Learning about Sex
My best friend Jenna lives next door to me on one side and her boy friend Tom lives next door on the other. We all grew up together and attend the same school. Jenna and I have been having sleep overs for years but I never told her about my special parts. One Saturday when we were 13, my parents had to go on a trip and would not be back until Sunday evening so Jenna came over to spend the night.
As we ate pizza for dinner, Jenna told me that she and Tom, who was already 14, had been “doing it” for a couple of months. I asked her to tell me all about it. She said they had been going together a couple of months when he asked her if she was ready to have sex. She told him that first she wanted to think about it and second, she did not want to take any chances. The next week she told him that she was going on the pill and that they could both lose their virginity together as soon as she was safe. They read several virginity stories together and Tom promised to take it real slow and easy when the time came.
Three weeks later her parents went out for a late evening so Tom made a big show of bringing over a new movie for them to watch. As soon as her parents left, they went to her bedroom, got out an old towel to cover the bed, undressed each other, took turns inspecting each others naked bodies and started to kiss and fondle. He kissed and sucked her breasts as she stroked his member. He tickled and rubbed her pussy before gently inserting a finger. He run that finger up and down her slit, tickled her clit and pushed gently on her cherry. Jenna said by then she was so horny that she told Tom to stop fooling around and they should just do it. Jenna put her ass in the middle of the towel, spread her legs and pulled Tom down on top of her. Tom rubbed his dick up and down her wet slit a couple of times and then placed it against her hole. She said he pushed just a little bit and the head slipped inside. He pushed just a bit more and her hymen stretched and finally broke. She said that it hurt for a a minute or so but the pain soon stopped so Tom continued to slowly push into her. Once he was all the way in, they stopped and savored the feelings for a bit before Tom started to move in and out slowly at first and then faster. The feelings became very intense causing Toms member to swell even bigger before he shoot his load. Toms orgasm caused Jenna to have an organism as Tom fired rope after rope of cum deep into her no longer virgin virgina. After they had both calmed down, they noticed that there was a pool of blood and cum on the towel.
Since then they had fucked every chance they got. I asked if they had tried oral sex and she said yes, she had done him and he had done her. They both enjoyed oral sex but like fucking even more.
By now we were both feeling really aroused. Jenna asked if I would be interested in trying oral sex with her? She said she had never tried girl on girl sex but she she had heard that it felt really good to have your pussy licked while you licked a pussy. I said that she was my best friend and I would do anything for her. I said that there was a secret that she had to help me keep – that I had a very unusual set of genitalia and if the word got out around school, I was afraid I would be treated like a freak. She said that was no problem and that I should not tell anyone about what she and Tom were doing either. I then told her about my retractable penis and that I had a complete set of male and a complete set of female parts. Now her curiosity was really aroused and she had to see for herself.
We throw back the covers and we both took off the long T-shirts and panties we were wearing. I showed her that I had a pussy and then I made all 5 inches of my penis appear. She felt and stroked both and decided that they were real. I asked her if she wanted to have girl on girl sex or boy on girl sex? She said she wanted to try both but since we had been talking about girl on girl oral sex we should do that first.
Jenna lay back and spread her legs to reveal a pussy covered with just a bit of light brown hair. I lay on my stomach and positioned myself between her legs. First I tickled and rubbed her slit for a minute before I spread her labia and got my first real closeup look at a pussy. I then licked up its entire length and kissed around the top of her slit. She tasted good. She started to moan and really jumped when I licked her clit. I licked up and down her slit a couple of times before sticking my tongue in her virgina as far as I could. I wiggled my tongue around and she started to moan even louder. I moved back up to her clit and started to really suck on it while inserting two fingers into her virgina. Jenna started to pant and then stiffened up as she orgasm-ed and squirted girl juice all over my face.
I told Jenna that I also wanted this to try girl on girl oral so I would hold my penis out of the way so she could focus on my pussy. I lay back and spread my legs while holding my penis flat against my stomach. Jenna positioned herself between my legs and started to kiss her way up my thighs to my pussy. It felt really wonderful when she licked up and down my slit. It felt even better when she inserted her tongue into my virgina and moved it around. Since I was already really excited and stimulated it did not take but a minute or two for me to have an organism. Since it is mostly the same nerves that control both my male and female parts, when I have an organism, my virgina secretes extra moisture while my penis shoots a load of cum. There was enough vaginal fluid to get Jenna’s face wet and a really big pool of cum collected in my belly button. Jenna was amazed at the quantity and just had to taste it. She said it tasted a bit different from Toms but that it tasted good. She then proceeded to lick my belly button clean.
Jenna asked if I had ever had oral sex as a boy? I said no but that I had heard that blow jobs felt really good. She said that she have given Tom a few and that he sure liked it. Jenna proceeded to stroke my penis a few times to get it to stand up again. She started to lick its full length on both the top and the bottom. After taking the head into her mouth she started to lick it like a lollypop. That felt wonderful. Jenna started to take more and more of my five inches into her mouth. She was able to take most of it and the feeling were getting really intense as I played with a tit with one hand and her pussy with the other. I warned her that I was about to cum but she just waved and sucked harder. I fired a full load down her throat. She hung in there and was able to swallow it all. I asked her how she was able to do that? She said she had been practicing on Tom.
At this point both of us got out of bed, stretched and went to the bathroom. We decided to take a break, get a drink and rest for a few minutes. Jenna asked if I was a virgin? I said yes, technically I was a virgin as both a man and a woman because I had never fucked either a boy or a girl. I mentioned that I no longer had a hymen. I then told her the story of how I broke my own cherry. I explained that I could not really fuck myself because my penis pointed the wrong way. When it was semi hard, I could rub the head of my pen is along my slit and even get the head a short distance into my virgina. As my erection got harder, it would pull itself out of my virgina and try its hardest to point up and out. I had never managed to cum in my own virgina.
Jenna asked if I was ready to lose my male virginity? I said that I was more than ready so she led me back to bed and do boy on girl sex for real. She suggested that we start with the traditional missionary position. She hopped into bed, laid on her back and spread her legs. I asked her if any foreplay was required and she said no just kneel between her knees and aim my penis as I leaned forward. I did and with just a little bit of guidance from Jenna, my penis found its way into her virgina. She raised her knees and I slid all the way into her hot snatch. I started a slow rhythm and she pushed back each time I pushed in. It felt wonderful. My guy feelings took over my brain and I started to pump faster and faster. Jenna locked her legs around my back and pulled me in even farther. I felt a huge orgasm building. My penis swelled bigger than it had ever been and then with a shout and a groan I fired rope after rope of cum as deep into Jenna as I could. She felt herself being filed and experienced her own orgasm. I lay on top of Jenna with my penis still in her for several minutes enjoying the afterglow from our hot sex. After I finally rolled off of her we were both sleepy so we pulled up the covers and went to sleep.
When I awoke, wonderful feelings were radiating through my body. I looked down to see Jenna sucking on my penis while fingering my pussy. Jenna stopped, smiled and said good morning. I smiled back and told her how great she was making me feel. I ask Jenna what I could do to make her feel good as well? She said she wanted to do more boy on girl sex and to try different positions. She got up on her hands and knees and suggested that I move around behind her and enter her pussy from the rear. I moved around behind Jenna, saw her pussy gaping open and inserted my penis. She was already wet so I slid right in. I began to hump her while I tickled and pinched her nipples. She immediately started to moan and pant. She told me it felt like I was even deeper than I had been last night. I started to hump faster and harder and soon I began shooting ropes of cum deep into her hot snatch. She moaned really loud as her sphincter clamped down on me and held me deep inside her until we had both finished our organisms.
We decided that the next stop was the shower as we both needed one. We got into the shower together, turned on the water and started to soap and wash each other. She washed my penis and we each washed the others pussies. Jenna said there were a number of other positions we could try. Her first suggestion was to stand face to face. I was over an inch taller than Jenna so I had to squat about 6 inches in order to point my penis at her pussy. She held her labia open and my penis slid right in. The straighter I stood, the deeper into her I went. Again it felt great so I started to gently hump her. Jenna said that this position seemed to work well for us and suggested we stop, dry off and try some others.
After we were dry, Jenna bent over the vanity table, spread her legs and asked that I try for a rear entry. That also worked well as I was able to slide in easily and go quite deep. After a few test humps, Jenna wanted to stop and go back to bed.
Jenna said we would next try several girl on top positions. I lay on my back and held my penis as Jenna straddled me and sat right down on erect penis. Again it slid right in. In this position Jen could could move up and down on me or I could hump her so we tried both and decided that it worked best if she set the pace and I met her downward moves with an upthrust of my own. We tried this position with Jen facing forward on me and then reversing to face backward. We liked the forward facing position better because the clit to penis contact was better. Each time we stopped after a few test humps.
The next thing she wanted to try was for her to lay half on and half off of the bed while I stood between her legs. To get the heights right we had to put two pillows under her ass. With the alignment about right, I pushed into her and really started to hump. I think we both really needed relief because she told me she was ready for the biggest cum of her life and now was the time for me to give it to her. I fucked her as hard and fast as my 13 year old athletic body could manage. Right then my guy feelings were at saturation and my nervous system was shifting into overload as she rubbed my tits and I rubbed hers. It did not take very long for me to start shooting rope after rope of cum into her. She also had a mind blowing organism that shook us both. After we calmed down, we decided to clean up and have breakfast.
During and after breakfast we discussed all of the things we had done and how we felt about what had happened. I told Jenna how much I loved her and what a special “best friend” she was. Jenna said she was honored to be the one to teach me about girl on girl sex, to help me lose my male virginity and to teach me some of that boy on girl sex stuff.
We talked for most of the morning before Jenna asked me how I planned to lose my female virginity? I said I was ready to do it but that I had no idea how to make that happen. Jenna told me one of her fantasies was for the two of us and Tom to have a three-way. We discussed several possible positions and tried to imagine what it would be like. I asked Jenna if she would be jealous if Tom and I had sex? She said no but she definitely wanted to be there and watch. I asked her if she thought Tom would be interested in joining our sex games? Are you kidding, she answered, he is a very horny 14 year old male with a vivid imagination. Of course he would jump at the chance to have sex with the two girls he likes best. He likes me? I asked. Of course he likes you, she said the only reason he never asked you out is that you haven’t started dating.
Jenna picked up the phone and called Tom. Tom said he was just hanging out at home and wishing he had something interesting to do. We invited him to come over. We unlocked the front door, got naked and jumped into my parents bed. When we heard the front door open we yelled that we were upstairs in bed. He bounded up the stairs, found us naked and started to strip. We jumped up and helped remove his clothes.
Once he was naked, we sat him on the bed and said that we had to have a serious conversation. First, I said that I had a a secret that he had to help us keep and second, I needed a huge favor. Since almost any horny, naked, teenage male who is looking at two gorgeous naked girls will automatically agree to anything, Tom immediately agreed to help me with whatever I wanted and promised not tell a sole.
I explained to Tom that due to a freak of nature and I had two complete sets of genitalia,, one female which he was eagerly eyeballing and one male which were concealed inside of me. I told him that I was a true Hermaphrodite, a Hermie. He looked shocked and confused. I stood in front of him, spread my legs and showed him my pussy. Then I slowly turned all the way around while commanding my penis to appear. By the time I was facing him again, my penis was starting to emerge and as he watched, it grew to its full 5+ inches. I stood still as he first did a double take and then slowly reached out to feel first my penis and then my pussy. After convincing himself that both were for real, he asked me how he could help?
Jenna and I told him how she had taken my male virginity yesterday and that I wanted him to take my female virginity today. That got his attention. His penis, which had mostly deflated while we were talking, suddenly sprang to its full 7 inch length. His penis was not only two inches longer than mine, it was at least twice as thick. I did not worry about that, my virgina had been stretched a lot during all of those examinations.
Jenna and I both wanted to watch my official deflowering so we had Tom lay on his back. I climbed on top of him and started kissed him while I rubbed my tits on his chest and my pelvis against his. I was enjoying this whole new set of “girl feelings” as his penis rubbed around my crotch. (I do not know how he felt about having my penis rub against his.) He played along by tickling my tits with one hand while fingering my pussy with the other.
When I was nice and wet, I straddled him and announced that I was officially ready to become a woman. While I held my penis against my abdomen, I centered my virgina over his upward pointed pole and slowly sank down onto it. The head slipped in easily and as I relaxed my sphincter muscle the shaft followed. I slowly lowered myself until my pubic bone was resting on his and all 7 inches were filling and stretching me more than I had expected. I started to move up and down an inch or so and tried leaning forward and back until I found the position that felt best. Tom started to thrust up each time I slid down and that felt even better. I was producing so much lubricant that we soon started to make squishing sounds. Jenna, who had been watching from over Tom’s shoulder, decided to get in on the fun by fondling and licking both my breasts. That really got my “girl feelings” going. I increased the length and speed of our strokes which made the feelings even more intense. It must have been the same for Tom because I could feel his penis begin swell even more as he announced that he was about to cum. He held me down as I felt his penis throb and twitch as he fired the first rope of cum and then quickly repeat as he fired 4 or 5 more cum balls deep into me. As he was shooting his cum into me, my senses overloaded and I had my own organism. My vaginal muscles clamped down on him and they milked him for every last drop of cum. At the same time, I shot my load of cum all over my stomach where some of it splashed all over his abdomen. We stopped moving, held our positions and just enjoyed the afterglow. After a minute or two, we both found our voices and said “WOW, That was terrific.” I eased off of his deflating penis and moved forward to let his cum drip out of me into my cum puddle on Tom’s abdomen. Jenna took charge of licking up all of the cum. She not only licked up the joint puddle, but she licked both penises clean as well as my snatch.
We decided to take a break, have lunch and talk about what we wanted to do next. As we made sandwiches, Jenna told us about her fantasy of having a three-way sex sandwich. As we ate, we discussed the idea and the possible positions. The more we talked about it the more excited we became. This was going to be a totally unique experience.
We headed back upstairs to the big bed to put Jen’s fantasy into action. Jen lay on her back and was to be the bottom layer of the sandwich. There was no choice but that I be the middle layer of the sandwich so I got between Jen’s legs and inserted my penis into her snatch. After a couple of test thrusts to spread our lubricants, I lay forward, tit to tit, on Jen and spread my legs. Tom keeled between both sets of our legs and worked his big cock into my pussy. When he was most of the way in, he started a slow steady rhythm. Each time he pulled back, I would also pull back. Each time he pushed into me, I would let the force of his thrust push my penis into Jen. It felt great. Both my girl feelings and my boy feelings were starting to go wild. This was the ultimate stimulative overload, Tom’s dick pumping away in my pussy at the same time my penis was pounding Jen’s pussy. I did not last very long. I soon let out a long, low moan as I experienced a massive double organism. While I was shooting cum balls into Jen, my vaginal muscles were gripping and massaging Tom’s cock. Tom did not miss a beat, he kept right on humping me which meant I kept right on humping Jen. It also meant that both my virgina and penis continued to stimulated. We had not planned this but I was now heading into multiple organism territory. Tom gradually speeded up the pace so Jen and I followed his lead. I was now moaning with every thrust and Jen was starting to moan as well. Tom was starting to pant and hump harder so I knew he was getting close. I could feel his penis start to swell which sent me over the edge again. Again I experienced a massive double organism. As I started my organism, Tom drove his dick deep into me and started to fire his load of cum. He drove me deeper into Jenna as I fired a second load into her. That drove her over the edge and we experienced our first triple cum together.
We lay together I the sandwich position until we could catch our breath and get our emotions under control. We slowly untangled our bodies and sat up on then edge of the bed. The first thing we noticed was the size of the pool of cum on my parents sheets. It was huge and cum was still dripping from Jen and me. The second thing we noticed was how completely satisfied we all felt. We headed for the showers and then get dressed. We stripped and remade the bed, washed the sheets and prepared for my parents return.
We discussed how we felt about our joint experience, our feelings toward each other, what we wanted in the future. We agreed that today’s three-way was not only the most mind blowing experience we could imagine but was also the best sex we had we had experienced. We decided we had to arrange to repeat that experience as often as possible. And we did.
Most days we would meet after school for S. & S.(snacks and sex) at which ever house had the best snacks and the parents were still at work. If one of us had sports or something right after school, the other two would meet and fuck like rabbits. We were truly Fuck Buddies. When we heard the term “Friends with benefits”, we thought that described our relationship even better.
Continued as: Continued as: My Life As A Hermie – Growing Up