Monthly Archives: October 2008

Gilberts roomate catches him while he gives himself a tease sucking on a dildo

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strapon-sissy22

Gilbert was sure to pic a lesbian as a roomate. They had just started the first semester and when Stephana was away at class Gilbert would play. Gilbert was a first class grade A sissy boy ! He loved strapons and when his roomate was out would dress up in her panties and lingerie. What a turn on it was for him. Until he got caught. She walked in the door and he was going at it up his ass on the couch. He didn’t even know she was there so she decided to just peek around the corner and watch him pleasure himself. Thats when she started masterbating too. Stephana didn’t want to embarass Gilbert but something had to be done about this. She decided to take matters into her own hands.

She walked right up to Gilbert and demanded he hand over the strapon. He didn’t know what to say and the fact he was embarassed turned something on in Stephana. She finally going to fuck a man with a strapon! She was used to fucking her lesbian friends but this was new territory. She it on and grabbed Gliberts heels with both hands, threw them in the air and proceeded to fuck his bitch ass ! He was so pretty wearing makeup it turned on Stephana even harder as she pumped his tight little ass. She new what it felt like to get fucked hard and delivered a good fucking to Gilbert! The harder she fucked him she could feel the dildo rubbing againts her clit and while she was jacking him off she started to come. Gilbert could see she was having an orgasm and thats when he shot his load into his own face. “Mmmmmmm”, he was so pleased. Stephana was satisfied also and bent down to kiss him. They swapped Gilberts cum while they french kissed. Their friendship was never the same. If you didn’t catch the movies from the link above you should see the screencaps !

The crossdressing sissification of their friend Danny

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shemalesissification com carla and shakira

Yeah Danny had some shemale friends. He would come over and hang out while they all took dirty sex photos and drank vodka. It didn’t take long to make him the sissy bitch boy everybody already knew he was. Especially when he would show up in Makeup and lipstick. Danny got his lipstick all over Shakira. They don’t call her Shakira for nothing. Maybe it’s the booty. I don’t know. Anyway, as you can see from these photos everyone had a great time in the Sissification of Danny the little sissy suck toy ! Who needs a strapon when your two best girlfriends have cocks ! Check out all the movies they have updated every week to see the transformation of this guy into a first glass grade A bitch boy !

Subrina lets the asswhore sissy suck her strapon !

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So we invited Nathan over for cocktails. I had some of the ladies over from College. A lot of debutants and misguided law school ladies that were looking for fun. The thing about sissy porn is there is always a well availability of female talent wanting to use and humiliate the bitch boys. Everyone knew what was going on at the party but Nathan. He did some work in the office sometimes and expressed interest in doing some modeling work. We all knew he was a sissyboy and we would never let him work on a real porn shoot. I told him to stop on by the party to meet some ladies and we could work something out possibly on an intern type basis.

What a sucker. Yeah, he was a sucker alright. We thought he had a pretty mouth and when Subrina showed up she expressed an interest in Nathan right away. “C’mere” she told him. The other ladies just watched as Subrina applied lipstick to this eager young pleeb. He didn’t even fight it so Samantha came over and put a wig on him. I told him if he wanted to do porn with the big boys he was going to have to be these girls sissy fuck toy first. You gotta pay to play. He agreed and they proceeded to dress him up more. We all got real friendly and he was mingling with the ladies quite well sitting on the couch. After a little wine and cheese Subrina came out of the bathroom with a strapon dildo. Nathans eyes lit up. “Open your mouth”. At first Nathan was scared but all the ladies assured him it was okay. “Start sucking I said” , Subrina was very forcefull now and he immediately did what he was told. I decided to just start taking some sissy photos and bingo. We had a new sissy to party with. I hope he wasn’t expecting to get paid or anything.