A slutty sissy spends an enchanting evening with a hot hunk

The year was 2024. My girlfriend was gone to Virginia to visit her family for a week, and it was just me and the dog staying in the house. We had a big, honking Gateway computer, and our dial-up modem was in full effect. I went by the liquor store on my way home from work, and after walking the dog, I promptly made a drink and got into a bubble bath as soon as I walked inside. I put on an Elvis CD as I stripped down and eased into the overflowing flowery bubbles to relax and leisurely clean myself up.

I had only ever been with one guy at this point in my life. He and I got together one night, and I was forced to reveal that I wear panties to him. I wrote about it in a previous story. We ended up getting together several times after that, and he would buy me panties, bras, nighties, etc, and we would fuck.

To be clear, he would fuck me, I would be the girl for him. It happened for years and while the sex was great, it also lacked in the intimacy department, meaning he would treat me like a fucktoy then act like nothing ever happened after he came.

Earlier in the day, I went home for lunch and self administered a mineral oil enema just in case anything wild went down later that night. I learned this trick from listening to 2 girls having lunch in a casino diner one day, and discussing trying anal for the first time. One girl told the other that her boyfriend told her to do it several hours before he picked her up, and that she had done so, and in return it, “didn’t feel that bad, and actually felt kind of good.”

Before getting in the tub, I followed with a warm water enema to make sure I had the all clear, and I did. I smoked a little bit of herb while in the tub to ease the stress of the day and welcome the weekend with open arms. After washing my hair and exfoliating my body with my girlfriend’s big, fluffy loofah, I grabbed her big pink razor and her pink can of shave cream, and proceeded to shave my underarms and face.

I can remember, “(You’re The) Devil In Disguise” playing, as I stood up and shaved my legs and entire crotch area smooth and clean. As I was finishing, I remember catching a glimpse of myself in the mirror and smiling. In moments like this, if I had to choose between being with girls or my lifelong desire to be a girl, I don’t know what my answer would be.

After covering my entire body in cocoa butter lotion, I proceeded to the bedroom to get dressed and sit down at the makeup table to make myself as pretty as I possibly could. I put on a pink floral satin bra and panty set, and a pink satin babydoll slip. I walked gingerly to the kitchen and fixed another drink, careful not to be seen through the windows by any of our neighbors, then went back to the makeup station.

I wasn’t the best at putting on makeup, but loved the process of applying foundation to smooth out my face as best as possible, then painting my eyes, cheeks, and lips. I have an affinity for pink sparkly lipstick. It really accents my lips well, and makes me feel sexy. After working on my face for about 20 minutes, I stood up and checked myself out in the full length mirror. “Not bad,” I said to myself, before blowing myself a kiss and going into the computer room to surf the web.

Dial up internet really sucked, but no one knew any better at the time, so it was fun and exciting to get online and interact with others. The whole experience was new to me, and to be honest, just sitting on the barstool we had in front of the computer, all dolled up in my slinky nightie and bra and panties was like heaven to me. I smoked cigs at the time, and opened up the windows to smoke inside while I sipped cosmos and looked around. *Side note – When you’re extremely turned on by being and feeling feminine like I am, simply seeing your lipstick prints on the rim of a glass is exciting.

The extent of adult content online at that point (at least to the best of my knowledge) was picture galleries. I would see the occasional video, but it would run really choppy, or take forever to load, etc. I searched online for pics or vids of trans or gay content, when I saw a link for “gay.com” I don’t know why this site ever went away, but it was amazing! Everything was easy to navigate, and you could enter your zip code to be connected immediately in a chat room with everyone in the area. Sure, it wasn’t high-tech, but it was way better than anything out there if you wanted to be interactive with others and feel shit out. If you chose to get one on one with someone, you could, but beyond that, the chat room was wide open and buzzing with tons of people.

After making small talk with a lot of people for about an hour and a half, a guy named Alan and I started hitting it off. He was about 8 years older than me, taller and stockier than me, and knew how to carry on a conversation. When I told him I was into crossdressing, he said that was hot, and when I asked him how he would describe what he wants in a lover, his response almost made me melt in my chair.

“I want someone who is sweet, cute, giving and caring, and who enjoys me taking the lead in the bedroom. I’m dominant, but not in an aggressive way. I just enjoy being the leader, and making my partner feel exhilarated, special, and voluntarily submissive to me because they enjoy the feeling of safety that I provide for them. Also, I love making out, cuddling before and after sex.”

My heart was pounding out of my chest. I could feel it pulsing in my throat and in all extremities. He hit a homerun with is response. When he asked me what I was looking for, I simply replied, “I’m looking to be exactly what you want in a lover, and I can’t wait to show you how good I am at following your lead.”

He sent a smiley face back to me and said, “Can you come over here tonight?”

I felt a rush run over me when he extended an invitation for me to come be with him. I slammed my drink as I rubbed on my crotch and started spreading my ass cheeks through my panties in order to wedge a finger in there. I knew I had to do this, so I told him I would be there in 30 minutes, and that I just wanted to freshen up first.

He replied, “Hey, I think it’s hot that you dress up, but for your own safety and to keep my own sexuality a secret to all of my neighbors, can you bring your girl clothes in a bag?”

This seemed reasonable, so I agreed. I touched up my makeup, took off my babydoll and packed it in a bag, then put on a baggy shirt, a pair of khakis, and a baggy jacket. I fixed another drink for the road, grabbed disc 2 of my Elvis collection, and headed out to see my man.

His apartment building was old, very cool, like it was built in the early 1900’s. My heart started beating faster as I walked up his stairs. I hesitated for a minute, telling myself I could turn around right now and no one would ever know I was here. That’s when I saw him looking through the window at me, smiling and waving. I was there, he saw me, this was happening, and I was excited.

I walked to his door, and he opened it right away, and asked if he could take my bag. He then leaned in and gave me a kiss on the cheek and a nice, welcoming hug. I hugged him back tightly, before he gave me a peck on the top of my head and told me I was welcome to go change in the bathroom if I wanted to. I told him that sounded great, thanked him, and proceeded to go into the powder room to change.

“Would you like a drink?” he asked from across the apartment. “Do you have a preference?”

“A Cosmo would be nice, thank you,” I said, as I pulled out my babydoll nightie and touched up my lipstick. I looked at myself in the mirror, draped in satin, and in full makeup, and gave myself a kiss and a wink before walking out to meet Alan.

He had Marvin Gaye playing on his stereo, and when I walked out, he was standing right there in front of the door in his boxers and sleeveless undershirt, holding my drink.

“Thank you, sweetie,” I said. He came closer to me, handed me the drink, and gave me another strong hug. He kissed my cheek again, and ushered me to the living room, holding my hand.

“Have a seat on the couch, baby,” he said to me, as he was closing the blinds and lighting candles. He asked if I minded that he smoked, and I told him I was glad that he smoked, because I would love one as well. He grabbed an ashtray, gave me one of his Camel Lights, and lit it for me, before sitting down next to me.

Apart from one guy back home that I used to mess around with, I was very inexperienced in being with men. When I hooked up with my buddy back home, it was always done very late at night, typically in silence, and never felt like anything beyond straight up sex. This felt like a legitimate date, not just a meet up to fuck, and that turned me on a lot. Being treated like a woman outside of the bedroom was something I had never experienced, and I loved it.

As we sat there having a drink and smoke, in a sparsely candlelit room, while the sweet soothing sounds of Marvin were playing softly in the background had both a calming and aphrodisiac effect on me. He fondled my neck and shoulder gently with his hand, and started asking me questions. He asked me things like, if I was out of the closet, when I started experimenting with women’s clothes and if I had been with a lot of people. I told him that not only was I not out of the closet, but I also had a girlfriend, and that I had been drawn to women’s clothes for roughly my whole life, then told him that I had only ever been with one other guy in my life.

“That’s fascinating!” he said, as he moved in closer to me and started massaging my neck a little stronger than he had previously been doing. It felt so comforting and soothing to me. He continued, “So you’re telling me that this is only the second experience with a man you’ve ever had?”

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.

This made everything we were doing intensify greatly for me. I took my mouth away from his balls, put his pulsating cock back into my throat, and began moaning sweetly while I slobbered all over his dick. He began saying things to me again.

“Your sweet little pussy is so tight. It feels amazing, baby.”

As I began sucking harder, I stopped to say, “You like my tight pussy, daddy? I kept it tight for you, daddy.”

As he began fingering me a little harder, I was gyrating my hips, trying to find the motion of his fingers and syncopate with his rhythm.

“I appreciate that tight pussy, baby, and I can tell you’re not lying when you say that you haven’t been with hardly anyone, because your pussy feels like a virgin’s pussy. It’s amazing.”

I was floating on clouds of erotic pleasure, being told how amazing and beautiful I was, as I was sucking his gorgeous cock. I began to taste a little bit of pre-cum in my mouth, and no sooner than it hit my tongue, he abruptly pulled back from me.

“I don’t want to cum, I want to fuck you,” he said.

“I don’t want you to cum, I want you to fuck me, daddy,” I said in response, as he smiled at me and fondled my cheek with his hand.

“How do you like to be fucked?” he asked, as he was grabbing the lube and a condom, and tossed the popper bottle to me.

The only other guy that fucked me liked to do it doggy style or while I was laying on my side. I liked both of those, but like I said earlier, it never felt very intimate. Don’t get me wrong, I love being objectified, and never understood how gorgeous girls would act so bummed out about being seen as sexual objects, but I wanted to experience something on a different level.

“I want to do it missionary style,” I said, “I want to make out with you, I want you to see the expressions on my face, and be able to feel the weight of your body on me while I hold on to your back and you fuck my brains out.”

“That sounds amazing, baby,” he replied. “Let’s do this. What’s your girl name?”

I replied, “Call me Katie, daddy.”

“Katie, I need you to take one of those pillows behind you and put it under the small of your back.”

I did as I was told. He quickly shimmied his way down to the end of the bed as I fixed the pillow under my back. He kissed my clitty again through my panties, then pulled them partially down and took it into his mouth. It felt amazing, and just when I thought it couldn’t feel any better, he wedged his 2 fingers back inside of me and started circling around my sugar walls.

I asked him to bring his cock to my mouth, but he resisted, and told me that I would get his cock soon enough, but right now is all about making me feel good. He continued sucking on my clitty and fingering my pussy. I felt like I was going to explode, and cum down his throat. He must have felt it, too, or he must have tasted a dribble of my girly cum, because he immediately pulled back and away from me.

“How long has it been since you were fucked by a man, Katie?” said Alan, panting heavily as he ripped the condom open with his teeth.

“It’s been at least 3 years,” I replied, “I’m hoping I am able to take all of you.”

He smiled, came forward to kiss me, and after doing so, said, “Oh, we’ll make sure of that, Katie. It’s going to take some easing into it, but we’ll get there. Grab those poppers, baby.”

I did so while watching him trying to fit the rubber on his engorged cock. Once he got it on, he began giving more instructions.

“Make sure the pillow is in the right place, I need it to help angle your pussy up to me, ok?”

I nodded in agreement, and wedged the pillow into the right place. He took some lube and applied it to his dick, then took a little more to put in my pussy. As he was pulling my panties off, I asked him if he wouldn’t mind just pulling them to the side, but he would have none of it.

He said, “Maybe we could do that if we were fucking doggy or you were on your stomach, but I think they would just get in the way if we’re fucking missionary style, and I don’t want to ruin your pretty panties, or have them invading my territory as we’re making love. Does that make sense?”

I told him that it made total sense, and with that, he pulled them down. He left them hanging on one of my legs, and he jumped back up and into position. He began plopping his cock on top of my clitty, then sliding it down between my legs to my pussy. When he got there, he would tease my pussy lips by barely nudging the smallest portion of his cock head in it briefly, then pulling back. It felt fucking amazing to be laying on my back, and experiencing this for the first time ever. He repeated this a few times, each time feeling better than the last.

He came back up to my face, kissing all the way up my body until he reached my lips. I was breathing heavy, in a state of ecstasy the entire time. After kissing me for about a minute or so, he gave me my next instructions.

“Whenever you’re ready for me, let me know by taking 2 hits off of that poppers bottle. Hold the last one as long as you can, ok?”

I replied, “Yes, daddy,” and took the bottle into my hand.

Again, he plopped his big, fat rod onto my clitty and ran the head of it down between my legs, and was slowly circling my pussy. I couldn’t take it anymore, so I unscrewed the bottle and took the first sniff. I held it for about 10 seconds or so, then took my next hit. I held it for closer to 15 seconds, before finally exhaling.

At the moment of exhalation, he took the head of his cock that had previously been circling around my pussy, and stuck it inside of me. My head was swimming from the poppers, and every bit of me was relaxed when I felt him enter me. I gasped in equal parts pleasure and pain. My eyes had been closed, but they opened as soon as I felt him, and as soon as I began to squeal, I looked up at him, and he put his finger to his lips, telling me to remain quiet. I did as I was told, and bit my lip.

He didn’t move his cock from where it was. He left the head inside of me, and went no further for about a minute. He took the poppers from my quivering, clenched hand, and took a hit. He handed it back to me, and told me to take two more sniffs. I did what I was told, and took a third for good measure. I held the last one for about 15 seconds, and as I exhaled, I looked up at Alan and smiled.

With that, he took each of my spread legs and wrapped his arms around them to lift them up slightly. He then started coming towards me to kiss me, and as he did, he slowly but deliberately put as much of his cock inside of me as he could as soon as we locked lips. I was moaning, but it was muted by his furious French kiss, as I felt all of his body weight overpowering me, and my pussy being completely and wantonly stuffed to capacity.

He didn’t move at all. He kept his cock firmly in me, but didn’t go in and out for at least 2 or 3 minutes, while we kissed passionately. The waves of pleasure inside my body were intensely smashing into the seaboard of my soul. I threw my arms around his shoulders, and began running my arms up and down his back. I thought to myself, “So this is what it feels like to be woman, eh,” before everything changed and got even better.

“Take a few more sniffs of those poppers, Katie,” he whispered into my ear.

They were clinched in my hand, but I couldn’t really do it in this position, on my back, with a man inside of me. Alan sensed this, and grabbed them out of my hand, unscrewed the top, and administered 3 sniffs to me, telling me to hold the last one as long as I could. I did what I was told. He took one big sniff as well.

We both exhaled at the same time, and as soon as we did, he began pulling his engorged cock out of me. As soon as the tip of his head exited, he quickly thrust it right back into my pussy, and kept it all the way inside. He would back up about an inch, then bluntly force it all the way back in. My heart was pounding out of my chest in pleasure.

My clit had gone totally soft, and began leaking girly cum with each pump he gave me. I wasn’t fully cumming, but it was very orgasmic, nonetheless. The cum was clear, it almost looked like water. Alan noticed it, and wiped it up with his fingers, putting one finger in his mouth, and delivering the other to me. It was yummy, and tasting it made me produce more. I was being made into a girl by a handsome, hung, gentleman.

He began picking up the pace, pushing my legs further backwards, to where my knees were at my eye level, and plunging his whole cock in and out of me methodically as he kept kissing me. My hands were busy going back and forth between his back and his chest, rubbing him down lovingly as he kept digging into my soul. My pussy had fully accepted him, and I could feel his balls slapping into my ass with every stab his cock was administering.

He began slowing down, much to my dismay. He was still pouncing his cock into my pussy that was exploding with sensations I had never felt before, when he pulled his body off of mine. I was on my back, and he had my legs pinned as far as he could push them, and he was towering over me, still inside of me, but not moving. He had sweat rolling down his brow, and his sweaty chest was glistening in the candlelight. We were both breathing heavy, like a couple of dogs who had just chased the mailman for several blocks before giving up.

“Goddamn, you look beautiful,” he said to me, “absolutely fucking beautiful.”

I cooed in appreciation, and tried to grab his hips to pull him back on top of me, but he resisted my efforts. He grabbed the bottle of poppers, and took 2 real quick hits, one in each nostril. He handed the bottle to me, and gave me instructions.

“You need to take 2 sniffs in each nostril, as big as you can handle, then hold the last one for as long as you possibly can.”

I nodded in agreement, and he continued,

“Once you exhale, I need you to grab your ankles, and pull your legs back as far as you possibly can and hold them. Understand?”

I replied, “Yes, baby, you’re the boss, just don’t stop fucking me, daddy.”

I unscrewed the bottle, and inhaled as hard as I could. I rotated back and forth between the two nostrils, and on the last sniff, I held it for 15-20 seconds. As I exhaled, he let go of my legs, and I grabbed hold of them, pulling them back as far as I could. The effects of the poppers were kicking in strongly, and my entire body felt like it was on fire in the greatest way possible.

With that, he remained kneeling over me, and pulled his cock out briefly, before smashing back inside of me as hard as he could. I thought my eyes were going to pop out of my head, and it felt like his cock was in my stomach. He began thrusting fully inside of me at a feverish pace, when I felt my entire libido begin tingling intensely. He put his hands on my waist, lifting me up off of the pillow, and started thrashing into my pussy harder than anything I had ever felt in my life.

Before I could catch my breath, I started feeling warm liquid hitting my face in fevered spurts. Confused at first, I looked down and saw that it was my sissy cock spurting all over my chest and face, and into my mouth, nose and eyes. I licked up whatever I could, and started squealing like a bitch in heat as he methodically pounded my engorged hole harder and harder. My words were coming out one at a time, in between gasps for air.

“Oh. My. God. Daddy! Fuck. Me! Fuck. Me! Fuck. Me! I. Want. To. Eat. Your. Cum. Daddy. Oh. My. God. Daddy. I. Want. Your. CUM!”

He pumped into me about 10 more times, as hard as he could, then whipped his cock out, and frantically pulled the rubber off as he moved up my body, pinning my arms down with his knees, and ramming it into my mouth. The cum was gushing out with such force that it filled my mouth and throat in a matter of seconds, and I began choking on it, gasping for air. He was lost in his own orgasm, and kept on pumping his cock down my throat as hard as he could, groaning, thrusting, exploding.

I began to catch my breath, and was cleaning up everything that I could, despite my arms still being pinned down by his knees. He let one knee off of my right arm, and I began wiping all of his man juice that I could reach with my hand and scooping it into my mouth. He was finished cumming, but left his cock in my mouth at my insistence. I suckled on his cock like it was a lollipop, and kept it as far down my throat as I could for as long as I could, until he pulled it out of my lips and got off of me.

I was laying there, drenched in sweat and cum, still panting loudly, and my whole body was squirming in satisfaction, when I saw him bending over me and putting my cum drenched squishy soft cock and balls into his mouth, and sucking them sweetly as he cleaned them of all bodily fluids.

My legs were still instinctually halfway bent backwards from getting fucked so hard, and as he got up, he took my panties that were dangling from my right ankle, grabbed my quivering left leg, and began to pull them back up, placing them back in place over my tingling, emasculated clit and pussy.

With that, he laid down next to me, and put his arm around me. I immediately cuddled up to him and ran my fingers through his chest hair as I kissed his nipples and soaked in his amazing aroma. He lit a cigarette, took a few puffs, then put it up to my lips. I did the same, and we shared it in silence as we both laid there. I fell asleep in his arms, drenched and exhausted.

I woke up in his arms at 5am, but he was still racked out hard. I used the bathroom, put on my depressing man pants and jacket, freshened my lipstick, and wrote him a note:

“Thank you for the greatest fucking night of my life, daddy! We MUST do this again, and do it again soon! XOXO”

I left a big smooch at the end of the letter with my lipstick, and quietly left to go home and let my pup out. As I walked out of his place, I reflected on what had just taken place, and how amazing it felt to be treated like the woman I knew I was by a sweet and capable man. I was truly born in the wrong body, and as much as it pains me to live life knowing that my biological formula wasn’t correct upon my entry to this world, I derive hope from experiences like this. If this was all that I had to cling to in order to feel normal once in a while, I would gladly take it.

The sun wasn’t up, it was cold, and my bra that was still drenched in sweat and cum was making my chest cold. In turn, the feeling it gave me on my tits immediately got me excited again, and I ran home, grabbed my vibrator, and dicked myself down to sleep. Such is the mind of a slutty sissy.