Finally scratching that itch

(Part 1 from 1)

I've always been an introvert. I never want the spot light and that has led to me missing out on many things that I have wanted to experience. For example, I had crush on a friend's mother. She was plus sized and considered unattractive by most, but I loved the feel of her soft body when she hugged me. I masturbated and had many wet dreams involving her. I would meet a girl who could have been her twin, but because I feared being involved with someone unattractive, I denied her advances.

I never liked talk shows, but one day I came across an episode where men dressing like women was the topic. Some were obvious males while others could fool you. What was interesting was I found myself being attracted to the ones that could fool you, despite knowing they were men. As men were fooled, they'd have it revealed on the show that they actually slept with a man. I began to fantasize what I would do if I were ever in that predicament. I've had my dick sucked many of times before officially confirming it was a woman. In other words, woman have jerked or sucked me off before I had access to their vagina. But what I was really interested in was what I would do after discovering they were a man. Would I continue? I would have already been enjoying it, so why put and abrupt end to the fun?

My fantasies became dominated by that and one night returning from a strip club, I passed an alternative club where a nice looking plus sized she male hit on me. I was totally aroused and even exchanged numbers. We spoke once on the phone and I showed little interest in the convocation as hooking up with her could have become reality and I was scared what would happen if I liked sleeping with her and what that meant.

A final example of how I prevented myself from a possible enjoyable experience was when I was hit on by a man at the gym. I've always had issues with the size of my penis. I m average, but at the time I didn't only seen porno dicks and I knew I wasn't that big. One day while out, I had to use the restroom and a workout facility was the only option. Their restroom was in the shower area and because I wasn't a member, I should t have had access. However, the young lady allowed me to use it. A grown man came out of the shower as I entered and what I became fixated on was the size of his dick. He was very small. I m sure the shower made it smaller, but his dick was definitely smaller than mine. That turned me on. After using the restroom I would pass him again. His tiny dick and sagging balls were all I could look at. It reminded me of the Greek statues. It was beauty in it.

Years later, while working out I noticed a man looking at me as I lotioned up after a workout. I had often used shower times to check out the packages of random men. I also loved walking around nude when noticing I was larger or the same size as many of the others that were naked. I decided to give the onlookers a show making sure to rub lotion on my crotch while he was looking. As we were semi isolated, I damn near masturbated for him. As I left out and was headed to the parking lot, he approached me. I played dumb and he lost interest and his nerve as another opportunity was blown.

I could go on and on about similar chances I've blown, but eventually I broke the trend. We have a local magazine and on the final pages their are adds for phone sex, massages and the like. I read them for the entertainment and stumbled upon a married couple that did full service massages. I knew full service meant happy ending as I'd entertained the thought of getting a male to male rub down but always refused to make the call. But a male and female team was right up my alley.

Including a female meant I eased the fears of it being a gay experience. The couple labeled themselves as mature so it meant I wouldn't know them and they wouldn't t know any of my friends. Upon calling, they were an hour away so having this experiment be my secret was helping me make the decision to go with it.

As I drove over, I focused on what the man would look like and what he would want to do to me? What would I allow him to do to me? I had a few things I wouldn't do. He could not penetrate me and I wouldn't penetrate him. That s odd as I've had many women fuck me with vibrators, anal beads and their fingers and I really enjoy being fucked in my ass. But a man doing it with his rod was not something that interested me. Kissing was another no He could suck my dick, but I would only suck or touch his penis if he was my size or smaller. A man with a big dick did nothing for me.

As I arrived at their condo, he answered the door. He was tall and probably of German ancestry. He was sort of balding and had a receding hairline. I d guess most women wouldn't t find him attractive. He was just what I wanted.

After brief conversation, I was told to undress and get on the table and he and his wife would be down. I had forgotten all about her. I finally began to wonder what she looked like. The add said mature, bushy, as in a hairy pussy, and 36 dd or some number like that to point out she had natural big tits. I thought model type when initially reading it, but after getting a look at him I figured she would look different. In reality, it didn't t matter. Especially if he had a small unit. That was the deal breaker. What he was working with.

When they came down the stairs I first noticed his cock. He wasn't hard and it looked to be the same size as mine if not smaller. I was happy! His wife had large breast as advertised. He looked to be in his mid fifties and she looked older than him in the face. She was chubby but her breast sort of evened out her frame. I found her unattractive and it turned me on. I was fulfilling a dirty fantasy and had the perfect dirty looking playmates.

It began as a normal massage, except we were all naked. He did my feet while she did my actual head. Every once and a while his dick would brush against my feet. I believe he was doing it on purpose. As he rubbed my lower legs and moved north he would constantly ask if I were ok. I always assured him to continue. I was rock hard at this point. My dick was jumping on its own. Her large breast were just above my head but I was concentrating on his still phallic penis. As his wife moved to me chest area he d reached my thighs. He commented to his wife that I had a nice piece. I was stunned at how natural it all seemed. When I closed my eyes I couldn't t tell which had were the man's and which were female. They were using baby oil and their hands across my naked body was great. When his dick touched me, I didn't t die. There was no major tragedy. I was really enjoying myself!

I was so pleased that when he rubbed high on my thighs I would let out moans. I was wanting for my dick to be touched badly at the moment. After more incidents of his dick touching my hand, as they we both on my sides, he continued to ask if I were ok. I assured him I was. They knew I was loving it at that moment.

He had encouraged me to touch his wife as they rubbed me. I sucked her breast for a moment and ran my fingers through her pussy hair but that wasn't t what interested me at the moment. I was turned in by how soft and silky her skin felt. As his dick brushed against my hand again, that got me to look in his direction. I wanted for him to have an erection. He didn't. I began to debate with myself. I wanted to stroke him to see if I could get him up. I wondered what his dick would feel like in my hand. They had reached the point where there was only one part of my body that they hadn't t touched with my being on my back. He placed his fingers on my cock and gently stroked. I moaned. He knew he didn't t have to ask if I were ok anymore. His wife just looked on as he began to grip my cock and stroke it with his baby oiled hands. It had me feeling so relaxed and comfortable. Without thinking, I began to stroke his cock as he made small talk to his wife. He was telling her to go prepare the warm towels as we stroked each other. He never became erect although I did feel the sticky ore cum escape from his dick. His wife was out of the room and I decided to go for it.

I placed his tiny member in my mouth. If I had to explain how it felt I would say imagine a balloon shaped like a dick. As I sucked it seemed soft and hollow. He never became erect as I sucked and began to bobbing as I find led his scrotum sack. I asked if he would get hard and he told me he and his wife went at it before I arrived so he probably wouldn't t be able to get it up. His wife returned and he went back to jerking me off as I lay there and enjoyed it allowing more and more moans to escape.

He announced I was really going to like what happened next. Both he and his wife rubbed my lower stomach simultaneously. They played in my pubic hair and rubbed my balls. On began to stroke while the other played with my sack. I grunted aloud for all to hear. I bust my impressive load and they had to jump back from getting sprayed. He got back to work right away milking all of that nut out of my dick. He commented to his wife how I had put out a lot. She was still amused from my eruption but eventually got back in on the action.
They cleaned me off and turned me over and he pretty much did the rest of the massage on his own. I told myself it was going to be a one time experience but I was contemplating that as I got my back rubbed. I wanted to have my ass played with. I wanted to experience sucking his rock hard dick. I wanted to suck my cum from off the breast of his wife.

The hour long experience came to an end. I left thinking g I would have to come one or maybe two more times.

I've been back many more times! I've yet to see him with an erection. His age makes me think erection dysfunction. But as I've entered the swinger's lifestyle with my girlfriend, I've learned some men are just turned on by many different things. Maybe his thing is getting men off with his wife. Whatever it is, I enjoy being part of it. It s my dirty little secret, albeit I just shared it to anyone that reads this.

Pages : 1 | More First_Time_Stories, check also erotic stories or adult stories.
Post your review/reply.

Allow us to process your personal data?