The last time I gave a man a blowjob was only the second time I’ve ever done it. It was five years ago. To this day, its still one of the hottest stories I have. I was driven to post it when I drove by the hotel we met at today. I drove by the hotel and instantly became rock hard thinking about what he did to me. Hope you enjoy ;)
We met on Craigslist. He responded to an ad that I put up. The subject alone was enough to picque my interest: “Hello Slut”. He explained that he was here on business and would love to shove his cock in my mouth while I was dressed in some slutty lingerie.
I found myself replying, making plans with him. He was out to dinner with coworkers and would e-mail me when he was back in his room. I heard back from him, we exchanged phone numbers and he texted me to tell me where he was staying and in what room he was in. He also told me that my name is Tina.
What the hell am I going to do? I’ve given one man one blowjob, once. Here I am, putting on my favorite lingerie from Fredericks of Hollywood. A black satin bra, g-string and garter belt with pink trim. The cups in the bra are split and can be tied up with a piece of pink satin. To complete the outfit, a pair of black thigh highs with a pink seam. I put on my lingerie and, to ensure discretion, put on a pair of jeans, a baseball jersey and hoodie. Enough padding to make sure nobody will be able to see my bra lines. It’s August and hot as hell. I nervously walk out of my apartment, feeling as though everyone can see what I’m wearing under my clothes and get into my car.
I’m simultaneously nervous and excited as I navigate my way to the hotel. I’ve got butterflies in my stomach. I’m in a trance, so focused on the feeling of the lingerie that I’m wearing that I didn’t even notice that I’m already at the hotel.
I park by the side of the hotel. I’d feel like a hooker walking through the lobby, feeling everybody stare at me, again, like they can see what I’m wearing underneath my clothes. A side entrance! This is my way in. Nobody will see me.
Except for the nice family that is walking in the side door in front of me. I realize that I would have needed a key card to open the side door, so I start to jog to catch up to them. They hold the door for me. “Thank you” I say politely, in a voice higher than I would have expected to hear myself say it in. The naughty lingerie I’m wearing and the cock I’m about to suck clearly have me thinking about being a woman.
I begin to walk upstairs to the second floor. I’m surprised to find his room right across from the stairwell. I’m already here. The butterflies in my stomach is mixing with fear and anxiety. It’s now or never.
I nervously knock lightly at the door. **Knock, knock**. It’s too late now. I can’t run. He is expecting me, I am here and he has assured me that, while he is on the dominant side, if I freak out and get nervous and need to stop, that it is okay.
He opens the door. A tall, decently built man in his late 40’s opens the door. He’s cute! “Are you my little slut?” he says quietly? “I am”, I reply in a meek voice, again, in a higher pitch than I expected.
He invites me in. We’re both fully dressed. He’s very nice, charming. It’s relaxing me a little bit. We talk about ourselves a little bit. He’s in a white t shirt and gym shorts, freshly showered. I take off my hoodie, and am now in my baseball jersey and jeans.
He finally breaks the ice: “Can I see your outfit?”
I nervously fumble with the buttons on my jersey. I’m standing there in front of him in my bra and jeans. He begins to admire me, running his hands across my chest, untying the lace up cup so that my nipples spill out. He gently tugs at my nipples.
“…can I take my pants off, Daddy?” It just slipped out. I didn’t mean to call him Daddy, it just happened. I dated a girl in high school who liked to call me Daddy and it drove me wild. I guess since then I’ve associated calling someone Daddy as a sign of subservience. If he disliked it, he didn’t let me know and told me take them off. I remove my shoes and then my jeans. I’m now standing in front of a total stranger in a bra, g string, garter belt and thigh highs, ready to do whatever he asks me to.
He tells me to bend over. He rubs my ass gently, then smacks it lightly. He then takes a seat in the standard issue hotel desk chair. He’s still in his tshirt and shorts. I’m in my lingerie, on my knees in front of him. We’re just chatting like a couple of buddies. I don’t even remember about what, it wasn’t about what was about to happen.
Before I know it, I have moved my head in between his legs and start to nibble on his cock through his shorts. It’s flaccid at this point, and still feels large. My hands are behind my back, like they’re tied up.
He lets me slobber all over his shorts for a few minutes until he finally stands up. He removes his shorts and I’m staring at his cock. It must be 8 inches long and thick. I’m breathless. My cock is thin and maybe 5 inches, rock hard. This is a monster. And I have no idea what I’m going to do with it.
I start to kiss it. Then I start to lick the shaft. Finally, I open my mouth as wide as I can and I take him in my mouth. Nobody told me I should try breathing out my nose (I didn’t learn that at all day) and I start gagging hard on his cock.
He’s understanding, but firm and insistent. “SUCK”, he says. I do as he tells me to. Sucking and gagging, sucking and gagging. Then he tells me to suck his balls. He wants both of them in my mouth. I begin by licking them, lapping at them like a dog drinking water. “I didn’t say lick, I said suck, slut”. I open my mouth and put both balls in my mouth, swirling my tongue around them while they’re in my mouth.
He decides to give me a break to catch my breath. He pulls his balls out of my mouth and starts to slap his heavy cock across my face. This was a special request of mine. I wanted to be cock slapped. The wave of humiliation I felt as another man slapped me in the face with his (much larger than mine) cock while I was dressed in slutty lingerie was intoxicating. My hands are still behind my back, like a good, obedient little girl.
He then commands me lean against the side of the bed, with my back against the side of the bed. I crawl to the bed and remain on my knees up against the side of the bed. My feet are under the bed, hands behind my back and I’m waiting to see what he’s going to do next. He slaps my face a couple of times (more stinging humiliation) and then starts to fuck my mouth again. Gagging, sucking, drooling and slobbering. I look (and feel) like one of those girls from a “gagging blowjob” video, with drool running down my face, making all sorts of gurgling noises while I suck this man off.
He pulls out and commands me to jerk off. I’m still on my knees, stroking my cock while he’s stroking his cock in front of me. Once I’ve worked myself up, I start to beg “Can I cum Daddy? I want to cum”. He says I can only if I lick it up. I cum into my hand. Like a good girl, I lick it off and swallow every last drop.
He then makes me start licking his balls again. He’s going to finish himself off with his hands. I was too nervous to agree to swallowing him, and the only other time I sucked a cock, I insisted on a facial. He was going to mark me as his and cum all over my face. Just the way I wanted it.
I’m licking his balls, he’s stroking his cock. Finally, he grabs the back of my head with his hand, positions my face right where he wants it and begins to coat my face in streams of thick, warm cum.
Once we’re done, I go to the bathroom. I can’t stand the look of myself in the mirror. Garters, thigh highs, g string, bra and a huge load on my face. I’m quite the slut, and now that I have also cum, I feel every bit the slut that he knows I am.
I wash my face and take off my bra. I keep the bottoms on because I’m not going to have the room to cram them in my pockets on the way out of his room. I threw the bra on the bed while I got dressed. I stuck around, like I said, he was charming. We kept chatting, like a couple of old buddies, I just happen to be wearing lingerie under my jeans and just cleaned my drool and his cum off my face after sucking on him for a half an hour.
I put the baseball jersey back on and then the hoodie. We talk about his family, my family. The relationship that I had just come out of. That I’ve never really done this before. Like I said, one other guy, one blowjob. That was truly a blow and go. This is supposed to be awkward, and it kind of is, but it’s not as awkward as I would have expected. After about 15 minutes of chit chat, I decide its time for me to go.
“Don’t forget your bra, otherwise I’ll have to take it home as a souveneir and my wife wouldn’t like it if she found it,” he says. I made sure I took the bra and crammed it in the pocket of my hoodie. I think he was a little disappointed and that he did want a souveneir. If it wasn’t my favorite bra, I would’ve let him take it.
I walk out his door, and back to the stairwell I came from. I felt a little more empowered as I walked back to my car. A little more self assured in what I had just done. A little more confident. As I came out of the stairwell, I pulled my bra strap out of the pocket of the hoodie a little bit and let it hang out, as a way of saying “I don’t care who sees”. Nobody saw. I walked out of the stairwell, out the side door and back into my car without seeing a soul.
Once I got home, I showered and collected my thoughts and I sent him an email. A thoughtful email. Thanking him for being firm when I needed it, for being sweet and charming when I needed it and for being filthy and humiliating because I wanted it. Like any good girl, I thanked him, asked him to get in touch with me should he ever be in town again and signed it Tina.
Source: reddit.com/r/gonewildstories/comments/6bqh8f/mm_cross_dressers_story_of_visiting_a_dominant
Great story. You might wanna x-post on /r/cdstoriesgonewild