The Misadventures of the World s Worst Sissy
- 2 years ago
- 30
- 0
First Adventure Into Sissy Land free porn video
Going back a few years is when my new beginning started, like many other married men out there - I still wake up with a hard-on, and have many sexual desires the problem my wife has zero desire. Our sex life started to drift about 7 years ago, we went from having sex 3-4 times a week to once or twice, they a few times a month, then eventually nothing. Sounds familiar?
I got tired of begging and being turned down, so I went to an old friend ‘porn’ and to jerking off just as I did before I got married. This was good, I was getting my fill of sex and fantasy even though it was with myself. The problem is that it was getting boring watching the same old in-n-out and blow jobs.
As I started to explore to keep my interest and desires going - I look for newer views like MMF, Cockold, etc. this got me thru for a while, but I kept on exploring. I then started to post my parts on xhamster – that was exciting taking photo’s and posting them for all to see. I was getting reply’s from some couples, but mostly men who were in the same situation as myself and how they were getting off looking at my cock, so I ventured into it also – which was a very exciting, especially sending photos back and forth and expressing our desires for cock. I started to have the realization that I wanted to suck a cock, I was jerking off looking at cocks and guys sucking and how they were enjoying it.
It wasn’t long after that, I got a friendship request from a Sissy named Debi, I accepted the request and didn’t pay too much attention – then I started getting more invites from Sissies - since I was a friend on her site. I started to pay more attention to their sites and found my dick perking up.
My wife was away for the day, and I decided to see how it felt putting on some of her undies – which were pretty ordinary, but I have them on and I got an instant hard-on. I danced around the full-length mirror poking my cock out from time to time, getting more excited. I then got out of her undies and put on a pair of her panty hose, wow my dick was raging seeing it hugged inside her hose. Memories of my youth rushed back to me, when I used to get dressing up in my Moms dresses and shoes – I found my next adventure.
It wasn’t even a week before I went out and bought some sexy undies of my own, but it was another week before I was alone long enough to try them on. I and get back in front of that mirror and had an instant hard-on, knowing that I may not get the opportunity being alone again for a while, I got my phone and started to take photos of sexy me. I decided to put them onto my site, the comments and chats started from guys telling me that I looked hot and they wanted to fuck my face and ass off, reading their emails got me off many nights.
As time passed, I had some long chats with Debbi, the gurl who started all this – she lived not too far from me, we would be online with each other and she would always tell me of her sexual adventures while I jerked off. I finally gave in and decided to meet her one afternoon. I was very nervous when I got to her apartment, she answered the door all done up, and looked very sexy. We talked and had a drink till we both felt comfortable, then she got up and said ‘let’s see what we got here’ undoing my pants she was happy to see I had on my new panties, she then began to rub my cock – as she did that she lifted up her skirt, my eyes were glued on the bulge in her undies. It wasn’t long before I was getting my first sissy blow job, BTW this was much better than I ever got from my wife… I was just about there – I said I’m going to cum, that was like a green light to her to go harder till I popped, she sucked me dry, when she finally took my cock out of her mouth, she said ‘OK you’re done, go home - I have things to do sweetheart, next time you do me’ Before I left she gave me a gift, ‘this is for you, practice if you want to be a gurl’ she then gave me a big wet kiss – I could taste my cum in her mouth. I got in the car and opened up the present, it was a very lifelike dildo!
When I got home, I couldn’t wait to play with my new toy, I always wanted one but was too shy to go and buy one. Finally after a few days I had a chance to play, I practice in the mirror sucking on it and seeing how far I could take it without gagging, then I lube up the dildo and my man hole, it wasn’t easy but after about 15 minutes I was making progress, but I was running out of time before the wife got back. Over the next few weeks, I was able to practice some more.
I was able to get away to see Debbi after a few weeks since are first encounter. I was hanging out to meet backup, I got to her place - she was wearing a flowing robe looking quite sexy. She led me in closed the door and then she wrapped her arms around as she started kissing me, I didn’t think I would ever kiss a man, even one dressed up as a girl! I could feel my cock rubbing against hers, and we were both getting very hard and excited. She took me by the hand as we went into the bedroom, off came her robe and I could see the outline of her cock thru her pink panties. In the back of my mind I remembered what she said before I left the last time ‘next time you do me’ that phrase kept repeating in my mind since we last met. I knew I was going to have her cock in my mouth at any moment, I was dizzy with anticipation – I slowly worked my way down from her neck, as I got down on my knees where I started mouthing her cock thru who panties.
I was so hard and full of desire, I grabbed her panties and slowly pulled them down exposing her cock. I enjoyed admiring this beautiful cock. I started to feel it up and down with my hand, then I moved forward and rubbed it lovingly over my face and began kissing it. Finally I let it enter into my wet mouth, taking it out - looking at it the wetness from my mouth, then putting it back in getting it deeper into my mouth - I went on slowly and lovingly sucking her sweet cock. She knew I was not just sucking her cock - I was making love to it, enjoying every the feeling of it in my mouth as I worked it. She then started to hold my head and pump me, forcing me to pick up the pace, it went from making love to being face fucked, and I reacted to the moment - I knew she was going to cum – then she let loose shooting her hot cum in my mouth, some I swallowed some came out the side of my mouth, I kept sucking as the whole feeling in my mouth changed by her cum. As Debbi started to get soft, her cum acting as a lube as my lips slipped and slide around her cum coated cock head – that was so good it made the ending was just as good as the beginning.
She praised my new cocksucking skills saying ‘you enjoyed that too much sweetie’ then she said ‘you’re done, now go home’ I didn’t get to blow my load, I was hard all the way home – my balls were aching.. I got into the house, the wife was asleep – so I went into the toilet and jerked off thinking of how I loved sucking cock.
Wait till I tell you the rest of this adventure – So, stay tuned…
I got tired of begging and being turned down, so I went to an old friend ‘porn’ and to jerking off just as I did before I got married. This was good, I was getting my fill of sex and fantasy even though it was with myself. The problem is that it was getting boring watching the same old in-n-out and blow jobs.
As I started to explore to keep my interest and desires going - I look for newer views like MMF, Cockold, etc. this got me thru for a while, but I kept on exploring. I then started to post my parts on xhamster – that was exciting taking photo’s and posting them for all to see. I was getting reply’s from some couples, but mostly men who were in the same situation as myself and how they were getting off looking at my cock, so I ventured into it also – which was a very exciting, especially sending photos back and forth and expressing our desires for cock. I started to have the realization that I wanted to suck a cock, I was jerking off looking at cocks and guys sucking and how they were enjoying it.
It wasn’t long after that, I got a friendship request from a Sissy named Debi, I accepted the request and didn’t pay too much attention – then I started getting more invites from Sissies - since I was a friend on her site. I started to pay more attention to their sites and found my dick perking up.
My wife was away for the day, and I decided to see how it felt putting on some of her undies – which were pretty ordinary, but I have them on and I got an instant hard-on. I danced around the full-length mirror poking my cock out from time to time, getting more excited. I then got out of her undies and put on a pair of her panty hose, wow my dick was raging seeing it hugged inside her hose. Memories of my youth rushed back to me, when I used to get dressing up in my Moms dresses and shoes – I found my next adventure.
It wasn’t even a week before I went out and bought some sexy undies of my own, but it was another week before I was alone long enough to try them on. I and get back in front of that mirror and had an instant hard-on, knowing that I may not get the opportunity being alone again for a while, I got my phone and started to take photos of sexy me. I decided to put them onto my site, the comments and chats started from guys telling me that I looked hot and they wanted to fuck my face and ass off, reading their emails got me off many nights.
As time passed, I had some long chats with Debbi, the gurl who started all this – she lived not too far from me, we would be online with each other and she would always tell me of her sexual adventures while I jerked off. I finally gave in and decided to meet her one afternoon. I was very nervous when I got to her apartment, she answered the door all done up, and looked very sexy. We talked and had a drink till we both felt comfortable, then she got up and said ‘let’s see what we got here’ undoing my pants she was happy to see I had on my new panties, she then began to rub my cock – as she did that she lifted up her skirt, my eyes were glued on the bulge in her undies. It wasn’t long before I was getting my first sissy blow job, BTW this was much better than I ever got from my wife… I was just about there – I said I’m going to cum, that was like a green light to her to go harder till I popped, she sucked me dry, when she finally took my cock out of her mouth, she said ‘OK you’re done, go home - I have things to do sweetheart, next time you do me’ Before I left she gave me a gift, ‘this is for you, practice if you want to be a gurl’ she then gave me a big wet kiss – I could taste my cum in her mouth. I got in the car and opened up the present, it was a very lifelike dildo!
When I got home, I couldn’t wait to play with my new toy, I always wanted one but was too shy to go and buy one. Finally after a few days I had a chance to play, I practice in the mirror sucking on it and seeing how far I could take it without gagging, then I lube up the dildo and my man hole, it wasn’t easy but after about 15 minutes I was making progress, but I was running out of time before the wife got back. Over the next few weeks, I was able to practice some more.
I was able to get away to see Debbi after a few weeks since are first encounter. I was hanging out to meet backup, I got to her place - she was wearing a flowing robe looking quite sexy. She led me in closed the door and then she wrapped her arms around as she started kissing me, I didn’t think I would ever kiss a man, even one dressed up as a girl! I could feel my cock rubbing against hers, and we were both getting very hard and excited. She took me by the hand as we went into the bedroom, off came her robe and I could see the outline of her cock thru her pink panties. In the back of my mind I remembered what she said before I left the last time ‘next time you do me’ that phrase kept repeating in my mind since we last met. I knew I was going to have her cock in my mouth at any moment, I was dizzy with anticipation – I slowly worked my way down from her neck, as I got down on my knees where I started mouthing her cock thru who panties.
I was so hard and full of desire, I grabbed her panties and slowly pulled them down exposing her cock. I enjoyed admiring this beautiful cock. I started to feel it up and down with my hand, then I moved forward and rubbed it lovingly over my face and began kissing it. Finally I let it enter into my wet mouth, taking it out - looking at it the wetness from my mouth, then putting it back in getting it deeper into my mouth - I went on slowly and lovingly sucking her sweet cock. She knew I was not just sucking her cock - I was making love to it, enjoying every the feeling of it in my mouth as I worked it. She then started to hold my head and pump me, forcing me to pick up the pace, it went from making love to being face fucked, and I reacted to the moment - I knew she was going to cum – then she let loose shooting her hot cum in my mouth, some I swallowed some came out the side of my mouth, I kept sucking as the whole feeling in my mouth changed by her cum. As Debbi started to get soft, her cum acting as a lube as my lips slipped and slide around her cum coated cock head – that was so good it made the ending was just as good as the beginning.
She praised my new cocksucking skills saying ‘you enjoyed that too much sweetie’ then she said ‘you’re done, now go home’ I didn’t get to blow my load, I was hard all the way home – my balls were aching.. I got into the house, the wife was asleep – so I went into the toilet and jerked off thinking of how I loved sucking cock.
Wait till I tell you the rest of this adventure – So, stay tuned…
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