Batwoman meets Catwoman Part One
- 2 years ago
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Old Man Porn Turns To Old Man Pleasure free porn video
When I was around about 19 my new favourite porn genre was 'old man and teen girl'. It all began one day when I was there jerking off and I began to imagine myself as the girl... Wearing the heels, dress and sucking a cock. I remember It made me super horny and I came really quickly. It was the first time I'd ever fantasied about anything sexual with another man. Over the following year, more often than not, when I was jerking off it was to older guy porn. Sometimes it would be straight porn, sometimes gay and I even liked older guys fucking ladyboys, but it was always older guys. The fatter and hairier the better.
One time I went out with a few friends at uni, we got back super wasted and someone suggested we go on chatroulette (this was when it first took off) so anyway we all got in a group and tried it, and low and behold we got a lot of wanking guys. This got me so horny that I left my flat mates room when straight to mine and searched 'gay chatroulette'. I spent literally a good 4 nights a week on that site looking for older men, and that's where I met Greg (not his real name).
Greg was in his mid-fifties and also British like me, then chatroulette would often cut out so he gave me his Skype the first time we met and messaged for a while, I told him exactly what I'm telling you know. How I realized I had an older guy fetish, and that I like the idea of maybe dressing as a 'sissy'. I didn't know how far I wanted to take it but it made me super horny. Greg explained that he was a married man, but he had a thing for younger guys, hence why he was speaking to me. He also liked sissies etc and said he been in the scene for a good 20 years, although I didn't tell him where I was located he told me where he lived and it was only two hours away by car, he wanted to meet me. Said I could make all my fantasies come true.
Him and I would Skype each other, a couple of times a week. I would show my self to him, tell him how much I wanted his cock in my mouth, in my arse. Tease him. Once I got to know him better he would send me things to my uni accommodation. He sent me lube, underwear, toys etc. With time he wouldn't Skype me alone, he'd be joined by a friend. I said fine as long they're older too... I loved playing with myself while they gave me compliments. I got to the point where I made the decision to meet them in person and take it to the next step...
We met in a hotel in the city where he lived, he told me he'd be waiting for me at the hotel reception and that two of his friends would be there as well. I was nervous, so nervous. But I knew if I backed out id regret it. I organized with Greg the night before what I wanted to do and my boundaries, he gave me his word they knew this and the night would be about me. I went in to the hotel room and the two guys where both in bathrobes laying on the bed watching the TV.
Greg said he'd just showered before I got there and that he'd get changed too. I went to shower, in the bathroom, there were a pair of suspenders, heels, a thong, a corset, a blonde wig, a mask that covered the upper half of my face and perfume. He told me to shower and let me know when I'd finished and he'd help me with the wig, corset etc. I remember I was so nervous when showering my dick went so tiny. I dried myself and called him, he did up my corset and did the wig and then I walked out.
Greg went and sat with the other two guys on the bed. They all had their cocks in their hands, and told me how sexy I was. I apologized that I couldn't walk in heels very well, they said that's what made it so sexy. I began to relax at this point and had a few drinks while we spoke.
I didn't really know what to do, but I said I love the way you all look at me, I felt so hot, they way they lusted at me. I told Greg that the night before I wasn't sure how far I could take it on the first night. I just sat there looking at them not sure what to say, horny but still nervous. Is started when one of guys asked me to pass him a towel from the bathroom as his precum was dripping all done his cock. I said to him. 'Why don't I come other there and use my sissy tongue to clean it up Daddy?' Just by saying that he groaned with pleasure and told me to go other there.
I slowly licked his cock, teasing him, moving down to his balls. He kept saying 'good bitch' 'daddy's little girl', Greg then said that he needed to be cleaned up too and so I went and did the same to him. But this time is started to suck as well. I loved hearing him moaning. The guy whose cock I licked came behind me and started slowly rubbing my asshole and balls, I stated moaning softly as I sucked of Greg and the other guy.
Greg said he was close to finishing, and the other guy began to moan so deeply I knew he was already on the way, I kind of lost my nerve and tossed him off to finish. His cum landing on his belly, I wanted to taste it, as it was my first time so I licked a bit of his belly and realized it didn't taste so bad, so I said to Greg I want you to finish in my mouth.
I took Greg in my mouth and started sucking him long and hard. While this was happening, the first guy had moved to fingering my asshole, and the guy who had finished was laying next to me on the bed, slowing jerking my cock. Greg finished all of sudden filling my mouth with so much cum it dripped down my mouth.
At this point I felt so adventurous, that I asked the guy who was fingering me to stick his cock in my arse and fuck me, that we didn't agree on the night before but I thought fuck it. I've taken a mouth full of cum I might as well go all the way. He put on a condom, and I slowly eased by self back on him. he fucked my slowly while rubbing my lower back, I loved the feeling, just as it started to hurt a bit he told me he was going to finish. He turned me on my back took of the condom and came all over my balls, cock and belly, the biggest load so far.
So there I was, lying on a bed in a Travelodge hotel. Covered in cum, sucked my first cock, swallowed my first load, lost my anal virginity and had dressed as a sissy for the first time. I got up went to the bathroom and still wet with cum i tossed my self off quickly, it took like ten seconds to blow.
I made a deal with Greg the night before that after we were done I just leave by myself. I didn't really want to hang around, so I showered got changed and headed out of there after saying goodbye.
And that was that, I got it on with Greg a couple of more times over Skype but i never met them again in person. I still think about it sometimes when I jerk off. Even today. I check out older man porn still, and even gaychatroulettes, but that was the first and last time I sucked a dick, In fact I'm now a married man.
But if you're an older guy, and you were in the room with me right now. I'd have you dick in my mouth in a heartbeat... ;)
Kaidence
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