Anthony/Toni

When I was 15 I was hanging out with some bad guys. We robbed a store, I got caught and went to jail for five years. Anthony, my brother, was only ten when this happened. When I got out of prison my parents told me to not come back to the house. So I moved out of town.

Five years after getting out of prison things weren't going well for me. When you are an ex con it is hard to find a job. It is even harder to find a woman who will go to bed with you.

I moved back to my hometown; I figured I hit up some of my old friends for a job. So I went to a networking party. At the party there was a woman. She looked vaguely familiar; I thought I must have known her in first grade or something. She started a conversation with me and seemed friendly. She wasn't a knock out, but I hadn't had sex in over eight months, so I wasn't looking too close. She had a nice body, but smallish tits. Again, I was so horny I didn't care what she looked like. She was being friendly and I hoped this would lead to sack time. It wasn't like I hadn't had sex in ten years. In prison I fucked and got sucked by my share of sissy boys. A mouth is a mouth, and a hole is a hole right?

A few hours into the party I knew things weren't going to work out as I had hoped, at least job wise. The woman was another thing. She gave me her number and told me to call during the week. At least in that department things were looking up. I had told her I had been in prison for robbery and she hadn't run screaming. That was a good sign.

I called and she invited me over for dinner and a movie. I explained I didn't have any money and she told me she was fixing dinner and she had rented a DVD. So I went over and we had dinner. We talked before she popped in the movie. I noticed she kept the lights low, and her voice was kind of deep but who was I to worry about that. I just wanted a good fuck and was willing to overlook lots of stuff.

We sat on the couch and watched about five minutes of the movie. I had my arm around her shoulders. I pulled her close and started kissing her. Her lips were soft and warm. Her tongue found mine and we kissed with a passion I hadn't felt in a long time. I took my free hand and started to unbutton her top. She didn't stop me so I continued till it was all the way open. She wasn't wearing a bra so her tits and nipples were right there for the taking. I noticed she was maybe a small B cup or maybe even an A cup. I didn't matter; they felt good in my hands. I started rolling her nipple between my thumb and first finger. She started moaning and put her head on the back of the couch. I leaned down and started rolling her nipple around in my mouth. I took my tongue and wagged it up and down while I had her nipple in my mouth. This sent her crazy; she grabbed the back of my head and pulled it closer. I thought I was going to suffocate, she was holding me so tight to her.

Then I started to rub the inside of her thigh. I was working my way up to her crotch when she stopped me. She pulled her head off the back of the couch and said that she wanted that to wait for now. Then she pushed me back on the couch, undid my pants and pulled my hard cock out. She put those warm soft lips around it and proceeded to pretend it was a popsicle. She took the flat of her tongue and ran it up one side then down the other. She slowly started moving her hand up and down the shaft. Then she put the whole thing in her mouth. I don't care if a girl can take the whole thing in her mouth without gagging. As long as she can suck it and make me cum that is all I care about.

This girl could really give a blow job. She flicked her tongue around the head and then put her whole mouth around it and sucked. All the while she kept moving her hand up and down slowly. Since I was so horny it didn't take long to bring me to my orgasm. Watching her head bob up and down, watching my cock disappear into her mouth was just what I needed. When I started to cum she just put her mouth around the head and took all my cum in her mouth. As I was blowing my load she was swallowing as fast as she could. After I stopped twitching and pumping she took her mouth off my cock, looked up at me a smiled.

She asked if I had ever had a woman give a better blow job. I looked down and said that I had never had a better one. She sat up, leaned against my shoulder and we finished watching the movie.

Our dates went like that for a little while. Finally one night I laid her back on the couch and started licking up her legs from her feet. I was heading for her pussy. I wanted to taste it, feel it with my mouth and tongue. I wanted to fuck it as hard as I could. She didn't stop me till I got up close. Then she said she didn't want to pussy fuck, she said she liked it up the ass. That was so she could enjoy herself and not worry about getting pregnant. My already hard cock got so hard I thought it was going to burst.

She was wearing a thong and a short skirt. I started to take her thong off, but again she stopped me. She said she wanted to do it with her skirt on and if I wanted to fuck her I was going to have to push her thong to one side. By this time I was so hard I would have agreed to almost anything. Anyway it was kind of kinky.

I ran my tongue up to her little rosebud. I pushed her legs back and up so I could get into a good position. I figured that if I was going to stick my cock up there, I shouldn't have any qualms about sticking my tongue and fingers up there. As I stuck my tongue into her ass I could taste the musky flavor. She started moaning and bucking as I pushed two fingers into her ass. I had made the entrance so wet with saliva they just slipped right in.

She was on her back with her legs pushed up. I had stripped naked; when I started moving up her body and she felt how hard I was her eyes went wide. She told me to stop for just a moment. She got up, went into the bedroom and came out with a large tube of lube. I had forgotten all about that, it would have been kind of uncomfortable if we would have fucked with out it. I know I could have dribbled saliva down there, but it wouldn't work as well.

She got back on the couch and scooted under me, put her legs up so I could push them back and told me to continue. I took some lube and put it on my fingers and shaved some up in her ass. I took some time to make sure it was getting everywhere in her ass. I shoved my three fingers up as far as they would go. I thought about fisting her, but I wanted my cock in there as soon as I could get it there. So did she, she started whispering in my ear that she wanted me to shove it in and give her all of it.

Who am I to disappoint a woman? I did as I was told; I slipped the head of my cock into the entrance. Then I stopped, I wanted her ass to get used to me being there. After a little while I started sliding in and out. A little at first then as her ass stretched I went deeper and faster. Finally my balls were slapping her ass, and I was burying my cock all the way in. She was bucking and pitching under me. She was trying to push her ass further up my cock. As we fucked I leaned down and licked her nipples. She licked her finger tips and started playing with my nipples. I don't know about you, but my nipples are connected to my cock. All of the sudden I felt ready to blow my load. I pulled out and started stroking my cock. I started shooting cum like a fire hose. It splashed on her stomach, and tits. She started rubbing it all over herself; she said it made her skin soft.

About a week later I went over to her house for our dinner and movie. She was in the kitchen leaning against the counter. I walked up behind her and started kissing her neck. I stuck my tongue in her ear, she started moaning and grinding her ass against my cock.

As I kissed her neck I reached up and started playing with her nipples through her shirt. She started hiking up her skirt and pushing back against my cock. I dropped my pants and pulled her thong aside. I stuck a finger up her ass and found it already lubed. I didn't waste any time. My cock was rock hard and I was ready to go. I slipped my cock into the entrance of her ass. Good thing I was holding onto her hips. All of the sudden she shoved her ass back onto my cock. She sucked in a breath and said "oh, shit," through clenched teeth.

Then she bent over the counter, looked over her shoulder and said to fuck her hard. She said she needed it hard and rough. I started fucking her hard. The harder I fucked the more she liked it. Pretty soon we were fucking so hard I thought I was going to get bruises or maybe hurt my balls.

If her neighbors wondered if we were having sex before that, they had no doubt now. She was screaming and shouting for me to fuck her harder. As we fucked I started to reach down toward her pussy. I needed to feel her pussy and I wasn't going to let anything get in my way. I liked fucking her in the ass, but I really wanted her pussy now.

As I reached down I thought she would stop me. She didn't, she just kept pushing back and keeping rhythm with me. I reached down to her pussy. Surprise, surprise, she had the same equipment as I did! I was getting too close to my orgasm to care at that point. I just needed to keep pumping in and out as hard as I could. It didn't take long after that. I blew my load so hard I thought my legs were going to give out. It felt as if my cock was pumping for ten minutes, although I know it wasn't that long.

We just stood there for a minute, and then her ass started pushing my cock out. She turned around, went to the sink and got a dishrag and towel. She came over, knelt down and cleaned me off. Then she got up, rinsed the dishrag off and handed it and the towel to me. She smiled, turned and stuck her ass out and asked if I would be so kind as to clean her up. My cum was already leaking down her ass crack and leg. I was still in shock and the after affects of sex. So I cleaned her up. That is when it hit me! I was going to have to start thinking about "her" as a "him."

She stood there looking at me. She always kept her hair down around her face, now she pulled it back and looked at me. I realized she was talking to me. She said that when she saw me at the networking party she knew she had to have me. As I looked at her I became aware she looked like someone I really knew.

I told her I really didn't like being tricked. She asked if I liked the blow jobs and sex. What could I say, of course I did, after all a mouth is a mouth, and a hole is a hole. She looked at me and asked if I recognized her and to think of her with darker hair. As I looked it dawned on me who she/he was! I fell back into the chair behind me.

It was Anthony my brother! Anthony told me it was Toni now. He had realized he was happier like this than as a full man. He had had breast augmentation and some cosmetic surgery. I asked about mom and dad. He told me they kicked him out when they found out.

Then he said since I didn't have a place to live, why didn't I move in with him. He said that he knew it was me at the party, and he still had to feel my cock in his mouth and ass.

She told me we could share the bed and still have sex as much as we wanted. As she said this she got on her knees and put her warm soft lips around my already rock hard cock.

Hey I'm all for brotherly love. And a mouth is a mouth right?