Written by theadventureman

Gay
24 Nov 2011


I had moved on from curious to experimenting. I started just chatting on the internet moving on to cam sex. After a couple of years of that I finally got the courage to actually try out cock. After all, I loved wanking and being rude on cam with guys. Why wouldn’t I enjoy it for real?

I started going over to scratch woods, late at night and see what fun I could have. Every time I went I would meet someone who would at least wank me off, once or twice I returned the favour. The whole discreet, naughty cock fun was so horny! After I usually felt quite shocked and disgusted with myself, but after a few weeks or so, I would start thinking about the next time.

One day over the woods I met an old guy, a very naughty/dirty old man; we went back to his and had some incredible fun. He was totally bottom and just wanted my cock. I met him several times over the next year, every time getting more adventurous. The first time I went there, he sucked me off and let me screw him. That was the very first time I fucked a man. By the time he moved away, I was going round his and spending 4 or 5 hours naked being very rude and crude, unless of course, he wanted me to wear something for him. he liked me in nylons and panties, and now and then he would put me over his knees and give me a gentle spanking. I discovered he liked me to piss on him and loved showing me use him, to others on web cam.

Unfortunately he left so I had to search for some new fun and adventures. Someone told me “gumtree” was a good place to look, so I tried. I was so surprised how many people were looking for the same sort of thing. One advert caught my eye in particular. A 38 year old bottom transvestite who could accommodate! I had never tried this but it certainly was on the list!

I arranged to meet “Tina” one afternoon. When I turned up I was surprised how different she was from her picture. It was her but not nearly as pretty. Not that it mattered, my cock was doing the thinking now.

She invited me in, and led me through to a bedroom. It was very untidy and as I sat on the bed, she picked some bits up. While she was bending over to do this, I had to look. She was wearing heels and black hold up stockings with a short black skirt and white blouse. During our previous chats, we both knew we liked role play, we agreed she would dress as secretary or school girl. she looked more like secretary at that moment.

As is often the case, when meeting strangers, the ice has to be broken. I thought I should take the lead. I asked “as a professional secretary, do you think this sort of mess is acceptable”?

She replied “no, I am sorry but I didn’t think you would show”.

“That is a very poor excuse and doesn’t make this acceptable. I don’t think I would be a very good manager if I didn’t do something”.

She stood up straight, turned around and looked at me “Please don’t sack me, I really need this job. My husband will go mad and we will loose our house!”

“I see, I said to her. I am sure if I were to use the formal procedure, you may be sacked”

“Please, I will do anything. Please don’t sack me!”

“Maybe there is a way. Obviously this is serious and you should be punished to make sure it doesn’t happen again, but I don’t want to sack you and you really don’t want that, do you?”

“No, not the sack, anything but that.”

I walked over to her and told her “go over to chair stand behind it and bend oer, placing your palms on the seat”.

She did this and asked “what are you going to do?”

I followed her over stood behind her, bent over the chair with her skirt rising to show off her white panties. I gently lifted the skirt, so she wouldn’t know, to get a better look. I told her “I think a spanking would improve your performance at work. I think that would be better than sacking you, wouldn’t it?”

She complained “you can’t do that, where is that in the company rules?”

After I explained it is this or the sack, she said she would accept what ever I had to do to make her behave better.

For the first few smacks I did it as she was, then I lifted her skirt exposing her clean white silk panties and shapely bum and carried on smacking. I was so tempted to pull those panties down round her knees an tan her bare arse, but resisted.

When her cheeks where nice and blush pink, I told her to stand up, as I thought that was sufficient.

I asked “do you have anything to say for yourself?”

She apologised, promised to be better and said she was indebted to me for not sacking her.

“Yes, I said to her, you could say I did you a favour. So I should ask what you want to do in return.”

“What do you mean; I thought the spanking was my punishment?”

“It was, I whispered, the punishment for this mess. I helped you not to get sacked. Maybe you could help me, just this once and that would be our secret too?”

She asked “what do you want me to do”

I moved closer and grabbed her hand and pressed it against the bulge in my trousers. The bulge, in my trousers, that had been there, since I lifted her skirt to smack her arse. She unzipped me and put her hand in, it felt so good I had to gasp, when she gripped my hard on, squeezing it gently like a pulse.

“do you want me to wank you off?” she asked

I told her I could do that myself and wanted something else.

“What do you want me to do then?”

“I can think of a couple of things, but I will let you decide” I whispered.

“I can’t have sex with you, I am married, she protested, I am married. I will use my mouth, but that is all.”

With that she knelt in front of me, undid, and pulled down my trousers. My cock was stiff, pointing straight up. she cupped my balls in both hands, this was good, then started to gently stroke up my shaft, stooping short of my bell end and sliding back down to my balls. She did this a few times, my cock was so hard the skin was tight and my bell end was totally exposed and swollen. Every time she stroked up my cock I had to groan, this was the nicest thing anyone had ever done to my cock, it was heavenly, I had to concentrate so hard, to make sure I didn’t cum!

After a few minutes of this, I was leaning back, holding the back of the chair behind me with my eyes closed and enjoying my hard cock being stroked by this stranger I just met. I felt a new sensation in my cock, the warmth and moist of her putting her mouth over my stiff swollen bell end. She slid her mouth down, swallowing about 4 or 5 inches. Then she took it from her mouth and looked at me. “ Do you like that?” she asked. “

Its fucking lovely, you’re going to make me cum” I replied.

With that she started licking my bell end like a lollypop, flicking her tongue all over it. it looked so sexy and felt even better. I was groaning out loud, telling her she had a cock sucking dirty mouth. She put my bell end in her mouth sucking and licking. My knees went all jelly and I hung on to the chair. She was sucking my bell end while stroking my cock and balls. I couldn’t hold on no more. I warned her, in case she didn’t want me to cum in her mouth, but she just kept going until I had emptied myself into her. She was in a frenzy making sure she got every last drop out of me and off of me too and didn’t stop till I was almost completely flaccid.

She stood up and wiped her mouth and asked, “Does that mean you are finished with me now, can I have a smoke and tidy myself before I go?”

I told her that would be fine, but I would go to the bathroom first and her after. When we had both used the bathroom we sat on the bed, each rolling and sharing a smoke. I told her that she had given me the best blow job I had ever had. I also asked her what her husband would say, if he knew that she had been sucking her bosses cock and eating his spunk. She looked a bit surprised.

I placed a hand just above her knee and I told her not to worry as he would never find out. At the same time I was saying this I was slowly sliding my hand up the inside of her thigh. She asked me what I meant and if I was going to tell?

“well, I said, lets just say, If you keep me happy and do what I want, I am sure no one will have to know. I think you’re very sexy and I know your other secret too!” by this time I had sled my hand up her thigh, over the stocking tops, along the panty line and now I had my hand on the front of her panties. She pushed my hand away and rolled over onto her front. As she did, I followed. I was now on top of her, her waist under me between my knees. I shuffled down until our hips were level. I leant forward and on top with most of my weight on her and put my mouth close to her ear to whisper. “I am going to take off your panties and make you nice and slippery between your legs, and then I am going to fuck you. While I am fucking you I am going to have my hands in the front of your panties and if you resist in anyway. I will tell your husband that you are the office whore who sucked my cock”.

“Please, no not that” she said as she squirmed; only stopping, when I reminded her that I would tell on her.

I got up and moved to the bottom of the bed, taking hold of her ankles, I parted her legs as wide as possible. As I knelt between her legs I could see right up to her panties. I placed my hands on her calf’s slowly caressing her legs as I worked my way up. I lifted he skirt above her waist and got down to press my stiff cock between her bum cheeks, through her panties. I pressed and grinded for a few minutes, telling her how good she felt and how I was going to enjoy what I was about to do to her.

I got up and told her to get on her hands and knees, she did immediately. I pulled her panties down to her knees exposing her fuck hole. I could also see that this dirty bitch was enjoying it as much as me. I had a feel of her bum; nice, smooth and not a hair in sight, I stroked between the cheeks brushing over her hole, and this made her groan. I squeezed the lube onto my fingers and started to smear a generous amount between her cheeks, concentrating on her hole, by now she was moaning and squirming, more so when I slipped a finger in. before long I had 3 of my fingers in her, which to my judgement and eagerness, is ready for something else.i put a durex on myself and gave it a good smear of the KY, and asked her “do you know what I am going to do to you now, you dirty slut?”

She replied, in a kind of quite and half keen voice “are you going to fuck me?”

A gave her the answer straight away, forcing my bell end into her tight hole. She was really groaning now, and when I slowed down she would moan for more or don’t stop now. I didn’t need much encouragement and slowly pushed my cock in as far as I thought it would go, then let it slip all the way out again. I did this a few times pushing faster and deeper everytime. She was still pleading for more, so a started to fuck her faster and harder, one arm on her back the other wrapped round feeling her semi hard cock. I felt so fucking horny right at that moment; I couldn’t help but shoot my load within a few minutes.

When I pulled out of the dirty bitch, she jury collapsed on the bed and rolled up, as if she had a belly ache. I asked if she was ok, and she replied “I am glad we did that, and I promise, whenever you want to you can do that again, as long as my hibby never finds out.

We sat down and had another smoke, then I had to go. We did meet a few times after that and played policeman/shoplifter (who had to be searched), headmaster/pupil and a few other things, but nothing ever matched that first time.

Out of the blue he told me we couldn’t do this anymore as he had met a girl and was going to take it serious, more the shame!


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