How I Became a Sissy: A True StoryI was about 48 years old, happily married man when my wife became seriously unwell and was admitted to the hospital. She had a major operation and faced an extended stay while recovering. This led to me relying more and more on internet porn to get my rocks off. On this particular day, I was browsing my go-to porn sites and came across a movie with a stunning-looking blonde giving a guy a blowjob and letting him throat-fuck her. It did the trick, and soon I was pumping my cum into a handful of tissues. Feeling satisfied and no longer horny, I was about to turn off my computer. Just as I did, the camera zoomed out to a wider shot and revealed that the stunning blonde had a cock and was a transvestite. I was shocked that I had beaten my meat while watching tranny porn. However, it obviously planted a seed in my mind.The next day, I found myself browsing porn sites again, but this time I searched for tranny and crossdressing porn. I found myself getting aroused by what I saw, and again I started to masturbate while watching what were clearly man-on-man sex movies. I started to imagine it was me dressed up in stockings and lingerie, sucking a guy's cock and swallowing his cum. I began to ejaculate and produced more cum than I had in years. My orgasm was intense, and I couldn’t wait to do it again. That night while I was in bed, my mind went back to being dressed in sexy lingerie and pleasuring a man. I got up from the bed, my throbbing cock sticking out in front of me and bouncing up and down as I moved across the bedroom to the chest of drawers where my wife’s underwear was kept. I opened the drawer and searched through the panties, suspender belts, stockings, and tights that my wife had. I found some panties that I liked and slipped them on, struggling to push my erection down inside them. Then I took a pair of her tights that she had worn, washed, and balled up in the drawer. I carefully slipped them over my feet and pulled them up my legs. I loved the feel of the fine, sheer nylon on my skin. It also made my cock throb even more inside the panties I had on. I looked in the mirror and thought to myself how good they made my legs look. I lay back on the bed and began to fantasise that I was dressed up and a man—my neighbour—came into the bedroom. In the fantasy, he stripped off his clothes to reveal a gorgeous, meaty, hard cock, which he ordered me to suck. I gladly did as he asked. I was sucking and licking him when he said, "I am coming, swallow it you bitch." I then began to orgasm at the exact same time. I fell asleep on the bed, still dressed in my wife’s panties and tights.I woke up the next morning lying on the bed, caressing myself through the tights and panties. I began to feel horny again, but I had to get up, shower, and go to work.While I was sitting at my desk, I began to think about being dressed in sexy lingerie and sucking cock. My phone started to ring, which broke my daydream. I answered the phone; it was one of my company's clients chasing a report I had promised to send them. As I spoke with the client, my mind repeatedly wandered back to my fantasy.
By the time the phone call ended I had made a decision. I was going to Suck a man’s Cock and swallow his cum. I didn’t care who it was but I knew I was going to make it happen.
Once I finished work I headed home with my mind set that I would try to find a man who would let me suck his Cock.
I was becoming aroused just thinking about finding someone and making arrangements to meet. I decided to search on the internet, but first I stripped out of my male clothes and took some more of my wife’s panties a Suspender belt and a pair of her Stockings. I chose a new pair of stockings still in their wrapper. I could buy another pair to replace them in the Drawer. I slipped into the panties and suspender belt and slipped on the stockings and attached them to the suspender belt with a little difficulty. But finally I managed it.
I then switched on the computer and opened the internet Browser. I sat looking at the screen not really knowing where to start. Then I had an idea. I knew Craigslist had a classified section for Personal adverts. I opened Craigslist and found the personal adverts section. I read several of peoples adverts mostly men searching for women. But also men looking for men section. I clicked to place a free advert. I said I was a First timer looking to Suck Cock and swallow cum. And I was willing to travel. I said I was nervous about it but I wanted to do it as it was my fantasy and I wanted it to come true. Once I was happy I clicked to place the advert.
I realised my cock was throbbing again and also leaking Pre-cum into my wife’s panties. Now all I could do was wait for a reply to my advert. I lay on the bed and masturbated again while thinking about sucking cock. Again I had a strong orgasm and pumped a large load of cum into some tissue. I lay on the bed and dosed off. I slept for about an hour. I woke up and went and got a drink. I then returned to the bedroom and noticed I had emails. I sat and opened my email. I had 6 new messages. I opened the first message it was a reply to my advert. It read You can suck my 7 inch cock if you want. I then read the others they were all very similar and none of them jumped off the monitor as being the one. I was happy to get replies but I wanted someone who sounded just rite to meet. So I switched off the computer and went downstairs to get something to eat. I would check my messages again later when I returned from visiting my wife in Hospital.
A couple of hours later I returned home and went straight to the Computer. I logged on and checked for any emails. I had 11 new messages waiting for me. I opened them one by one reading each one and trying to decide which I would reply to. The second message sounded promising from a man called Simon. He said he was an older man who lived alone and could accommodate and he would be glad to welcome me to visit him to see how we got on He also said he understood that as it was my first time I would be nervous. He said we could go at my pace and that there was no pressure from him if I changed my mind.
I replied immediately saying that I would like to meet him. I continued to read the rest of the messages and as I was my computer alerted me that I had another new message. I clicked on the message and it was John asking if I was free the next day to visit the next day. I replied that I was at about 3.30pm. If that was ok for him. He replied almost straight away saying Yes that was fine and sent me his address. My heart skipped a beat as I read the message. I knew the area where he lived well. Feeling excited I replied that I would see him tomorrow at 3.30pm.
Time seemed to drag. It felt like the time to meet would never arrive. I didn’t sleep well that night checking the time throughout the night. I was up early the next morning all I had on my mind was meeting John and finally sucking a Cock.
The day continued to pass slowly but eventually it was nearly time to leave to travel to Johns address. I sent him a short email saying I was on my way and would see him shortly. I got in my car feeling nervous but excited. I drove to his house and parked around the corner from it. I took a few deep breaths and got out of my car and walked down the road. In my head I was thinking what if I am being watched. If someone knows what I am going to do. I got to the house and knocked on the door. I had butterflies in my stomach as I waited for the door to be opened. It felt like forever but then the door was opened and I said are you John. Yes he replied come in. I stepped inside and he directed me down the hallway to a room at the rear of the house. Take a seat he said and indicated toward the Sofa. My heart was pounding in my chest as I sat down. John asked if I would like a drink of any sort. I said no thank you I am fine. He was quite attractive dressed in a t shirt and grey jogging bottoms. He said I have put some porn on the Tv to relax us. I looked at the Television and a naked girl was kissing a man’s cock and sucking on it. John sat next to me and as he did he pulled down his joggers to expose his hard Cock. I looked at it quickly it was about 7 inches fairly thick with a foreskin covering his cock head. He sat next to me his legs spread slowly masturbating. He didn’t look at me he just looked at the television. He then said go ahead touch it. I reached out my hand and held his hard cock in my hand. I was surprised how different it felt in my hand to my own cock. I could feel the warmth of it and it felt heavy in my hand. The skin was soft and velvety in my hand it seemed to be harder than my cock has ever been. I began to masturbate him pulling the skin back and forth so his shiney cock head was exposed. He lay his head on the back of the sofa and moaned. I had now relaxed and enjoying having his hard cock in my hand. He then said go ahead give it a kiss you know you want to. I leaned my head over and continued to masturbate his cock. As I got closer I could smell his manly but clean scent from his cock. I completely pulled back the foreskin and leaned in to kiss his cock. All I wanted now was to get his cock in my mouth. I kissed it and could taste his pre cum on my lips I licked the head of his cock and savoured the taste of it the feeling of his cock head on my tongue was incredible. I opened my mouth and let his cock slide into my mouth. Moaning as I sealed my lips around the head of his cock my tongue lashed and licked all around his throbbing cock. I began to Bob my head up and down on his cock loving having it in my mouth. I did this for a while and I felt his hand on the back of my head pressing down to get me to suck more of his cock into my into my mouth. John said oh yes that’s good keep doing that. Feeling encouraged I began to suck harder and Bob my head faster going deep into my mouth. I was loving the fact I had done it I was now a Cock sucker and loved it. Suddenly John started to moan and said I’m going to cum. My mouth was suddenly filled with fluid. I thought at first it was my saliva but as I lifted from his cock and the air got into my mouth I realised it was his cum. I could now taste it and I loved it. He held my head and said let me see. I tilted my head back and opened my mouth so he could see his pool of cum in my mouth. He then said quietly Swallow it. I did and felt it slide down my throat into my stomach. John the said. Good lad did you enjoy that? I said yes it was fantastic I loved it!! We straitened ourselves up and he said you did a good job for your first time. I said thanks. He then asked did I want to do it again sometime. I told him yes definitely. Good he said when do you want to come round again. I said could I come after work tomorrow. Ok he said what time. I said about 5.30pm. One great he said see you then. I drove home with the taste of his cum still in my mouth and the tingle it left on my tongue. I felt really pleased with myself and knew I wanted to suck many more cocks and swallow their cum. Little did I know I had begun my journey to becoming a Crossdressing Sissy Cock and Cum Slut. TBC….!!! |
