Free Erotic Stories

Sexual punishment

The last year and a half has been very boring, due to the lack of in person to person sexual encounters, thanks to the pandemic. But now that I have taken steps to ensure that my partner's and I are healthy as possible, I have ventured back out to sooth my sexual thirst. I know there's no guarantee, just like with any other disease or virus. So after a few failed attempts with friends from the past, I started talking to a few new prospects and with all the precautions I could take with numerous chats and emails, I decided to give John a chance. ( name changed to protect the wicked ) We talked about our past experiences and future experiences we wished to fulfill. I dabbled a little with cross dressing way back when I was in my teens, you know, try on a pair of my sisters panties, a pair of pantyhose, and a nice one piece swimsuit once in awhile, I liked the feel of the tight garments against my hard cock as I rubbed it. So when John asked me if I would like him to dress up for me, my urges from the past took over in my loins and i told him "yes by all means " as we chatted about what he was going to wear when he meets me at the door, I never thought he would pass as a woman as much as he did, but what a surprise. We also talked about some roll play ideas, so the proceeding story is what happened that night when I arrived at his place. As I pull into a darkened driveway with the unknown about to happen, I can't help but be excited. John (strike that) Jennifer (is the name we came up with, for our adventure) had instructed me to just come in the side door, that's were she would be when I arrived. As I swung the door open and seen him for the first time I was in awe, he was dressed in a black stretchy one piece dress, black nylons, and a long black wig, he came over to greet me at the door and locked it behind me saying "we don't want to be disturbed " he then said "glad to see you home daddy " and leand in for a kiss, we stood there kissing for a few minutes and I went down with both hands to his ass and started squeezing both cheeks, as I did I hiked up the rear of his dress to feel the silky panties he had on. As my dick got harder, he reached down and started rubbing his hand on my crotch, I pulled away from kissing him and said "I was told you were a very bad girl today " and he replied "yes daddy, are you going to punish me " I said "yes, bend over the table " as he bent over and exposed his ass to me, I pulled his dress up over his hips, the nylons were thigh high and the silky panties he wore were black with a floral pattern, I rubbed his nylon covered legs to feel the smoothness and told him "I'm going to have to spank you, you dirty little girl " he replied with "what else are you going to do with me daddy? " I said you will see, as i gave his ass a few swats with my cupped hand and rubbed his panties after every single swat, I slid my hand over his man clit, it felt nice under those silky panties. I then changed my focus on punishing him further, so I grabbed the upper portion of his panties and yanked them down over his butt to expose his man pussy to me. I said to him "now for the second part of your punishment " I then pulled out a graduated bead wand, lubed it up and fingered his pussy with some of the lube,I then proceeded to insert the wand in until it was fully packed as far as it would go, I pulled his panties back up and told him to stand up. He turnd to me and asked how long he was going to have that in, I told him as long as I wanted to leave it there.we stood there and kissed as we rubbed each other's cocks. I said let's take this somewhere else and get comfortable, as he led me to the bedroom, I could see him walking like he had something in his ass, and of course he did. When we got to the other room we started kissing again, then I proceeded to remove his dress, as he stood there in just his panties and stockings l knelt down to my knees and pulled his panties all the way down exposing his now erect cock, I grabbed his butt with both hands and sucked his cock into my mouth, he was already oozing pre cum from the tip and I savored every drop. As he began to moan, I stopped and told him "don't you dare cum yet" he said "but daddy, your mouth feels so good on my clit" I repeated "don't cum". So I stood up, kissed him and instructed him to undo my belt, unhook my pants, and pull them down for me. As he did that I removed my shirt, and asked him if he wanted to see my cock? He said "oh yes please daddy, may I get it out" I told him to pull my underwear down, as he did my cock popped out and almost hit him in the face, it was so erect, that it almost hurt. I said to him "suck my dick" so he sat on the edge of the bed, and when he did the wand in his man pussy pushed up to remind him of its presence. He let out a bit of a whimper, and I said to him. "How does that play toy in you feel now you dirty little girl " he said "it hurts daddy, but I know I was bad" so I said "that's good, next time maybe you won't be such a dirty little girl, so daddy's going to fuck you tonight, and show you how bad you are" He continued to suck my cock, as I grabbed the side of his head with both hands and began to fuck his mouth with a smooth and even in and out pace. I admit I was just about to cum deep into his mouth after just a minute of this, so I quickly pulled my dick out and asked him if he could taste my pre cum. He said he could and it was definitely delightful. I instructed him to stand up so we could completely remove his panties. I then took my turn again to savor his oozing cock in my mouth as I got down to my knees, and had him open his stance a bit, so I could reach up and start playing with the beaded wand in his ass (or his man pussy) at the same time, as I pressed on the wand, he ended up surging forward and gagged me with his dick, so I pulled his cock out of my mouth and started to slowly stroke him as I played with the toy. I asked him if he wanted to cum, and he said "oh yes daddy, please may I cum?" I told him yes but to wait until I laid on the bed and cum on my cock. With his dick in his hand, he wasted no time after I got into position to straddle me at the hips and rubbed our cocks together until he cam, and man did he cum. It must have been so penned up, he blew his initial load up my stomach all the way to my nipples, and the remainder all over my throbbing dick. I said to him "now you can clean that up, you dirty little girl " he started by leaning over and we kissed for a brief moment, then he went to work licking his own cum off my body, starting with my nipples and working his way down to my dick. Once he was done cleaning up the cum he began to suck me into his mouth, but I told him to stop and lie beside me on his stomach, as he did I positioned myself over his legs and pulled his ass up and off the bed so his knees were under him, I then spread his knees and legs apart and repositioned myself in between them. I said "I'm going to fuck you now, you dirty little girl " and started to pull out the wand of beads from his man pussy, I have to say a little poo came out with the wand, but I was so erect and ready to fuck him it didn't matter. I grabbed the only condom from the night stand and hastily tried to put it on my swollen cock, but as I did, I ripped it to oblivion and my dick poked right through the end. So I pulled it off and thought, fuck it, and slid my erection right up to his poo and lubed covered hole and began pushing slowly until my dick was penetrating his slippery asshole. As I went further into him, I heard a sloppy slurping sound as I began to rhythmically pound his waiting ass, it felt so good that I knew it wouldn't be long before I would be cumming. As I pounded him from behind, I know that my balls were slapping his balls with every push, but I could only imagine what that looked like, and it really took me over the top. I asked him if he was ready for my cum in his man pussy, and he said "oh yes daddy, please cum in me, cum in me now" As I pushed for the last time and held his hips tight against me, I blew my load as deep inside him as I could. It felt so good I almost passed out from pure delight. My body trembled with uncontrollable pulses of delight as I released all the pent up cum within me, to within him. We both went flat on the bed and let out an exasperated breath of great joy as we just lay there and relish all that had happened in the last few minutes. We have meet up with each other on a few occasions since and just had great sex, as 2 men can, and actually invited another guy to join us once, that was as memorable as any other time in its self. But that's a whole other story

---