- Transgender & Crossdressers
- Hotel Cum Sissy
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Click hereI was on a business trip in central Pennsylvania and decided to stop for the evening and get a hotel room before I continued on the early the next morning. I stopped at a hotel just off the exit of the state highway around 7:15 and checked into a room. I had noticed that there was a small bar open just off the lobby while checking in. I arrived at the room, and had decided that I would just stay in the room that night, beat off in the bed and get to sleep early. I had packed a pair of women's pink lace and satin pink panties in my suitcase just for this occasion. I put on my panties and climbed in bed but still couldn't relax and get comfortable after driving so far that day.
I decided that if I stopped down at the bar and had a few beers, that it would relax me enough to give myself a satisfying stoke job. I quickly put on a pair of jeans and a polo shirt and headed to the bar. At the bar were only about 5 people and only one large gentleman sitting at the bar watching the football game on TV. I sat a couple of stools from him and ordered a beer from the barmaid. After a few minutes the gentleman, Mike, started to carry on a conversation first about the game then about the area of town that we were in. He said that he had been travelling for business also and had been on the road for 8 days and was wondering if there were any bars around this town where he could meet some women. I told him that I was from out of state also and I had no idea where he could meet any women. I bought another drink and one for Mike too. A half hour into our conversation and the football game, the bar maid left the bar area and had not returned for about 20 minutes. I told Mike that I was going to head up to my room because I have an early start in the morning. Mike said that he still owed me a beer and that he had a six pack of cold beer up in his room and that I could stop by his room and have one more with him before I hit the sack. Mike's room was just down the hall from mine so I decided to stop for one beer and watch the end of the football game.
Mike opened the door, gave me a beer and turned the game on TV. We started talking and Mike brought up the topic of finding a women and then said that she didn't have to screw him, just a blowjob to empty his 8 day load would be all he would expect. After an awkward quiet spell, Mike turned to me and asked me if I ever sucked a dick. I was really caught off guard and just didn't say anything. After a long silent pause and then Mike shouted, I knew it! I told him that I didn't think that that was going to happen and left it at that. Mike began to talk about the situation that him and I were in, and that no one would ever know and that it wouldn't take that long, etc... He offered me another drink and went into the bathroom to get two beers. When he came back into the room, he was only wearing a tee shirt and tight cotton long legged underwear. He said that he was just getting comfortable and was doing a little advertising for himself. As he walked around the room in front of me I noticed that his cock was getting bigger and starting to move down his leg. After 10 minutes of talking, walking around the room in his underwear with a semi-hard on and the beer starting to loosen my morals, I decided that I would suck on his cock for him.
I stripped off my shirt and pants and got on my knees on the floor. I had completely forgotten that I was wearing my pink satin panties. Mike took off his shirt and underwear and immediately filled my mouth with his semi hard cock. Mike was a big guy, about 6 foot 3 inches and built like a football player. I am only 5 foot 6 inches and 150 pounds and was dwarfed by his as I knelt in front of him with a mouth full of cock. His cock wasn't that big, maybe 7 inches long, but it was very fat and I had to stretch my mouth open to fit it in. As I was sucking and licking his cock, he pulled it out of my mouth and told me to suck on his balls. I opened my mouth and swallowed one of his big, shaved balls and sucked it good. He layed his hard cock on my face as I suck his ball sack.
I was getting horny sucking on his big, fat balls, so I started to stroke my cock in my panties and soon got my cock nice and hard so it was popping out the top of my panties. Mike saw me stroking my cock and told me that I had better not make a mess on the floor of his room. He then pulled his balls out of my mouth and shoved that big fat cock deep into my mouth and buried it in the back of my throat. That made me so horny that I knew I was about to cum and didn't want to upset Mike, so I stood up and with Mike's cock in my left hand I jerked my cock with my right and shot my cum all over Mike's fat cock. After I had emptied my load on his cock and put my cock back into my pink panties, I knelt back down in front of him. I licked a small amount cum that was dripping off the head of his cock and then just stared at his cum covered fat cock. Mike called me a "cum sissy" and told me I better clean up the mess I just made. On his command, I opened my mouth and slowly filled my mouth and throat with that beautiful fat cummy cock. Mike was also aroused and began to shove his cock deeper and faster in my mouth. He stopped and asked me if I ever had my face fucked before. I shook my head no and he told me that I won't ever be able to answer that question with a no.
He grabbed the sides of my head with his massive hands and held my head still while he violently fucked my mouth for what seemed like 15 minutes. He then shoved his cock to the back of my throat and started to dump the 8 day load of cum he had told me about. The pumping of cum in my mouth was more that I could keep up with swallowing. I swallowed about 4 mouthfuls of hot cum and it still ran out of the sides of my mouth and down my chin like a used slut.
As a continued to try and clean up and swallow all the cum, Mike announced that he was going to take a shower and that I better be gone when he's done and then pulled his cock from my mouth and walked away. There I was, left in the middle of a strange hotel room, on my knees, wearing pink satin panties with cum dripping from my chin and soaking the front of my panties. That was wonderful....
I quickly put on my shirt and pants and carried my shoes and socks down the hall to my room. I stripped to my panties and hopped in bed and suddenly realized that it was only 8:45 PM. It was then that I realized that it only took me 1 hour and 30 minutes to transform from a businessman to become the drunk cum sissy cock sucker that Mike used that night.
- COMMENTS
Anonymousabout 2 months agoTo Kevin
I would love to know what happened that night in the hotel. Did you pick a guy up? Or go back to your room alone and dream of sucking a strangers long thick cock.
Hopefully you at least went to the bar in your sexy white stockings and panties.
Do you have any toys? Do you fuck your ass? Do you suck on dildos?
How kinky do you get, when you're on your own?
I've practiced and practiced now I am able to deep throat a 8" life like dildo with balls, it's pretty thick. I love when it makes me gag and tears run down my cheeks. I can now push past my gag reflex and shove it down my throat. But sadly I've never touched a real cock. Let me know what you did that night. Also let me know how kinky you get when you're alone.
[Hotel Sissy]
Anonymousabout 2 months agoTo Mike aka (Hotel Sissy)
I am not a salesman but I do travel for work across United Sates and Canada. I am a trainer for my company. I've been married 17 years and I'm 46 years old.
I do similar things when I'm in a hotel room or home alone. I'm in a hotel room right now watching porn and stroking myself in stockings, garter and panties all white.
I feel so slutty and dream of sucking a big cock or 2 or 3 lol. When I watch porn I imagine I'm the girl sucking all those big cocks.
My wife or anyone else has no idea that I have this kinky secret. Reading your comments and others on here, it's exciting to think of other kinky married family men doing the same kind of things as me.
I do love to edge and eat my cum. I'm not going to cum yet though. I think I will put on my jeans and a shirt and go down to the bar. I have not yet sat at a bar with panties and stockings on under my cloths. It must be so exciting. I fantasize about picking up men but I think I would be to scared. But who knows...my heart is beating out of my chest right now thinking of the possibility. Me sitting at the bar dressed all slutty just below my shirt and jeans. If I go that far, where do I stop? Like you said about the excitement, it's so addictive.
Maybe I will post again to give an update.
Kevin
Anonymous2 months agoTo the salesman that has been married 15 years, that responded to my ( Hotel Sissy) comment.
I am home alone tonight ( March 1st) My wife is out for a girls weekend away.
I am stroking my 7" cock that's nice and thick. I have been edging for over an hour thinking of you doing the same. It's nice to know I'm not the only straight normal family man that has a kinky side. I just took a finger and licked a nice big scoop of precum. It taste so good, I can get lots out when I edge so I stay horny and hungry for cum. I'm like you, when I'm horny and alone I just can't control myself I do kinker and kinker things. I feel guilty too but can't seem to stop once I start playing.
I love putting my feet over my head and have precum and eventually hot cum all over my face. I feel so slutty and naughty.
I just stopped typing for like 15min. I edged out a bunch of cum onto my face, I love the smell and taste. After I did that I went and put a pair of my wife's sexy pink panties on. I'm stroking in panties with warm cum on my lips, nose and cheek. Oh God, it smells so good! I am so close! I don't want to cum because the excitement will be over.
I'm also thinking of my wife getting fucked by some guy with a big cock. She is conservative and wouldn't do that, but I think that's why it turns me on. I have never tasted another man's cum or been with a guy. But lately I've been thinking about licking another guy's cum out of my wife's pussy.
Comment back if you read this.
I'm going to make myself cum now!
Signed Mike aka Hotel Sissy
Anonymous3 months ago[HOTEL SISSY] Everytime i go on bunsiness trips i try to meet someone to visit me in my room, i played out a secretary, maid, cat woman, hooters waitress, and play boy bunny, i love being dressed up , i have walked the halls all done up or in just womens leggings, and tee, but never had the confidence of sitting at the bar, its a fantasy for me to maybe during halloween go tot he bar dressed as a woman and see who has an interest..
Anonymous4 months agoTo HOTEL SISSY ( last comment)
I also travel for work and do similar things in my hotel room. I'm a salesman and the road gets lonely, so you need to spice things up.
I'm also married 15years. I have never had a " sissygasm" but do fuck my ass and stroke my cock till I cum. I also eat my cum fairly often as I edge.
I like my hot cum on my face. Of course the wife or no one knows any of this. I'm just a straight normal family man but seem to be doing kinker and kinker things. I've worn my wife's panties and jerked off a couple of times recently, and feel that dressing might be very exciting.
I feel guilty about this stuff but can't seem to stop once I'm horny...like now. I'm home alone for the afternoon...already leaking precut...it taste soon good!
Anonymous10 months agoHOTEL SISSY
I have sat at many a hotel bar in panties and stockings under my jeans. When I travel for work only a few times a year now, thats when I let my inner sissy out. I will buy panties and stocking In the city I'm visiting, then throw them out before going home to my wife of 25years. I bring a bit of weed and some toys, 8" dildo and smaller hard vibratory. I watch porn and don't touch my cock. Then turn all the lights out everywhere and jump in a hot shower. I smoke a bit and play with my ass. I imagine there are at least 4 hung guys in the room waiting for me. After a long hot relaxing shower and ass play. I dry off in the dark putting on baby powder and my wife's old baby doll with stockings. I say out loud to the imaginary men "I'm almost ready".
Then I walk out into the dark room and dance around sexy with my eyes closed. Thinking of the men watching me. I crawl onto the bed and wiggle my ass. I have the toys laid out and ready. Sucking the dildo and fucking my ass. I talk out loud " I want you all to fuck me, I'm your hotel sissy".
I let the weed and darkness fuel my fantasy. It all seems so real. I feel my sissygasm build. " oh yes fuck me"
I keep the rythem going. I'm on my side thinking of getting gangbanged.
"You're going to make me make cummies in my panties".
I feel it build and I keep going then I'm over the edge! My whole body tingles my limp cock fills my panties with cum. I keep fucking my ass, my panties pulled to the side. My orgasm lasts well over a min. Then I keep up the fucking, and it happens again! I tremble and shake making strange grunting sounds and almost black out. I have only had a multi sissygasm once but that's how it happened. That was 2 years ago, I'm going away on business next week.
I'm going to kiss my wife good bye and try to reproduce the entire scene.
Or better yet let another lonely businessman see my panties under my jeans and see where it leads.
Respond to this ( HOTEL SISSY) if you do similar kinky things When traveling or home alone when the wifes away.
Anonymousover 1 year agoOh, to walk the hall of a hotel smelling of cum, and some drying on chin. Been there, done that. One time a chamber maid stopped me and said here, let me help you and gave me a couple warm wet ones from her cart, as i left she said see you tomorrow; as start to long freindship.
Anonymousover 2 years agoHad it happen to me, at the doubletree at sea-tac in 2004. I was at the bar having a drink. Just me and one other business traveler and the bartender. At the time I wore panties 24/7. The guy saw my pink panties above my jeans. Leaned over and complimented me on them and asked if I wore anything else to which I replied yes, I dress head to toe often. He asked if I liked cock and again I said yes. Was a fun night before flying home to the wife!
Anonymousalmost 10 years agoThe story sounded like fun. My wife knew I wanted to suck cock and after she started menopause and her sex drive waned, told me once she didn't care if I fulfilled my fantasy. Her only stipulation was that the first time, she had to be there.
I called up my friend Mike and invited him over for some drinks. One thing led to another and she helped me out by daring him to let me suck his cock. He was single and didn't date so we hoped he was safe. My wife told me that if he played his cards right, he wouldn't have to date!
Soon enough he was drunk enough to let me fish his cock out. As drunk as he was, he must have been horny as hell, it was half hard before I touched it. So, there I knelt on my knees, with my friend of 45 years and my wife looking down at me when I took his cock into my mouth. I fear they heard me moan when I tasted it. Other than a little piss taste, it tasted masculine. I sucked the head for a while, treating it like a sucker. Then I started jacking on the shaft. It didn't take long and we could tell he was about to blow (pun intended). My first time sucking a cock and I was making it cum in less than 120 seconds!
He told us later, he hadn't cum in over 2 weeks. And when it started, it was amazing. His cock head swelled and I heard him take a big breath and hold it, then thick gobs of sperm started pouring into my mouth. Thick at first, then long long squirts following. Then big gobs again. I never lost a drop. I sucked and swallowed, sucked and swallowed. When Mike had finished in my mouth I continued to kneel while holding his cock in my mouth. I watched as he reached over, took his beer and a few drinks, then stood and looked down at me again.
When I stood, it was kind of awkward. I had pulled my cock from my pants and when I stood it stuck out hard as a rock. My wife asked Mike if he liked that and he said, truthfully it was the best head he'd ever gotten. She asked me if I like doing what I'd long fantasized about and I answered yes, it was incredible. As they both stared at my cock (I'm the larger of the two) she told me she didn't care if I did it as much as I liked, just with no one but Mike. Then she told Mike that he couldn't be out screwing around, she didn't want any diseases in our house, but if he wanted, he could come over for a blowjob whenever he needed to cum. He laughed a little and said probably not that often, he liked to cum a quite a few times.
I let him know that I'd suck him whenever he wanted, whether it was once a day or 5 times a day, I wanted to be the one to make him cum. Mike was slightly amazed and told me if I was serious, he could stand another one right there. Looking down I saw he was hard as a rock again and it was pointing straight up! This time when I went to my knees, I started pulling on my own dick, but waited for his orgasm. When he stiffened and started to grunt, I waited until he started to squirt before letting my own go. You can't imagine the excitement of taking in cum on one end and letting it fly out from the other.
I suck him now sometimes once a day, occasionally as much as a half dozen times per day. On football sunday he comes over and I suck all day as we watch the game. I like it when he doesn't come over for a few days before the big game day so that I can get more volume of sperm in my mouth and more often. I like tasting the really big loads with the thickest of sperm. I especially enjoy being a cock sucker. Not for anyone, just for Mike. I like making him feel good with my mouth and earning my reward.
michelle6969over 10 years agoI was wearing a pink suspender belt and G-string with black stockings under my trousers as I sat on a barstool watching a young singer, nearly wearing clothes, on the box. The bar was crowded and I kept sliding off the stool which I didn't notice had opened a gap above the waistband. Suddenly a hand slid down inside it and groped my arse, then hooked a finger through the string and started working it up and down. This forced my balls out, one each side of the narrow part of the pouch and I started to get a hard on. My room key was on the bar and was picked up by a well manicured black hand as "to your room now" a masculine voice whispered in my ear, I was walked, with the hand still fondling my cheeks, back to and into my room, where He turned me towards him and holding the back of my head kissed me roughly. I don't normally kiss men but he was so overwhelming that I tilted my head back and kissed him back. He then stripped me till I only had on my fem gear and pushed me to my knees. I knew what to do and got his cock out, about 7" semi-hard, and took it into my mouth. I bobed and slurped as he grew much harder and at least 2" longer wanting to feel his cum in my mouth as I struggled to take his girth. He had other ideas and threw me onto the bed, pushed two pillows under my arse and my legs over his shoulder. At this point I came and as he was pushing his baseball bat against my virgin hole I Frantically smeared his weapon with my cum and managed to finger some into my tight little ring. He forced himself into me which was painful at first, but got duller as he fucked his whole length inside me. Starting with a short stroke he soon loosened me up and was giving me a tip to balls fucking. I don't know how long he took riding me, but it was too short as far as I was concerned. I was groaning and leaking more cum and enjoying loosing my cherry till he emptied his load into me. He fucked me four more times that night and I booked in for a further three nights, leaving with a much looser hole!
