- 23 days ago
- 14 min read
- 8,900 views
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 her nice ass shake in that skirt. We sit and sip our drinks. Dave says he missed us and brings up the conversation of the threesome again. He asks if we would be interested in having one since we are two beautiful women and he is a good looking guy. We laugh and say, “Let’s have one more drink before we decide”, and Dave quickly orders another round and slaps his card down.
As we finish our drinks, we agree this is going to happen and being the planning. Maggie and I are staying at the Hilton and Dave is at the Marriott next door. Dave and I have king suites and Maggie has a standard Queen. Since two are at the Hilton, we decide my room is best. We settle up at the bar and head out. Dave says he wants to run back and shower quickly and we reject that saying he can shower at my place, he accepts with a smile.
We all walk into the hotel and head to my room. In the elevator, I lean in and kiss Dave and then Maggie. Dave’s hand rubs both our asses while I kiss Maggie and it turns me on for sure. We get off the elevator and I open the app to unlock my door and are soon inside. I ask if anyone would like a drink and quickly pass out a beer for Dave, a while wine for Maggie and I have a red wine. Dave takes a sip and says, “Can I take that shower now?” And I point to the bathroom and he quickly disappears. I move over to the couch with Maggie and begin stroking her leg as I go in for a kiss. She smells fantastic and she reciprocates the kiss with passion. I pull her blouse off and undo her bra. Her C cups perk to attention and I suck on her nipple while kneading the other with my hand. I work south and pull her skirt off. I admire her leopard print tanga and pull it aside and giver a quick licking. She drives my head into her vulva loving the feeling before pulling me back up for a kiss.
I kiss her and she works my blouse off and undoes my bra. My silicon insert spilling out exposing my clean chest. She doesn’t notice as she sucks my nipple and unzips my skirt. I shimmy out of it and it slides off my garter and panties. She goes down on me and gets just below the garter when she sees I have a cock and not a pussy and she rubs me hard through my satin panties and I grow hard. She pulls me to the bed like a circus elephant through my panties and I playfully push her back onto the bed. I pull her tanga off and admire her nicely trimmed pussy. She leans up and pulls my panties down and my cock springs out. She grabs it and presses it against her hole. It doesn’t slide right in as she is not wet enough yet but she wants it bad and spits on her hand and rubs it against her opening and after a few pushes in and out, I have lubed her inner walls enough to work up a rhythm. I am standing on the side of the bed with Maggie’s legs spread apart and fucking her hole when Dave gets out of the shower. He is confused at first as he walks slowly over to us before he notices that I am fucking Maggie with my cock and he doesn’t say a word. Instead, he leans into Maggie and gives her a kiss before lowering to suck her hard nipples. Maggie’s rubbing Dave’s hair with one hand and rubbing her clit with the other. She cums quickly with the attention being giver her tight body and I pull out of her. She pushes Dave to the side and goes down on him sucking his freshly cleaned cock with intensity and massaging his man nuggets.
I go over to my suitcase and pull out my toys: Anal Jewel, Strap On and lube. I throw them on the bed and say, “These are all freshly cleaned if anyone is interested.” And Maggie points to the anal jewel and I lube it up and slowly press it into her butthole. The ruby jewel shining in the lights of the hotel room as she bobs up and down on Dave’s glorious rod, slurping and sucking.
I walk over to Dave who is standing and enjoying his blowjob and I give him a kiss. He reaches down and starts stroking my cock as we make out and I resume my stiff posture. Maggie comes up for a kiss and we all fall onto the bed. I insert rub Maggie’s clit while she jerks Dave off and Dave continue to jerk me off. All of us are worked up now and I grab the strap on and have Maggie put it on. As she does works to fit it comfortably on, I go down on Dave and rim his asshole while jerking him off. I insert a finger when it is lubed up and he moans in pleasure as I finger bang his balloon knot. I stop and motion for Maggie to come over and she follows with the stiff plastic cock bouncing as she struts over, she grabs it and jerks it a few times while I coat its shaft with lube. I angle it towards Dave butthole and grab the shaft and slowly drive it deeper into his ass. He moans in pleasure as 7 of the 9 inches disappear inside him and Maggie works a slow pace to ease Dave into it. I add lube periodically as I watch the plastic shaft slow down with friction from time to time.
I straddle Dave’s face and my cock is inches away from his mouth as I take him inside my mouth and start sucking him off. His clean cock stained by the red lipstick Maggie has left behind but it still tastes good and I take his 8 inches to the base and gag while fondling his enormous golf ball sized balls. Dave strokes my cock while playing with my ass and spits on his fingers to get them into my hole of stink. He buries them deep and I love the feeling of him banging against my prostrate. Pre-cum is dripping from my cock onto his face and he directs my man utter to his mouth to capture the translucent liquid streaming from my cock as he plays with my ass.
Maggie is tiring of fucking Dave and pulls out. I wipe the toy clean and Maggie climbs on the bed and I lower my ass onto Dave’s face as Maggie takes Dave’s cock and slides it easily into her still wet hole. She leans into me and we kiss and she starts stroking my cock as Dave devours my ass. I reach over and play with her clit as she rides Dave. She cums quickly and coats Dave’s cock.
Maggie slides him out of her and I jump off his face. My ass is soaked with Dave’s saliva and I grab the dildo and take it from the strap on. I lay at the edge of the bed and invite Dave to fuck my ass while I east Maggie out. Dave comes around and presses his stiff know against my spit soaked ass and he eases himself in. The spit providing a good lube as he works my ass over. I have Maggie climb on my face and I begin eating her out as she lowers her face to suck me off, reaching around to play with Dave’s balls as he baselines in my ass.
I take the cock and insert it into Maggie and rub her clit with a quickie circular motion and she has all 7 inches of me buried in her throat sucking it away. Moans and moans of pleasure increasing as the tightness of my ass squeezes Dave’s cock.
I feel Maggie erupt in another orgasm and he coating of cum leaks out of her and onto my hand and face. I feel Dave push a few hard thrusts and he is smacking my ass as he does, he tenses up and I feel the warm of his man sauce coat my inner walls and the ping of his knob against my prostrate causes me to erupt.
The extended erotic experience produces a batch of cum that is 2-3 times the normal amount and Maggie cannot keep all of it in her mouth and some of it leaks out and slides down my retreating shaft. She keeps as much as she can in her mouth and lets my cock flop out of her mouth as she stretched upward to kiss Dave. Dave enjoys the creamy and salty kiss Maggie offers him and they both get a good taste of me.
I feel cum leaking out of my ass and gently ease Maggie off of me and roll over. I take the plastic cock and prop onto all fours and insert it into me. It’s veiny indents pulling Dave’s cum out of me with each retreating pull. Maggie and Dave take turns lapping it up and Maggie rims me clean, or as clean as I can get since some of Dave’s load is no doubt in my large intestine. They gather up and spit Dave’s load into my mouth and his creamy goodness is a good way to end the pleasure filled two hours we have just spent.
We all jump into the shower and take turns cleaning each other off which leads to another round of orgasms and then we all fall asleep in the king sized bed. We wake at different hours and play a little more and are all into each other. I eat Maggie’s ass while Dave fucks her, I fuck Maggie’s ass while Dave fucks her. I get fucked by Maggie while fucking Dave. There was no way we didn’t try and all of us experienced extensive pleasure.
We could barely walk the next day when we went to work but agreed to meet up again that night.
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