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A threesome with my GF and Ladyboy

I’ve been with my girlfriend, Karen, for about four years now and my eye has only wondered twice. I’ve never cheated on her but she knows I have always been keen on seeing her getting fucked by a chick while I watch. There’s something about watching a girl getting fucked by another girl with a strap-on, or better yet an Asian ladyboy doing my girlfriend, that gets my cock extra hard very fast. My girlfriend had been interested in experimenting with girls for a couple of years now but we’d never really found a girl we both thought was hot enough or actually willing to play along. Also, we didn’t know any ladyboys so that fantasy was still sitting in limbo.
That was until my girlfriend started her new job and met her latest close friend, Jamie. Jamie was a bubbly, beautiful, toned Asian stunner with a firm looking ass and bouncy breasts I’d sometimes fantasized burying my face between. She had sultry thick eyelashes, blue eyes and lips you know would suck a cock damn hard! Karen had gotten to know Jamie pretty well at work and started inviting her over to our house to work on ‘work projects’ and generally just spend more time together. I thought it was a great chance to maybe get some girl-on-girl action some time so I approached Karen about it. She said she’d casually mentioned it to Jamie and the cute little Asian girl didn’t seem disgusted at all. In fact, Jamie had mentioned she had always wanted to try the same thing and didn’t mind if a guy wanted to watch.
So the following week, when we all had a day off work, we invited Jamie over. She arrived in her skimpy short denim skirt and a tight sleeveless shirt that I could almost make out her nipples in. We sat and had some lunch and a couple of glasses of wine in the lounge, just to relax the mood a little. I thought I’d break the ice by saying “so what do you think about you girls having a little kissing action?”
I got a smile from both of them and a chuckle from Karen.
”Wow, you really know how to move things along don’t you,” she said, turning to Jamie and smiling. Karen leaned in and gave Jamie a closed mouth kiss on the lips. My eyes were fucking wide open by this stage – finally this just might happen! Jamie lifted up her hand and curved it around Karen’s jaw, opening her mouth and licking Karen’s lips with her tongue. Karen brushed her hand over Jamie’s perky boob and squeezed it. All my Christmases had come at once!
My cock was hard as the girls started to undress each other from the top down. Karen’s panties were on the floor and Jamie was lapping into her pussy like she hadn’t eaten all day. Karen was obviously enjoying it because her moans were getting loud and her tits were getting pink from all the squeezing she was giving them. Jamie was bent over in front of me and I could see a bulge in her pants. I had a feeling this could get interesting. The idea of having an Asian ladyboy in my house sounded even better than two girls – this would be like Karen letting me watch her almost have a threesome! Better yet, this would be Karen getting fucked by a hot chick with a permanent strap-on! I couldn’t take my eyes off that growing bulge until I saw Karen grip the couch. She was definitely taking to Jamie’s tongue!
Jamie pulled herself up from Karen’s dripping, throbbing warm pussy and turned to face me. She took off her bra and showed me her perky breasts, then grabbed my hands and made me grope them. They felt like a twenty year old’s tits, deliciously firm. Jamie turned around to face Karen and said “I have a big surprise and I hope you don’t mind,” and pulled down her pants to expose her big cock.
“Holy shit!” I exclaimed, getting turned on even more now that my suspicions were confirmed.
Karen looked at Jamie, smiling, and said, “Well I wasn’t expecting that.” Karen looked even happier. I know she likes cock and she was nervous about going down on another girl so we both knew a dick would be much more comfortable.
Karen got down on her knees, grabbed Jamie’s big ladyboy cock and started giving her a blowjob. It was a mega turn-on seeing my woman giving this stunning kathoey a blowjob. My cock was almost as hard as Jamie’s! I watched her twist her ladyboy nipples on her big, firm tits while my girlfriend went to town on her cock. Karen’s cocksucking tricks seemed to work well on Jamie too because her leg seemed to shake a little and she had to pull Karen off.
Without a second thought, the Asian ladyboy spun Karen around and had her down on all fours, ready for cock. I had my cock out of my pants and was pounding it fast. Jamie was rimming my girlfriend’s ass and Karen loved it! I was looking forward to the climax of this wild Asian ladyboy sex session and hoped her cock would end up in either Karen’s ass or her pussy.
I watched as the ravishing Asian shemale slowly pushed her Asian shemale cock into my girlfriend’s pussy.
“Oh fuck yeah” I said under my breath as she pumped the fuck out of my bent over girlfriend. Karen was rotating her fingers around her clit fast as the ladyboy stunner kept fucking her with her massive, ‘organic’ strap-on cock. Jamie had Karen by her shoulders, had her back arched and was grabbing at her tits while she doggy styled her. Jamie got faster with her thrusts and dug in deeper with her eight inch ladyboy dick.
Karen started to scream like I’ve heard her many times before and I saw her go stiff and then shake a little as she yelled out “I’m CUMMING!”
All my wildest fantasies with a ladyboy were coming true! I just watched my girlfriend cum from a stunning Asian shemale ramming her pussy with her organic strap-on!
I felt my cum starting to make its way up my cock shaft. I got out of my chair and knelt down in front of Karen’s face. She was now back on all fours and looking quite relaxed and breathing heavily, still taking cock from the racy Thai ladyboy. My cum exploded all over her face and squirted into her hair. She opened her mouth and started bobbing her head up and down slowly, taking the last squirts of cum in her mouth and cleaning it up with her tongue.
As I collapsed on the floor, my dick exhausted after such a ride, I saw Jamie pull out of Karen’s throbbing pussy and watched her ladyboy cum squirt up and down Karen’s back. Jamie kept thrusting slightly back and forward, knocking her balls against Karen’s cum dribbled ass.
“That…” I was exhausted and couldn’t get my words out properly, “was fucking… awesome!” We sat there for a while until we all burst out laughing.
“I would so do that again,” Karen said, reminiscing about the wild Asian ladyboy sex session that just surprisingly popped up.

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Posted on Friday, January 14th, 2011 at 11:47 pm and is filed under Stories.