Perfect Fit

Let's get a few things out of the way first. I am 27 years old and have problems with women. I am skinny and tall which is not that bad. The problem is that I have a weird shaped dick. When not hard it looks normal. It gets to 10.5 inches long when hard though which is not the weird part. The first 4 inches are about as big around as my thumb. It then widens out so at the base it is as big around as a beer can. One girl laughing at me said it looked like a long pear.

Not many girls have seen me naked. A couple of them either laughed so hard that I never wanted to see them again or were afraid of it. The last girl I had sex with couldn't take me all the way in because of the size at the base. The only girl I had sex with that could take me all the way in didn't like it because it felt like I was stabbing her because the end is long and narrow. To make matters worse, when I cum it isn't the tee spoon or 2. It is closer to ½ cup. The one girl that tried to suck me off couldn't handle the amount of cum and ended up covered. I have to jack off in the shower to keep from making a mess anywhere else.

My best friend since elementary school Bob is married to Amy. Amy is blond hottie. She has a slender figure with breasts that are slightly larger than I like them. Narrow hips and long legs. She is always going around their house in a t-shirt or halter top with no bra and short shorts and her nipple always seem to be sticking out. I think she does that to me on purpose. She happens to be one of the few people that have seen me naked. We were drunk and it was a dare for her not to laugh. She knew of my woman problems as was always trying to set me up on dates. Finally when I gave in she set me up on a date with her friend Jennifer that she works with.

Jennifer is ok looking but no where near as hot as Amy. She is 5 ½ ft and brown hair. Maybe 100 lbs soaking wet. Small breasts and narrow hips. She looked good but put her hair in a pony tail and some braces and you would think she was in the 9th grade or younger. I had her show me her drivers license to make sure I was not being set up as a gag. Unless it was a fake she was 21 at the time. I found out later it was real.

The date went ok. Everything was polite as it was a first blind date. We eventually agreed to get together again the following weekend again. The date ended with a polite kiss on the cheek. The next day I was at Bob and Amy's again having a beer with Bob. Amy had just gotten home from work and told me that Jennifer enjoyed her date and hopped I would have tried for more than a kiss. When I asked her what that meant she said that Jennifer told her that it was first time she went out with someone where she didn't end up feeling like a kid. She told me how Jennifer had told her that in college all the guys took one look at her and thought she was someone's kid sister and off limits.

The next date came and we decided to take in dinner and a movie. Dinner was nice and I let her pick the movie. We got comfortable at the movie I put my arm around her and she put her hand on my leg. I didn't care if I saw the movie and thought about what Amy had said and decided to see if I could get anywhere with her. At least feel her up a little until she pushed me away. She leaned over on my shoulder and my hand slipped down her side to where her breast was. I rubbed my hand over it but got no response as she watched the movie. When she finally noticed what I was doing she giggled and whispered in my ear that if I was trying to get her attention that way I would have to squeeze a lot harder as there was a lot of padding in there. She wasn't upset by what I was doing so I pressed harder. Eventually I was able to feel a small bump in her bra that must have been her nipple. As I rubbed it her hand on my leg started moving.

At one point I heard her moan and she had her eyes closed. Her hand had moved up my leg enough that she was close to touching my still soft dick. I was trying to keep it soft so I wouldn't scare her to quickly. I was still rubbing her nipple though her shirt, bra, and padding when she told me to pinch it. I grabbed it between my fingers and thumb and lightly pinched. She quietly said harder and started to squeeze my leg. As I squeezed harder on her nipple she squeezed my leg harder. I was squeezing as hard as I could with my fingers when she jerked a couple of times and let out a sigh. I released it and she relaxed back into her seat.

She released her grip on my leg and moved her hand putting it on top of my dick. She then leaned over to me. Kissed me on the cheek and asked if I wanted her to return the favor. I told her I would but not now because it would make too big of a mess. She pouted a little but laid her head on my shoulder. Her hand didn't leave my dick though.

She kept giving my dick small squeezes thought the rest of the movie. By the end of the movie I was hard. I mean who wouldn't be. I had to make an adjustment as we got up to leave. Luckily I was wearing loose enough pants that I could put my dick down a pant leg and not cause a scene.

We went back to her place and she asked if I wanted to come in for a drink. I was still somewhat hard and thinking with my small head so I went in. She got us both a drink as we sat on her sofa.

We started kissing again and Jennifer's hands found my dick in my pants. She traced around it with her fingers as we kissed. My hands went under her shirt and up to her bra. She flinched when my hands found the front clasp. She pulled back from our kiss and told me that she rarely let anyone see her chest. She said she wore a lot of padding in her padded bra just to look like she had breasts.

I told her that I didn't mind. I said I understood because I rarely let anyone see my dick as it was not normal as well. She smiled at me and said that Amy had told her about it. I would have to remember to hurt Amy later if this went bad. Jennifer sat back from me and said the classic line "I will show you mine if you show me yours". I nodded to her.

Both of us finished our drinks for some extra courage. She reached down to the bottom of her shirt and pulled up as I stood up and undid my pants. When her shirt came off I could tell she had no cleavage and her breasts were not only small they were tiny. I dropped my pants she looked at the bulge in my boxers. She grabbed the front clasp on her bra and I put my thumbs in my waist band. She undid the clasp and I pushed down some so that the large base was at my waist band.

As she pulled the cups away from her chest some pads fell out. I pushed my boxer down some my dick sprang out. I stared at her chest as I my boxer fell the rest of the way down. All she had was nipples. There was nothing to her breasts otherwise. She reached out to touch my dick and pulled back and looked up to me asking if she could touch it. I told her she could if I could touch her breasts. She told me that her nipples were very sensitive but I could touch them all I wanted.

We resumed kissing and touch each other. Her hands were getting me worked up but I didn't want to cum like this. I knew it would make a mess. I told her that she should back off on what she was doing otherwise there was going to be a mess. She looked around and grabbed her empty drink glass. She resumed kissing me and started stroking me with one hand. Not long later he had me coming in her glass. She kept stroking me and I kept coming in her glass with our lips not leaving each others.

When I couldn't stand it any longer I pulled her hand off my dick leaving the one at the end catching my cum. When I stopped cumming she held up her glass and was surprised at how much was in it. She asked me if I always cum so much. All I could do was nod to her. She held it up to her nose and sniffed it. She said that she had heard that drinking cum would make her breast grow. With that she put the glass to her lips and poured it into her mouth. It took several swallows before she opened her mouth to show me it was gone. She said that it was good and that she was going to have to do that more often. I asked her how often she had done that before. She said that was the first time.

I smiled at her and said that I heard it was better fresh from the tap. She smirked at me and said that she would have to try it that way some time. She sat down her empty glass and crawled on the sofa to me. We started kissing again and her hands went back to my dick that had softened some.

As we were kissing one hand stayed on her chest as the other started roaming her body. Eventually it slipped into her pants. When I got them unbuttoned she lifted her butt and allowed me to push them and her panties down and off her. She broke our kiss long enough to pull my shirt over my head making both of us nude. My hand when between her legs finding nothing but skin. She pulled back again and said that very little had grown in and just plucked the rest. She said that since she looked like a little girl sometimes she liked to act like one and couldn't do that with hair down there as it ruined the illusion. I looked at her questionly and she said she would show me later.

When we went back to kissing one of my fingers easily slipped into her pussy. Another joined it followed soon by a third. She started moaning when the forth one slipped in. My thumb started rubbing her clit as my fingers moved around in side her. She leaned back her head to moan and I leaned down and licked a nipple. Her pussy squeezed my hand and she screeched. Both of her hands left my dick and grabbed the back of my head. She pressed me onto her nipple harder. I kept licking her nipple and moving my finger and she kept screeching and squeezing my hand that was in her. After about 5 licks I sucked her nipple as hard as I could and she started cumming hard. If her hands didn't have a hold of the back of my head she would have bounce away from me. I found that while I was sucking on her nipple if I tapped the end with my tongue it sent a shiver down her that squeezed my hand.

After a couple of time of taping her nipple she pulled my head away from it. She then back away from me enough that my hand came out of her pussy. The way it had been cupped with my fingers in her my palm was full of her juices. I brought up my hand so she could see it and licked all of her juices out of my hand. When she could talk again she said that when she was worked up pressure on her nipples caused her to cum. As long as there was pressure on them she kept cumming and the more pressure the harder the cum.

She smiled at me and said she wanted to try something else if I was game. The night had been going good so far so I told her I was game. She had me lay on my back. She got on top of me and said that she had never done this with anyone else and wasn't sure it was going to work. She said that while she was able to take in something that was wide she was not deep. She had experimented on herself and found at the right angle she could take in something that was narrow fairly deep. She reached down between us and grabbed my dick and lined it up with her hole. She then sunk down on me about ½ way down my dick where I bottomed out in her. She had only made it to the part where I started to widen. She shifted around a little and pushed down. I felt myself slip in further as my head slipped though another opening. I didn't know it at the time but my dick had just slipped past her cervix and deeper into her. She kept sinking down on me and I felt myself bottom out again. This time she had taken me all the way in. She seemed more excited about it that I was. I asked her what she did. She said that she pushed my dick though her cervix to get me all the way in. She said that the end of my dick was inside her uterus and to let her do all the work for a while.

She started moving up and down on me. She would go up until the head of my dick was just about to go though her cervix and then she would go down until I was all the way in again. It was great and I had never felt anything like it before. Her pussy would rub and squeeze the larger part of my dick and her cervix massaged the rest. Try as I might to hold off I let her know I was about to cum again. She told me to grab both of her nipples just as I start to cum squeeze them as hard as I could. She said to not let go of them until I was done.

I held on for a couple of more strokes before I blew and shot another massive load this time directly into her uterus. I squeezed her nipples as I started to cum and it set her off as well. With each of her contractions the top of her uterus hit the head of my dick. It was ultra sensitive because I happen to be cumming at the same time which made me cum more. All thoughts and muscle control were gone. We were stuck in a loop. One of us would contract that caused the other to contract that cause the first one to go again. I don't know how long we were stuck like that but somehow her nipples slipped from my fingers which were still squeezing together. That allowed her to calm down enough to allow me to stop cumming. If that hadn't happened we might have both killed each other cumming to death or at least until one of us passed out. But what a way to go.

She flopped forward onto me as we both tried to catch our breaths. I could feel her nipples poking my chest as we lay there. When I could finally talk again I told her that I was starting to shrink and we needed to move or there would be an even bigger mess on her sofa. She giggled and said that as long as she didn't squeeze we should be fine. I just let her lay on top of me as I felt the head of my dick slip past her cervix. She let out a small moan when that happened but continued laying on me. When my dick finally slipped out of her pussy I expected a bunch of my cum to come rushing out and on to me. Nothing happened though.

When I our breathing had returned to normal I realize it was too late to ask if she was on any birth control. If she was fertile there was no way she was not pregnant now. I asked her about it and she gasped and had a look of horror. She then started to giggle and told me she was safe. I couldn't decide if I was going to throw her on the floor or hug her. I ended up hugging her.

When we finally got up off the sofa still none of my cum had come out of her she stood up and put her hand below her belly button and said that she felt full. I asked her where my cum was and she said that she had it safely trapped inside her but should be able let it out when she wanted. To prove the point she grabbed her empty glass and squatted down in front of me. A moment later a flood of my cum came out of her and into the glass. There had to be at least as much liquid as the cum she caught in the glass last time. She held it up to show me then drank it down. When it was gone she said that she couldn't decide which way tasted better. She would have to try both ways again to try to decide which was better. I just shook my head at her as she started to giggle.

When I asked her how she did that she said her twin sister had shown her last time they got together and she had been practicing with her toys since then. She wasn't sure if it would work but she thought the head of my dick was about the same size as the largest toy she had tried it with. And the fact that I was so large at the base made it even better. She explained how her sister was willing to try things she had never thought of and would tell her about them later. Her sister discovered masturbation first when they were young and her sister was the first to try fisting in college and later showed her that also. There were some things her sister had done that she had yet to try like anal and deep throating. I told her that if she asked me nicely I might be willing to help her try them. When she started laughing so did I.

I proposed to her a week later. Well that was 10 years and 3 kids ago and to this day my wife can still pass for my daughter. Her breast did grow some with the kids but shrunk back up when she stopped breast feeding. I met her sister the first time when she came in for the wedding. They looked and acted identical in almost every way. Both internal and external if you must know. With her sisters help we did find out that you can't cum to death and I pass out first but that is another story.