Fetish Fun

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Fetish found

I am an average guy with above average sexual desires. I typically travel a lot for business which allows me to play out many different desires. I often cheat on my significant other when out of town and it could be with just about anyone.

When traveling, I only wear panties and the feel of satin on my balls and cock provides a day long eroticism that builds as time goes on. If you have never worn panties, I highly recommend you try them. You are missing out on something.

Being of average build and male, I need to do a few things to dress the part of a woman. The first is a full body wax: except a small pubic area but I have them shape that area very nicely. Next, you need to have the right clothes. I wear a bra and have nice silicone inserts that give me a nice A- to B+ cup appearance and just putting that on makes you feel more feminine. I match my panties and bra all the time and sometimes add a garter belt which is so damn hot! I love the way it looks when women wear garters, it completes my outfit as well! A nice skirt is good as well, I like pencil skirts as they are able to hide my bulge and make my disguise more real. I also have to wear makeup which took some practice to get it right but not too much as I do not have much facial hair and I wear a wig which is custom made and throws my hair into a pony tail. I accessorize with hoop earrings and a few rings and bracelets. I wear short heels as I am not good with anything over a 4” heel (working on it but have no idea how women do it!). I always wear stockings, often with a small pattern like polka dots or a line up the back. I then spray some perfume on my wrists and one blast up my skirt, just in case.

I also like to bring along a variety of toys: anal jewel, strap on with detachable dildo, and of course a good lube.

I love to head out when I am traveling dressed as a woman. It is a liberating experience and one that is very fun. The anonymity of a different city combined with dressing as a woman releases a sexual energy that I cannot explain. It transforms me to not only looking like a woman but actually feeling like a woman. Like I said, I head out to a bar and at first the mannerisms of a woman needed to be worked on but not I have had a lot of practice and do need to focus a little so that I don’t slip into masculine mannerisms but it is almost second nature at this point.

On this particular night, I sit at the semi crowded bar and can see that a few eyes turned when I sauntered in wearing my black pencil skirt, gray silk blouse, black panty hose and red 4” pumps. I sit at the bar and I order a Bullit Rye Old Fashioned and take in the sights. I have a woman on my right and a guy on my left-both business professionals judging from their attire. The woman chats me up first commenting on my diamond tennis bracelet. She introduces herself as Maggie and I reply that my name is Sydney, my feminine name.

I comment on her outfit, a nice Burberry number and she is cute. We chat back and forth and have a few drinks before Dave chimes in on the other side after eavesdropping on our conversation about blowjobs. Maggie hates when they pull out and shoot the load on her face. I don’t mind it and we ask Dave if he has an opinion he would like to share. He says its a man’s duty to warn the woman they are cumming and prefers to establish that ground rule up front so as to avoid any confusion or disappointment. We all laugh at that but think it is a good rule of thumb. Intrigued by the conversation and daring it to go a step further, Dave asks about anal. Maggie says she has never had anal but does enjoy ass play with fingers. I proudly announce that I like it and enjoy it so long as the guy is respectful of it and doesn’t pound at me like a jackhammer. Dave announces he likes ass play and has used a jewel before. Intriguing I note to myself.

We move the conversation to favorite positions and Maggie states she likes the backward cowboy as penis seems to hit her G-Spot better in that position. I state I like doggie and Dave chimes in that he is game for any position so long as he is getting laid. Again, we laugh and decide to throw a shot of whisky down before another round is ordered. Dave throws his corporate card on the bar and says, “My round!” And we all cheers before downing the shot.

Dave shifts the conversation to threesomes, pressing his luck this early but I guess we are tipsy enough to dive in. Maggie says she has had a threesome before. It was in college and it was with her two sorority sisters, they had a few dildos and played with each other one night after too many Screwdrivers. She enjoyed it a bit but really liked a good dicking. I said that I had not (lying) but was interested possible if I found the right people. I would be open to lesbian or straight combinations so long as it was respectful for all parties. Dave said he had one in his early 20’s while vacationing on the Cape. It was fun but he found himself paying more attention to one of the women that that other and the other woman got mad so it wasn't a “good” experience.

I order another round and place it on my corporate card. Maggie and Dave both say thanks and I can see their eyes are glossed over as a solid buzz has settled in. Maggie and I excuse ourselves to use the ladies room and when we finish with our stall duties, we head to the mirror and adjust our hair and makeup. Maggie says, “Dave seems interested in a threesome. Would you consider?” As I fix my lipstick, I say, “I think I could be interested, you?”, and Maggie responds, “Yeah, he’s kind of cute and you are super hot so it could be a fun way to spend a few hours tonight.” “Okay”, I say and continue, “but lets play a little hard to get. Dave will surely be into it and maybe he will get a us a few more drinks if we tease it enough...” “Wounds like a plan”, Maggie says.

We head back and I am behind Maggie looking at

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Written by shyguy654
Cargado March 29, 2021
Notes Three way with Surprises at every turn
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