I replied, “I’m telling you that this is the only other experience I’ve ever had with another man in my life, and so far, you’re way more romantic than he ever was.”
He said, “I know I told you that I was dominant on the message board, and I am, but that only means that I like to provide comfort, pleasure, and strength to the people I hook up with. I’ve hooked up with a lot of girls, but I haven’t hooked up with many more guys than you have, to be honest. I’ve never hooked up with a crossdresser in my life. I always thought they were sexy, but just never had the chance, I guess. What got you into crossdressing to begin with?”
I didn’t really know how to answer that question. I mean, it’s obvious that women’s clothes are so much better than men’s clothes, but for me, it went beyond the luxurious fabrics and cute dresses. I answered as best I could.
“Well, I wish it were as simple as enjoying dressing up, but it isn’t, really.”
I nervously finished my drink, so he got up to get me another one, and asked me to continue talking.
“I guess I’ve always quietly felt like some kind of genetic mistake was made when I was being put together in the womb. Growing up, I always felt like I was different on the outside from how the entire rest of my being felt on the inside. Sure, the clothes were arousing to me as a younger person, because I knew what I was doing was considered taboo, but honestly, the only times I really ever felt like I was ever being honest with myself were when I was dressed up and being a girl.”
He came back in with my drink, and noticed I was visibly anxious and vulnerable from talking honestly with him. He acted quickly.
“Relax, baby,” he said, “you’re safe with me. Nothing can hurt you. Understand?”
He handed me the drink and moved in closer to me again when he sat down. Our knees were touching, and he put his arm around my nervously shaking shoulders, pulling me in closer to his body. I took a big sip of my Cosmo, then set it on the table, and put my head on his shoulders. This felt really good and very normal. His presence had a calming effect on me. I continued,
“So, for me, it’s not just a fetish, it’s my desperate attempt to claim some of the real me away from what society deems who and what is or isn’t male or female. Does that make sense to you at all? Or is it TMI?”
He snickered when I said that, kissed the top of my head, and said, “If I’m being totally honest, I don’t fully understand someone being confused about their gender, but I totally respect it, and find your earnest desire to be a woman fascinating, and I think it’s totally hot.”
As my head rested on his chiseled shoulder, I glanced down his entire body with my eyes, and saw his cock was very hard, and that his boxers could barely contain it. I sighed longingly, and he subtly laughed under his breath, then made his cock jump around in his boxers, telling me that it was saying hello to me, which made us both laugh, and he gently pulled me in tighter and closer to him.
He was running his hand up and down my back, and sticking it between my babydoll nightie and bra, running it all the way down to the waistband of my panties, and gently drifting his fingers down to the top of my ass crack. It was so arousing that I was breathing heavier with each rub he gave me.
“I know this much: I want you to feel comfortable and safe with me,” he said in a low tone, practically a whisper.
I replied, “I do, baby. I’m nervous, but in a good way. I don’t know if it’s possible that I could feel any better than I do right now.”
He replied, “I’m willing to bet that you could feel better, and that you will feel better soon.”
That really turned me on, and I turned my head into his chest, giving a soft, wet kiss to his moderately hairy pecs, which made his breathing intensify.
“Would you mind if I kissed you?” he said to me, as he gripped my shoulders tightly.
I replied, “I thought you would never ask,” and smiled at him as I moved my lips closer to his, where we locked our mouths together in unison.
He was a tremendous kisser, gentle but forceful, with lots of tongue, but he knew how to use it. We were both breathing heavy as we made out uninhibited. I don’t know what came over me, but instinctually I fully turned my body and straddled him, with my legs spread, and resting my silky ass right on his throbbing cock.
The kissing became more intense, and I naturally started grinding up and down on his crotch. He lifted up my babydoll and grabbed two full hands of my ass cheeks as we were slobbering all over each other’s faces. It was at that moment that he sweetly, but forcefully slapped my ass through my panties. I gasped organically, and was as turned on as I’ve ever been in my life, then let out an approving whimper as we kept making out, and it prompted him to do it again, which made me whimper in ecstasy again.
“Shall we take this to the bedroom?” he asked, as we kept on kissing and grinding on each other.
I smiled at him in between kisses, and again said, “I thought you would never ask.”
He laughed, and slapped my ass again before saying, “Go make yourself comfortable in my bed, sweetie. There are toys and party favors on the nightstand. I’m going to refresh our drinks, make sure the door is locked, and use the bathroom.”
I grabbed my bag out of the bathroom to get my lipstick, and walked like a giddy sissy girl to his bedroom. He had candles lit on the bannister and on the window sills, and soft, sweet soul music playing at a low volume on the stereo in his room. Daddy had game.
I looked in the mirror and applied more sparkly pink lip gloss to my pouty lips before getting into his bed. I laid down on top the sheets, and wriggled around, trying to find the perfect pose for him to see as he entered the room. I glanced over at his nightstand, and saw rubbers, cherry flavored lube, and a fresh bottle of poppers. Yeah, like I said, daddy had game.
I stacked two pillows on top of one another and laid back on them. I spread my legs, took 2 fingertip sized dollops of lube, and made my way down to my sissy pussy to get it nice and wet. I pulled my panties to the side, and slowly massaged each finger into my hole, getting it nice and moist. My pussy was being really sensitive and responsive to my toying with it. I worked two entire fingers into it, and was running them around the interior of my pussy when he walked in.
He had his muscle shirt on, no underwear, and his cock was extremely hard. As he got closer I noticed that he had a cock ring on, and that was making him bulge out even more than he normally would. What can I say? It turned me on. I started to get up from where I was so that I could kiss him again, when he told me to lay back down. I did as I was told.
He got up on the bed, and crawled with his knees to get on top of me. I was breathing heavy, very excitedly. He kissed me deep and long, and I wrapped my arms around him, rubbing his strong shoulders as we briefly made out. He pulled my nightie up and started slowly kissing me all the way down my body. Once he passed my tits, he put his hands on them and began sweetly squeezing and rubbing them through my bra as he descended between my legs with his head.
I could feel him breathing heavier as he put his mouth on the front panel of my panties, and kissed my cock through the fabric, before going further down. He pulled my panties to the side and immediately stuck his tongue into my pussy. I couldn’t believe how fucking amazing it felt to have a man lapping at my sissy pussy. I naturally spread my legs even further, as he started spreading my ass cheeks open with his hands, and French kissing my quivering sissy cunt.
I was squirming in pleasure the entire time, which felt like forever, but in reality was only 3 or 4 minutes. He stopped abruptly, and quickly scurried his way back up my body, then started kissing me aggressively. We were both breathing heavy, I had my arms around him again, and was holding him as close to me as I could when he pulled up from me.
He scooted on his knees over to his nightstand, with his engorged cock at eye level with me. He took a sniff of poppers, and then offered me a sniff, which I also took. He told me to hold it as long as I could, and as soon as I exhaled, he told me to take 2 more and hold it as long as I could, which I did. My head was spinning, I felt every inch of my body tingling, and no sooner than I exhaled, he put his cock on my sparkling pink lips and plopped it into my mouth.
As the waves of synthetic euphoria rushed over my body, I began fucking his cock with my mouth. I was breathing through my nose, and had his entire throbbing rod all the way down my throat, and his balls were bumping into my chin.
“You look so sexy,” he said, gently thrusting his cock in and out of my sparkly lips. “You’re so good to me, you make me feel so good, baby.”
With each compliment, I got a little more intense with my mouth. I was kissing it, licking it, sucking it like it was the fountain of life itself. There’s nothing that turns a girl on more than being complimented about how beautiful she is as she is giving you sexual pleasure. His words made me feel like a sexy woman, and I liked that feeling. I liked it a lot.
The apparatus he had around his cock to make it so hard was almost like some sort of rubber band that was harnessed around his balls, which made his entire package almost look like what someone would draw if asked to depict a cock and balls. After slobbering all over his cock, I made my way down the shaft, where my lips and nose were practically on his hairless balls. As I put them in my mouth, he pulled them out and looked at me, before bending down to my face and kissing me.
“My balls are really sensitive, understand, baby?” he whispered to me, and I nodded in agreement with him. “Don’t suck them hard, you can lick and kiss them, but if you’re going to put them in your mouth, be gentle, okay?”
I let him know I understood by licking and kissing his balls tenderly, then putting one single ball in my mouth, and gently sucking on it while running my hand all around his ass and taint. The sounds of pleasure he was making let me know that I was doing a good job. He took a hit of poppers and then bent over me just enough to get his hands to my crotch. He rubbed my hard clitty through my panties for a few seconds, before pulling my panties over to one ass cheek and sticking 2 fingers inside of my sissy pussy.
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