This story continues a diary about my work in shop security with my straight friend Adam. The shop sold clothes and toiletries, both types of goods were popular with thieves of all ages. Normally we detained people in a security room adjacent to our observation office. The "obs" room had our cctv screens and data recorders were we could monitor the shop's ceiling mounted cameras and ensure images were being recorded.
When we had caught a shoplifter, we escorted them to our security room. This was a small office only about 2.5 metres square.
My name is Dave. I'm 33, tall (ish), just under 6 foot and slim. I'm also gay and love younger guys from 18 to mid-20's. Sadly Adam is straight, married and has a baby, he is right up my street: 25, slim very hairy chest and arms. Sadly I've never been able to see more of him but he knows I'm attracted to him. He's great about it, he is so confident in his heterosexuality that he is not in the least phased by my admiration.
I've wanted to tell you about Mike for a while. I'd met him some time before, we had a little affair but like so many he left the area. One afternoon in the shop Adam and I were watching the cctv, the shop was really quiet and most of the floor staff were simply tidying the clothes racks. I'd not seen Mike for about 5 years, he would now be 27, when a familiar face appeared on the cctv, it was him.
I told Adam that an ex-fuckbuddy had come into the shop. He wanted to play a "let me spot who it is" game but I just wanted to go out onto the floor and say hello. Adam suggested I go out and bring him back to the obs room to catch up, so I popped out to greet him. When Mike saw me he was happy and wanted to say hello. I told him I was working in the store but he could come back with me to the cctv room and say hello to Adam.
Back in the cctv room I introduced Mike and Adam who immediately sensed that the two of us had a sexual tension. Over a coffee Adam asked Mike how he & I had met. Mike became quiet with embarrassment and I said nothing. Adam pressed again and Mike looked at me. I told him that Adam and I knew more about each other than anyone ought to know and that if he wanted to tell the story he could.
Adam made another coffee and Mike started to tell the tale. He was living in a squat with his straight friend and supplemented his state benefits with begging. He had been working the local theatre entrance, sitting on the pavement asking people for spare change. One evening I was going to the theatre and saw him there. Although he was warmly dressed for the autumn weather I could see that he was a very tall slim young guy and he looked clean and looked after. Making a mental note I went into the theatre.
The next evening I went into town again and Mike was begging there again. The performance was due to start in about 15 minutes so I thought how best to approach him. At this point I knew nothing about him. I needed to let him know what I wanted but not to put myself at risk so I sat on a nearby bench and wrote a note. "Do you have sex with men for cash?" I wrapped a tip in the note, dropped it into his lap and went back to the bench about 30 feet away.
Mike looked up to see where the note had come from; when he looked over to me I gave him a nod. He waved me over. I felt safe as there were still people entering the theatre.
"Wait until the show starts, I'll come over to you" he said. I went back to the bench and waited for a few minutes. Soon the theatregoers had all entered and the doors closed. Mike came over to me, sat at the other end of the bench and asked me what I wanted to do.
He did not mention money and said that he was interested but very inexperienced. He told me his name and I introduced myself as Dave and asked him if he wanted to come back to my place.
He said "yes".
Back home I made us both a tea and asked him what he had previously done with men. He told me that he had jacked off with a friend from school when he was 15 or 16 but that was all. He then told me that he would try other things with me as he needed money. Again no sum was mentioned. After drinking the tea I led him by the hand as we went upstairs.
In the bedroom I pulled him towards me, he leaned forward and I kissed him. His lips were closed but when I kissed him a second time he opened to me. He was a gentle kisser, our tongues intertwined and it was a few minutes before we came up for air. Mike was wearing many layers of clothing to keep out the cold. First I removed his thick winter pullover and found a hoodie underneath; I took that off and found a t-shirt which I assumed to be all that was left.
When I slid my hands under it, expecting flesh, I found that he was also wearing a thermal vest! We both laughed as he knew what I was thinking about all the layers. He raised his arms up and took off the t-shirt and vest together. His slim smooth body was beautiful. He had pale skin that looked like it had never seen the sun. I could see his ribs underneath and his little brown nipples were just standing to attention. When I stroked his chest and nipples his chest swelled and he moved like a petted cat.
After a little more kissing and stroking I decided that he should get naked. I still had all my clothes on but I slipped off my shoes and Mike did the same. I dropped my hands to his jeans and started to open the waist and buttons. Once open they fell to his knees revealing long smooth thighs. Mike was 6'4" and I could see that his height was all in his legs. He quickly bent down and kicked his jeans off and lost his thick woollen socks at the same time. He was now stood only in his boxers. I was surprised as Mike then took the initiative; he pulled me too him and started kissing again: this boy obviously enjoyed kissing.
Mike now started to strip off my clothes too. Soon I was also down to my boxers. I gently manoeuvred him to the bed side; we sat together and then laid down still kissing. I let my hands wander down to his boxers and felt over the material. I caressed Mike's ass and he laughed a little.
"No one has ever touched my bum before". He said it with nervousness in his voice. I think that like most "sort of" straight guys, they only think that gay sex is no more than anal sex.
"Relax," I reassured him "we will only do what we both want to do together". He smiled and I just gave him a little peck on the lips.
Moving my hand to the front of his boxers I was in for a lovely surprise. He was as hard as they come. I felt it through the material and felt it all over and the little nuggets underneath. He liked that as I could feel it pulse and jerk as I held it.
"Time to lose our shorts" I said. We pulled them off together and kicked them off the bed. His pubic hair grew only above his cock, nothing on the balls and his cock was beautiful. He had a solid slender cylinder of flesh; absolutely straight, no upward curve, no bulges or tapering and the head was the same diameter. Uncut with his skin fully back he measured 8.5" slender inches. I was not going to let him fuck me that night but I was looking forward to it gently slipping into my hole at some time in the future. His balls were on the small side but looked proportionate as they were hanging low. I decided on some gentle oral administration.
Mike smiled as I started to give him one of my better blow-jobs. First I just took the head and ran my tongue around the piss hole and his foreskin. The skin was loose and there was plenty of it. I love to have a good chew on a meaty foreskin and Mike was just about crawling up the walls within minutes.
"Please, stop, or I'll cum. I don't want to cum yet. I just thought that gay sex was just going to be me giving you a blow job". I stopped for a little while and Mike asked if I would like the same.
"Yes, that's what I want. Whatever I do to you today, I'd love you to do to me." He got straight to work but was a little hesitant. "You ok doing this?" I asked. "Yes," he replied "but I am very inexperienced". "Ok, just take it easy and take your time. There's no need to rush. Just use your lips and tongue on me exactly how you want me to do you in 5 minutes". He smiled and got to work. He may not have done it much before but he certainly knew what he liked and was much more enthusiastic. After a few minutes I was getting worked up and stopped him. I asked him if he wanted me to suck him more. We swapped places. Mike had shown me what he liked so I concentrated on his piss slit and got my tongue deep into his foreskin. Soon he was groaning and thrusting gently. I told him to stop me before he came; soon he pulled me of him but his cock was rock hard, oozing and twitching. He'd pulled up very short. After taking a few minutes to kiss and stroke each other he started to suck me again.
I pulled him off me too, before I shot my load and asked him how much experience he had. He blushed and went quiet. I pressed again and he told me that he thought he was bisexual and although he had jacked off with a boy at school he had never had gay sex like this. I suggested he was a "gay virgin". He blushed again and agreed but asserted he had touched the other boy. I smiled and suggested he might like to try more than sucking. He became tense as he thought I just wanted to fuck him. I told him that I wanted to give him pleasure, not fear, to relax and that I was going to give him a massage. I don't think his straight sex experience was very broad either.
I got him face down on the bed with three pillows: one under his shoulders and head for him to cuddle and two together under his hips to raise his ass. I told him it was more comfortable to have his hips raised! Little did he realise was that it presented that desirable place. By the bedside I had some soothing massage oil. I straddled Mike's slim waist and squirted some oil onto his shoulders. It was cold and he giggled a little. Slowly I stroked it into his neck and shoulders. Mike purred as I did his neck, I leaned forward and licked it gently, he tried to look over his shoulder to kiss but I held him down and just nibbled his neck and massaged his shoulders. I continued to massage his smooth back. He had some slender muscles on his back and he kept wriggling slightly as I did him. His smooth skin was so soft to touch and I loved just stroking and touching him. All the time he got more and more relaxed. I kept moving down to his waist and sat on his thighs; his ass was there in front of me but I decided not to go there yet other than to just spread the oil over his cheeks. Soon, sat on his calves, I was massaging his thighs up to his bum as I was going deep into the smooth flesh it was moving gently and I was able to part his cheeks and just glimpse at that virgin hole. I could just see that like the rest of him there was no hair and it looked absolutely pristine. Mike had no idea that I could see his most intimate of places and he just continued to relax as I worked his thighs. Finally I got down to his calves and feet. I gave him a good 10 minutes down there and he loved it, especially as I played with his toes. I am pretty good at feet and kept them very wet with oil, afterwards he asked me if I was shrimping him. As it happens I was not but if he thought that then let's not disappoint him. He thought I had finished massaging him and he started to turn over.
"Would you like me to do you now?" he asked. There was no way I was going to refuse and we swapped positions. Although his technique was naïve he was very caring and thorough. He also spent some time massaging my bum-cheeks and I am sure I felt him stroke close to my hole but he did not go over it or try to enter.
Following our massage, we kissed and fondled a lot more. I asked Mike if he would like me to continue and finish his massage. Mike looked quizzical but rolled over onto his stomach again. This time I made sure that the pillows were well under his tummy and that his ass was raised. This time I started on his thighs and worked upwards my thumbs were massaging firmly into to tops of his thighs, as I pulled at his bum cheeks his hole became more visible. I was sure that his cock was hard so I gently reached underneath him and pulled it back so that it was supported by the pillows and pointing down. Now I spread his long slim legs and everything was in view. His slim 8.5" cock with its foreskin drawn right back; his smooth balls were not as low hanging as they had been but I was able to move and play with them easily, his smooth taint just shone with oil and led me to his glorious virgin hole.
At first I massaged his bum and let those smooth cheeks just role together in my hands. At one point I knelt right down towards his cock head, spread his cheeks wide and breathed with my hot breath directly onto the back of his cock. I gently licked up and down the shaft and head and then sucked it up into my mouth just taking the head and what I could of his foreskin. After only a couple of minutes I could taste his pre-cum. Just as I expected it was salty but sweet. I told him that I could taste him and he said that he was surprised as he generally did not produce pre-cum. He seemed happy that he had and was getting quite worked up. Next I moved up to his balls and taint. I enjoyed getting one ball in my mouth and pulling gently, stretching it away from his body. Mike started to squirm a little and I eased off. I did not want him to stop me as I was so close to my goal. I finished off on his balls and ate his taint.
I had to part his cheeks now to get at his taint, I could feel the root of his cock underneath it and I licked, nibbled and bit at it. Mike was groaning loudly and squirming. What was different about his squirming was that he was not trying to get away but push back onto my mouth. I knew he was going to really enjoy my next course on the menu. I told Mike that there was just one more thing for me to do and to lay still. By now he was floating on cloud nine and I was ready to push him further. All the time I was holding his ass apart and for some time I had a great view of his beautiful virgin hole. I decided on a slow approach and started to lick the insides of his cheeks, either side of his hole. Again there was no hair at all; it was smooth and soft skin. Each lick got closer and closer until Mike pushed back onto my mouth and my tongue brushed firmly over his hole. Mike's reaction was what I had expected. He pushed back more and more and I was happy to let him use my tongue. I am unsure what he knew was happening and within two minutes Mike's ass was starting to open. He had no thoughts of guarding that virgin hole from me, he was so wound up in the sensation he was happy for me to fuck his hole with my tongue. I firmed it up and started to push into him. I could hear Mike now gasping with pleasure.
As his pleasure level rose so I began to handle his ass more firmly. I used my thumbs to pry him open and they were touching the outsides of his pink opening. My tongue doing more and more inside that wonderful place I continued to pull and gently stretch him. Soon he was wide and I told him to let me play with him some more. I told him that I was going to make him feel even better and that I was not going to spoil things by trying to fuck him. I told him his ass was safe but there was more he could enjoy if he let me continue.
"Please do more" he said very simply. I decided I needed a brief rest and moved up the bed to kiss him. Mike ate my face off, biting at my lips and chin; hr then begged me to do more down there. I told him that I was going to "eat his bottom"; that became a phrase that we used together. There were so many times in the future when one or the other of us would ask: "Please, eat my bottom".
After a couple of minutes rest, I moved back down the bed to my new dining room and Mike offered me a main course of ass. He was still quite open and he relaxed even more when I started to "eat" him. Now I was holding his hole open with my thumbs while licking vertically with my tongue in big, firm strokes. Mike started to talk but he was making no sense. Just odd words were coming out of him: "Please, more, oh, yes. Hole, eat, take my ass. Hard firm lick, more." I now knew that I could do anything I wanted to Mike but decided that although he would be unable to stop me from fucking him, now was really not the time. I wanted him to have the time of his life and have no regrets. If he was enjoying this as much as I could see, there was going to be a lot more to come and he would have no hang-ups about his ass. He now knew what immense pleasure he could have with it.
I now rolled him over onto his back and checked out his cock. He had completely lost his erection while I was eating his bottom. He told me afterwards that for the first time ever he had enjoyed sex and not had an orgasm. I challenged his view about not having had an orgasm and told him that he had had an anal orgasm. Mike thought about it. One funny thing about Mike was you could see what he was thinking by his very open face. Soon he laughed and told me that he felt so good when I was eating his bottom, it was as if his cock did not matter. I told him that if he was into his ass (knowing that to be the case) that he would learn to have fun and orgasms in many ways and that did not always mean shooting spunk out of his cock. This was so new to him I thought he was going to say "no" until his brain kicked in and he remembered what he had done the last hour.
Now I suggested that we both come and shoot out spunk together. Mike's cock was still soft even though mine was just about going purple. "Before we do, can I do something for you?" Mike asked. Naturally I nodded. Mike turned me over onto my face and pulled my legs apart. For the first time I knew he was looking at my hole. "Dave, I'm not sure what to do but can I try and eat your bottom like you did mine?" there was no way I was going to say "no" so I just relaxed. "How do you know to trust me not to hurt you?"
"You trusted me and now I trust you" we had just given each other a lot of pleasure, I knew that Mike was going to try his best to make me happy. He copied what I had done, he licked, nibbled, tongue fucked stretched, spat on it and licked even more. All the time his thumbs and fingers were stretching and pressing, opening more and more.
"Your bottom has opened really wide" Mike said with some amazement, "did mine do this?" I knew my hole would be open. "When yours was open I would have been able to put a 50 pence piece over it and still seen pink at the edges. Mike blushed absolutely scarlet when he realised how he had been.
"Please, shall we come?" with an invitation like that, here was no way I was going to turn him down.
"How do you want to come?" I asked. "Kiss me and play with me while I play with you too." he replied. So we laid together and started to wank each other's cock. I had decided that his spunk was not going to waste. Soon I shot my load over my abs and chest. Mike liked to watch me shoot and he was soon edging close. I moved down close to his cock and as his head started to swell I closed my lips over it and took every drop he shot out. Mike screamed with pleasure, his eyes were closed and his face was screwed up. I did not bother to count the shots I could feel, I just became more aware of my mouth feeling fuller so I decided to swallow. After he had finished coming I moved back up to him and kissed him. As soon as he tasted his own cum he backed away.
"What's wrong" I asked: he was shocked by the taste. He had never tasted his cum before so I told him to kiss me again. He was reticent and kept his mouth closed. I told him to stop being silly and kiss me properly, if I could swallow it, he could taste it. He smiled and kissed me gently opening his lips narrowly. I kissed him firmly but only ran my tongue around his lips not inside his mouth. Mike pulled me very close to him and hugged me tight. I could see tears in his eyes and not wishing to embarrass him I said that we should have a shower and get rid of the oil.
Our shower together was brotherly, just washing the oil off and gently admiring each other's body. We dressed and Mike suggested he ought to go but then went quiet. We had started this as a business arrangement but not spoken of money at all.
I told Mike that I did not know anything about him or his money and what he thought was the best thing to do. He said that he had never done this before and didn't think he liked the idea of taking money for sex. I told him that he was so much more than that, but some money might be useful to him. He said that he was going shopping tomorrow for groceries. I offered to pay for his groceries and we settled at that.
Before we parted for the night, Mike asked if we could meet again. I told him that I would love to see him again and gave him my phone number. "Dave, I've had a brilliant time and I have never had such good sex with anyone before. I'm not sure if I'm bisexual or what but I want to see you again soon." There were tears in his eyes when he spoke. I held his face in my hands, wiped the tears from his face with my thumbs, kissed him gently and told him to ring me any time he wanted.
Adam had been listening to this entire story. As he moved away from the table I could see a tell-tale bulge in his trousers. So he was turned on by gay stories, perhaps there is some fun to be had here too. D A Bishop