sue’s breasts must have been exceptionally sensitive because almost immediately she had an organism which caused her vaginal muscles to really clamp down on me. I kept on pumping faster and harder as my organism built. I told Sue that I was about ready to cum and that she should be able to feel it when I shot my load into her. She nodded and began to hump back against my strokes. Within a minute my penis swelled even more as I shoved all the way into Sue and fired cum ball after cum ball into her. That caused Sue to have another organism during which her vaginal muscles squeezed and milked me for every last drop of cum.
Sue and I were completely spent and drifted off into our own spaces to enjoy the afterglow. Jen licked the extra cum off of both of us, got dressed and then helped both of us get dressed. We put the rec room back together, collected the pizza remains and headed off to my bedroom. We spent much of the night discussing our feelings and reactions.
Dating
When I was 14, my parents and I had several discussions about my sexual orientation and how I might plan to live my life. We had already decided that since I looked like a girl, I should continue to dress and live as a girl. I had told my parents about my relationship with Jen and Tom and they were OK with me having sex with either or both of them. I also told them that I was truly bi-sexual. I had girl feelings that included being attracted to good looking guys as well as enjoying vaginal sex. I also had guy feelings which included being attracted to and wanting to fuck good looking girls. I found sex as a man to be just as enjoyable as sex as a woman. The question was how do I arrange my life so I can do both and still be accepted as a “Normal” person.
The question of dating brought some urgency to these discussions. I had been on a few “group dates” where a car load of kids would go out together for food and fun. The ones I was on involved lots of talking and getting to know each other but not much else. I had also been to a few parties at someone’s home where we danced, talked and maybe kissed and petted a little. I asked my parents advice about what to do when a guy asked me to go on a real date? We talked about that a lot and they suggested that I let the relationship develop slowly. Kiss him goodnight after each date but stay out of sexual situations for as long as possible. (Sounds like what most other parents tell their 14 year old daughters.) My parents did suggest that when it looked like a situation was becoming seriously sexual, that I stop, stand up and tell my date that we have to have an important, private discussion. Depending on his reaction I should then explain that I am a Hermie and have a penis as well as a virgina. Based on my prior experiences, his reaction would be “OK prove it” to be followed by a show and tell session.
I am now 16 and have been dating guys for over a year. The most interesting guys were all two or three years older, have cars and plans to attend college. Two of those relationships reached the sexual stage. In both cases after dating a couple of months, our feelings for each other grew stronger and it became necessary for me to have “The Talk” with them. The first time we were in my basement TV room while my parents were upstairs. I calmly explained that while I looked like a girl and had a complete set of working girl parts, I also had a complete set of guy parts tucked up inside and that they also worked just fine. I explained that I was a Hermie. I described my retractable penis and offered to show him both my penis and my pussy. He accepted the offer immediately. Maybe he was curious about my retractable penis and maybe he just wanted to get a good look at a pussy, any pussy. (He had told me earlier he was not a virgin but I don’t think he had done it more than once or twice and probably in the dark.)
I put on some music and stripped as I danced for him. I stood naked in front of him and let him get a good overall view of my body. I then spread my legs and labia so he could get a really good close look. As always I did a slow twirl as I commanded my penis to appear. He watched with fascination as it inflated to its full 5 inches. I asked him what he was thinking right now? He told me he did not care about the penis. He thought that I had a beautiful woman’s body and right now he just wanted to get naked and get it on. He then proceeded to get naked. His penis was about an inch longer than mine and a good bit thicker. I grabbed a handful of paper napkins and explained that since the same nerves are hooked to both my male and female parts, when I had a girl organism my penis still shoots cum all over. I suggested we use a rear entrance position as I bent over the end of the sofa and spread my legs. He immediately got the idea and his penis entered me smoothly. Unfortunately he was so excited that he fired his load in less than a minute. I told him that was OK just keep humping. He did and after several minutes I had an organism. My pussy muscles started squeezing and milking him which caused him to have a second organism. With both of us satisfied, we cleaned up and got dressed. I asked that he not tell anyone that we had had sex or that I was a Hermie. He agreed. That relationship continued for only another month. His father got a new job and the family moved away.
The second relationship followed a similar pattern. After a month or so we found ourselves alone in his home one evening. He brought up the subject of sex and expressed his desire to take our relationship to a more intimate level. Again I gave “The Talk”. He had never heard of a Hermie and asked lots of questions about my body, my life, and what I could and could not do. He was both fascinated and a bit weird-ed out. He asked if I was willing to show him my body? I said yes and asked if he wanted to undress me? That seemed to help. As he pealed off each layer, he had a stronger guy reaction to seeing and feeling an increasingly naked female body. Once totally naked, I stood still in front of him and let him ogle my body. I then spread my legs and labia so he could get a good close look. As always I did a slow twirl as I commanded my penis to appear and snap to attention. He had even more questions like could I fuck myself? I told him no because my penis pointed the wrong way. I did tell him the story of hows I broke my own cherry at age 12. He asked if I had tried sex with both boys and girls? I told him I had lost both my virginities when I was 13 and that I really enjoyed sex either way.
I told him I had strong girl feelings for him and really wanted him to make love to me. That must have been the signal he was waiting for because he got naked in about ten seconds. When we compared penis sizes, it was no contest – his was three inches longer. I asked for something to catch my cum and he handed me his underpants. I asked him if he had ever tried doing it doggie style. He said no but he would like to try that. I dropped to my knees, spread my legs, and leaned forward. He immediately got into position behind me and started rubbing his long dick up and down my slit. As soon as it was lubricated, he slid into me and started to hump. By the third or fourth stroke, I could feel his balls slapping against my ass. His was the longest dick I had encountered and it felt really good to have it pushing against my cervix. We settled into a rhythm of long strong strokes that allowed me to rock back as he stroked forward. It felt great! It felt even better when he reached under me and began to massage both breasts. I soon went into sensory overload and had a strong organism. I guess my organism triggered his because a couple of strokes later he drove balls deep into me and held it there as he fired a full load right into my cervix. By now my head and shoulders were resting on the carpet. I just stayed there and enjoyed the after glow. We decided that this was so much fun, we did it twice more before he took me home.
That relationship lasted until he left for college. I do not have a boyfriend at the moment. Tom, Jen and I still meet for S. & S. (snacks and sex) after school several times a week so none of us suffer from sexual deprivation.
There are at least three reasons to date: to improve your social skills, to try to get laid and ultimately to find your life mate. I am not sure any of the three apply to me today. My “friends with benefits” relationship with Tom and Jen take care of the first two. At age 16 I have no idea whether I ever want to get married or if I did would it be to a man or a woman. I also have no idea if I would ever want to get pregnant and have a child or for that matter whether I would ever want to father a child. It is possible for me to impregnate myself, but that is probably a very bad idea. It would not be a good idea genetically, financially or socially. Imagine trying to explain to the clerk at the hall of records that you are both the biological mother and father of the child you want to register.