Before I type any further I want to stress that what followed was consensual.
I once had this babysitter named Joan*. I call her Joan because she reminded many people of Joan Jett. Not the tough and intimidating Joan Jett, but the sexy and always smiling Joan Jett. She was my parent's go-to sitter for my brother and I for many years. I was in early grade school and I had a definite crush on her. She usually brought a friend over with her when my parents went out, and she always wanted us to go to bed early so that they could hang out. I would often refuse to go to bed unless she gave me a kiss. I would always try and kiss her on the lips, but as she was much older and wiser and I was utterly transparent, she would always artfully give me a peck on the cheek and avoid my questing lips, and I would unhappily sulk off to bed. My life changed a lot when my parents divorced. Being very sensitive, I withdrew, and Joan got older and got a real job and moved on from sitting. She was five years older than me, and although we went to the same school (being in a small town k-12 was all in the same building) I have no memory of ever seeing her in school again.
*fast forward 10-15 years*
I was in my mid 20's and was out at a local bar. Now many here know that I am transgender, but at this time I was able to pull off being all boy. I was out with friends and I happened to look over and see this woman sitting at a table with someone who happened to be a mutual friend. After all of those years I instantly recognized her, and my crush resurfaced in that moment. It was Joan. I walked over and started a conversation with our mutual friend, and looked over at Joan and asked her if she recognized me. She did not (DAMMIT! Oh well, I was like 10 the last time we had seen each other). We talked on and off the rest of the night, and when the bar closed quite a few people ended up at my house (it was the local den of iniquity at the time) and for the rest of the night, if Joan and I were not talking to each other, we were staring at each other while trying to talk to others.
Needless to say, we hit it off and began dating. She had moved to a town about an hour away, and we took turns spending the weekends at each others' homes. This lasted for about three or four years. Of course we got into the kinky stuff. At some point during our relationship, she related a fantasy to me. A rape fantasy. I balked. Several times. She continued to bring it up every so often. Finally I agreed to give it a try.
Now before I go on and describe what happened, I want to say that the reason I wrote the back story was to illustrate that not only were we in a relationship of some duration, but that we had a history together that gave us an incredible amount of trust, and that this was something that was brought up and discussed repeatedly before it happened. I would never endorse doing this unless both parties were very comfortable and were absolutely certain that it was what they wanted.
We decided that this would happen on a given weekend, but not on the night it would occur, so that she would not know exactly when I would show up, and the surprise value would be as high as possible. We agreed that there would be no communication between us in the week leading up to the event. I chose my night and went to bed early, setting my alarm for midnight. I woke up, showered, and set off for her place, which was an hour away. I pulled into the parking lot at about 2:30 AM and parked in a spot some distance from her door. She lived in a townhouse and her entire building was dark, even the neighbors were all asleep.
I walked across the parking lot, very quietly let myself into her door, went into her kitchen and got myself a glass of water. I had absolutely no idea what I was doing. I had not planned anything out (this has always been a weakness of mine) I remember standing there for a good 20 minutes trying to come up with a plan. I finally gave up and went upstairs.
I tiptoed into her room and there she was...fast asleep, laying on her back. She looked so lovely laying there, so peaceful. I decided to improvise. I sprung up into the air like some kind of spider-man shit, and came down on her landing on all fours, straddling her. She screamed. I bet every single person in that group of townhouses heard it. I slammed my hand down on her mouth. Her eyes looked to be the size of dinner plates. The fear I saw there was shocking, and her body was as stiff as stone, but it only lasted a moment. Her eyes finally focused and she looked up at me, realizing who it was, and I grinned down at her. She relaxed.
Then she bit my hand!
I yanked it away and saw the grin that had been hidden behind it. I slowly shook my head and said something like "Oh you are mine now you bitch" I yanked the covers off of her and roughly flopped her over onto her stomach. Grabbed a handful of her hair and shoved her face into her pillow with one hand and yanked her panties off with the other. I lowered myself onto her back and whispered into her ear, telling her that I was going to use her and leave her broken. She started shaking (she did this when she got excited) and I very clumsily pushed my pants off with my free hand, while still holding her head down with the other. I lowered my hips onto her ass, and went back to whispering crudities into her ear, and I am sure she could feel me getting excited. I slipped my knees between her legs and used them to push her legs open. I placed my free hand on her lower back, pinning her in place. I then had my way with her. She immediately began quietly whimpering, and then began moaning like a naughty girl a short time later. I do not know how long it lasted for sure, but I would guess 15-20 minutes. I never allowed her to move. She would occasionally try to reach back in my direction with her hands, but I would just slap them away, and go back to holding her down. I was as rough as I felt I could safely be.
After I finished I lowered myself onto her back and viciously instructed her to count to 100 before she lifted her face from her pillow, and then I got dressed and left. I looked over my shoulder at her as I left her bedroom- she was whispering numbers.
I had mixed feelings on the way home. I had no doubt she enjoyed the experience, but I was still unsure about how I felt about the whole thing. I got home before dawn and collapsed into bed.
When I woke up there was a message on my machine. I pressed play. It was Joan: "I love you. Please come down for dinner and spend the night with me." So I drove down to her place once again.
She met me at the door , put her arms around me, kissed me passionately and led me by the hand into the kitchen.I no longer had mixed feelings. She was very happy and content. We sat down and had dinner and she described how exciting the experience was for her. We did the dishes together, and then snuggled up in front of a movie for the rest of the evening.
This post will probably self destruct in the morning when I wake up.