Sissy Date Night with Danny

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Last minute plan change leads to a good sissy fucking!
1.9k words
4.66
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One Thursday night I was out country dancing in boy mode and it hit me like a shockwave, I wanted to get home, get all sissied up and have a man over to play with. Just out of nowhere I was one horny sissy!

There was a Man a few weeks earlier that I had a lot of fun with and he had given me his email address. I knew he had a girlfriend so it was a shot in the dark. Especially on a weeknight. So as I got in my car to leave the bar I took a shot and sent him an email asking if he wanted to come over.

I started to think about our last night together and I was getting plenty turned on thinking about his manly body.

Just then I remembered one thing he said at the front door as he was leaving. He said

" I can tell by the way your body moves that you are just dying to get fucked. Next time I am going to fuck you silly"

He was right! I needed a cock in me so bad that night. I'm sure I was arching my back, adjusting my panties and writhing around in that way that sissies do when they need a real man to fuck them.

The confusing part was that his personal ad where I met him specifically said he was not into bottoms. So I never brought it up, I didn't want to scare him off before I could at least suck his cock.

As all these thoughts were racing through my mind, I heard my phone ding that new email ding. Sure enough it was him and all it said was "yes, what time?" I was just pulling in my parking garage and asked him to give me 20 minutes to get ready. He said "Hurry up and get ready, I'm on my way"

I ran into my apartment and jumped into the shower. I used my girly smelling body wash that I always use for my dates with men. As soon as that fragrance hits my senses, my little sissy body knows what is about to happen. My mouth waters, my little boi pussy starts throbbing and my nips are so pert!

I picked out a little pink pair of panties, the lacy "boy short" type. I love the way they pull up in between, and separate my ass cheeks. I slipped on a white spaghetti strap tank top over a black bra. I was just wrapping up my make up when I heard Danny's knock on the door. I was so excited It felt like we were boyfriend and girlfriend and haven't seen each other for a week.

When I opened the door and said "Hi!l, I could feel my C cup silicone breast inserts bouncing with my sissy excitement at seeing my man, or at least my man for the evening.

Danny wrapped one arm around the small of my back, pulled me towards him for quick kiss at the door. I slipped a hand under his t shirt to feel his hairy body. I brushed my hand across his bulge and he seemed to be semi erect already.

We stood at the kitchen bar, I got Danny a beer and poured me a glass of white wine. I took a sip of wine set it down on counter and turned my attention back to Danny. He was telling me how sexy I looked, when I could not resist reaching out and rubbing his growing cock through his shorts. He pulled me towards him with his big hands on my sexy little ass cheeks. He was rubbing and groping my ass. My little tucked away clitty was rubbing against Danny's bulging shorts. I felt lighter than air as his strong hairy arms all but lifted me off the ground by ass. He seemed to pay particular attention to getting his big fingers to my smooth little sissy hole.

I noticed Danny's eye had caught the action playing the tv. Before he arrived I had chosen some sissy anal porn, hoping he would get the hint. I dropped to my knees in front of him and pulled his shorts down, his cock flopped out right in my face. Danny had a wonderful cock. At least 8", cut and thick. I had a fondness for the way it hung when it was half way erect. It was just so inviting when I was on my knees in front of him looking up. Danny is a tall man, probably 6'3" or maybe even 6'4". I took his cock into my mouth and just suckled on it like a sissy looking to get fed. As his cock hardened, I looked up at Danny. His eyes were alternating between the sissy porn on the tv and looking down across my girly arched back at my lacy panty covered ass. When Danny and I finally made eye contact. He suggested we go to the couch. Of course this Sissy does as her man wants.

Normally I would get on the floor, all nuzzled in between my man's legs. But, this time got on all fours on the couch to Danny's left. I wanted to make sure he had clear access to reach over and play with my little boi pussy if he was so inclined. Which I sure hoped he would! My head was in his lap with his big cock in my mouth. Of course right on cue, I felt Danny's hand rub across my lacy panties, his fingers finding my pink hole. With each rubbing motion his fingers would linger on my hole a little longer. He was just gently rubbing and pushing on my throbbing pink boi puss. I could feel his cock stiffen. The head of that purple monster would flare out and get even harder in unison with the touching of my pussy. I could tell my ass was really turning him on.

I had left a tube of lubricant on the arm of the couch to Danny's right. I didn't even notice him picking it up. I just felt his fingers were now wet and slick as he slid his hand under my panties. Danny resumed massaging my hole with his now slick, lubed finger while I slowly and methodically sucked His big cock. He took his time to really loosen me up, my pussy was starting to feel like gel to me. Like it was flowering and could be easily penetrated. When Danny slid that first finger inside of me, my back arched and my body writhed with pleasure. I was slowly pushing back with each involuntary arch of my back He easily added a second finger, then third. I was moaning and and moving like a sissy bitch in heat. I could not concentrate on sucking him as I moaned and moved my ass and hips in the most girly circular motion. This all went on for almost half an hour. I was in a trance, under a spell that I was suddenly awakened from when I heard Danny's voice say "it's time, go get on your bed.....I'm gonna fuck you"

As I crawled onto the bed I felt Danny's hand on my hip. I was on my knees at edge of the bed. Danny said " stay right there and let me get those panties off of you", I put my legs close together as Danny's hands took my little lacy pink panties down. I lifted first one knee and then the other and Danny knew just how to make a sissy feel so feminine in the way he glided those lacy panties off of my smoothly shaved legs.

I was adjusting the spread between knees when Danny took control. He took his hand to the inside of my thigh and moved my leg out to just where he wanted it. First one leg and then the other. My body was going crazy. I was writhing around, trebling, so ready for a good fucking. He put his hands on my hips and pulled my body back towards his.

When Danny had me positioned with my ass in the air on the edge of the bed, I felt the lube hit the small of my back. Danny's hand working the lube into my boi pussy with his thumb. My upper body dropped, my back arched. My shoulders were flat against the mattress. I could feel my big silicone breasts squishing and giggling between me and the bed. I was in full submission and ready to be a sissy fuck toy for Danny's use.

I felt the head of his big cock sliding up and down my ass crack, stopping at my little pink hole, putting a little more pressure with each pass. I could finally feel that he was was keeping his big hard cock head right there on my pussy. He was building the pressure against my hole. Suddenly I felt his hands on my hips, pulling me towards him. I relaxed, pushed back towards him and he was sliding into me. Slowly at first he pushed in, it hurt a little at first. But as I got used to it and we built a rhythm together it was amazing. As a sissy, the only time I really feel one hundred percent like a woman is when a man is fucking me.

As Danny's pace increased I could feel his balls slapping against my little limp clitty. His manly manly body hair rubbing against my smoothly shaved taint just affirmed that he was the man and I was the sissy. My god it took me to another dimension. Dannys body was clapping against mine full force. He fucked me like this for almost half an hour. He added lube one last time and I could tell he was about to blast his load inside of me.

Suddenly he slammed deliciously into me, pulled me hard back towards him by my hip and shoulder. He held his entire eight inches deep inside of me. Danny grunted and ground his cock, I could feel his pubic hair grinding against my smooth ass cheeks when he finally exploded. He pulled me back and thrusted forward, grunting with each pulse of his thick manly cum. My little clitty was dribbling as he pulled his big manly member out of me. His cock still so hard I heard it slap his belly as it left my Pusey. I fell forward flat on the bed in exhaustion Danny landed on top of me and just laid there for what seemed like an hour but was probably only five or ten minutes.

I was afraid he was gonna fall asleep on top of me when finally he asked if he could take a shower. When Danny hopped up to go the shower I just laid there, more relaxed than I had felt in months. This Sissy really needed a good fucking to get my mind right!

Danny and I got together every chance we could over the next five or six years. Sometimes going months without talking we would always seem to get it back together and have sex regularly. We finally lost contact and I moved out of state. Danny is definitely a man I still think about regularly, maybe even while I'm rubbing my little clitty!

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myjennysidemyjennyside18 days agoAuthor

Thanks to all of you for your feedback, it’s really fun reliving some of the revelries of my youth! I’m going to continue one of them, I will start tonight!

SuckergurlSuckergurl20 days ago

I absolutely love your stories 5*for all, there is plenty of room for follow ups on your first and second, I think you have probably done with number three, keep up the excellent work

ChloecrossedChloecrossed20 days ago

Danny sounds perfect; tall, masculine, hairy chest. I imagined that he had rough manly hands, which would feel sensational against my smooth delicate femme body, mmmmm. I agree that being fucked by a guy makes you feel totally womanly. I also love the act of getting ready for a date like this, that also heightens my femininity and erotic anticipation and enjoyment. ❤️

MichaelfantasiesMichaelfantasies23 days ago

You wrote so well about how you felt; how you prepared and dressed for Danny along with how his big cock teased your boy pussy before sliding inside you. You wrote, "As a sissy, the only time I really feel one hundred percent like a woman is when a man is fucking me." I 100% agree with that!

I really, REALLY miss that intimacy with a man.

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