Sissy giving head

Single bi mature (55) male into a variety of things. I’m masculine and average looking, but love the feel of lingerie on my body. It simply turns me on to have silk, satin, and lace on. I’m certainly not a passable cross dresser but enjoy the feel. I am clean shaven, discrete, a non smoker and ddf. I expect the same in a partner. My cock is small, my balls are large. I am cut. I enjoy fondling, porn, nudity, oral, mutual masturbation, and erotic photography, and other things possibly. I would like to meet someone who can be loyal to me while we are in a relationship. I feel that reduces the risk of sexually transmitted diseases. I do enjoy small cocks on other men and uncut is a plus. I think I have foreskin envy. I large cock will not rule you out though. If you are a male or female who thinks we might fit, no pun intended, please contact me.

I really didn’t think I would get a response. But low and behold I did about a week after the ad was placed I got an email from Seredipity55. I couldn’t tell from the name whether this was a male or female. The message said:

Saw your ad and it does look interesting. Have you had very much experience with other men and women? What are your main interests besides sex? We like to get to know someone before we get too involved. We are a couple by the way, both bi and open to a number of activities. We too are average looking although I would say Janice is pretty, she thinks of herself as average. I am Pete by the way. I am 5’10“, 180 pounds, also clean shaven and bi. I would say that my cock is average, but it is uncut. It is about 6“ erect. Janice is 5’3”, 125 pounds and has short dark hair and small breasts. She is shaven also. We both hate to get hair between our teeth when we have sex :-). We are both in our late 40s.
She has really wanted to watch while I had sex with another guy and as we have discussed it, it has become very inviting to me as well.
Please respond if we sound interesting to you.
Pete and Janice

Wow, does a bear shit in the woods. Yes, they sounded interesting. I could hardly contain myself as I composed a reply, my penis stiffening and throbbing just thinking about getting with a couple. This is too good to be true, there must be a catch. Would they be completely off their rockers, ugly, what? All I could do is follow through and find out.

My response was measured. I didn’t want them to think I was a complete lecher even if I was. I mentioned that I enjoyed reading, mainly fiction, out door activities such as walking, hiking, and backpacking, watching movies, or dvds, and traveling. I also mentioned that I was divorced and had no children. Also the fact that I graduated from college with a business degree and was employed as a mid level professional, whatever, that is it pretty well defined me.

We corresponded back and forth for a couple of weeks, getting to know each others likes and dislikes, and becoming more comfortable with each other. Finally, they suggested we meet face to face for a drink. I had not suggested it yet because we both mentioned we didn’t like pushy people. We decided to meet at the Rusty Nail on we 151st Street on Friday evening around 7:00. We gave a description of what we would be wearing.

I was nervous as a long tailed cat in a room full of rocking chairs as I made my way into the bar and grill Friday evening. I hoped I would make a good impression and I hoped very much that they weren’t wackoos. Our voters had passed a law against smoking in public places a few years back so it was quite pleasant to go into bar with friends and socialize, as long as the music wasn’t blaring so loud you couldn’t think. This bar and grill had a neighborhood feel to it and good food as well as reasonably priced drinks.

I spotted Pete and Janice almost immediately in a booth towards the back of the bar. I went down and introduced myself.

Pete said, “Hi Bob, good to meet you in person finally.”

I agreed and we sat and ordered drinks from a perky waitress who was all smiles. It was slightly awkward since we had pretty much gotten to know our likes and dislikes on line. We made small talk while waiting for the drinks to arrive. I maintained eye contact as we chatted. Pete had been pretty accurate in his description. He was average, but nice, looking and average height and weight. He had dark hair, and brown eyes. Janice was not a knock out beauty but she was certainly pretty. She had a oval face with a smooth complexion, and shoulder length dark hair and a pair of emerald green eyes that I found it hard not to stare into. She was of average height and build, and I could tell she was fairly small in the breast category, but that was fine with me. I love small breasted ladies.

We finally got into the routine of conversation, cussing and discussing everything from the local NFL teams chances this fall to the economy, jobs, cost of living. Finally about 10:00 they said they needed to run and would be in touch. I didn’t know where things stood. I couldn’t tell whether they liked me or not. I knew they would be a fun couple to play with if they did. I guess I’ll just have to wait and see what happens.

Finally on Sunday night I had an email from them. They said they were sorry they hadn’t been more committal, but they wanted to talk things over together before they made any decisions. They said they were very pleased with out meeting and thought we could all fit well together.

I wrote them back and thanked them for the note and said that I felt the same way. I understood that this was a big decision on their part and that I felt the same way they did. After a couple more emails back and forth, we decided they would come over to my place Friday evening for supper and no telling what else.

Needless to say I was a nervous wreck all week. I cleaned and cleaned until the house sparkled and planned a shrimp and pasta dish that usually got grave reviews. I stocked up on wine and beer and rented a couple of porn flicks from the video store. I even put candles on the table in case we needed them and found some soft music CDs to play. I also stocked up on condoms, not knowing what might be needed.

Finally the hour arrived. Pete and Janice showed up on time with nervous smiles on their faces. I ushered them into the kitchen and asked what they would like to drink. I gave them a choice of iced tea, coffee, wine or beer. Janice accepted a glass of wine and Pete opted for a beer, as did I. I suggested we go out on the back deck since it was such a lovely evening. I had put a lot of work into my back yard. It was well landscaped to offer a lot of privacy and I had a water garden near the deck that provided a relaxing water sound to go with the pleasant temperature. We sat and chatted for awhile on he deck before I went in to fix supper. It didn’t take long since I had already made the shrimp and tomato sauce mix for the spaghetti and had the salad ready. All I had to do was boil the pasta and toast the garlic bread. I quickly had it all ready and called them in to eat. I didn’t light the candles. I thought that might be a little too much.

After dinner I quickly cleaned the table and put everything into the dish washer. It was dusk and we retired to the family room where I had a large screen high definition television. I asked if they would like to watch a porn flick and they quickly accepted, as they sat side by side on my large leather couch. I noticed they had left a place for me next to Janice. I found one I had specifically picked for the occasion. It was a flick that had two men and a woman enjoying all kinds of activities.

I inserted the dvd and started it with the remote while moving over to the couch to sit beside Janice. I sat and we all became engrossed in the activities on the screen. Two guys and a gal were completely going at it, and sometimes one of the guys would slip out of her cunt and end up in the other guys mouth. It was completely erotic and a real turn on for all of us. My cock was stiffening by the minute as I watched the video. All of the sudden I felt a hand on my lap. Janice was rubbing both my crouch and Pete’s. Wow, what a turn on. Of course we were all still a little uptight about the whole situation. I wasn’t sure what moves to make. Finally Janice jumped up and yelled, “Fuck, we know what we want. Let’s quit being so prudish“, and she started to strip. Pete and I watched her as she stripped completely naked. I was in awe. She was gorgeous. Her body was superb and those B size breasts were fantastic as I glued my eyes to her stiff nipples, and her smooth shaved pussy.

Oh my God, I thought as I jumped up and frantically started stripping off my clothes as well. Pete, not to be out done, did the same and we all came together. Three naked bodies fondling and groping with unrestrained action.

I kissed Janice and she kissed me back and Pete was behind her, I’m sure his cock was raging hard and pressing between her butt cheeks. My 5“ cock was throbbing non-stop and pressing against her vulva. I could feel the wetness of her pussy as I lifted her and let her slide back down onto my throbbing cock. Pete moved back and let me lower her to the floor and I began to move my hard throbbing cock in and out of her slippery tunnel. Suddenly I felt something on my butt. It was Pete. He was fondling my butt as I fucked his lovely wife. Janice’s wet pussy was like a silk glove on my cock as I pumped my rigid 5“ cock in and out of her. I kept thinking of everything I could to take my mind off my cock which I was afraid was going to erupt much too quickly. I could see Janice biting her lower lip as she concentrated on my cock rubbing the inside of her cunt. I felt Pete’s cock now between my butt cheeks. It was hard and dripping with precum. I told him to move around so Janice and I could suck on it. He did so and she and I took turns taking his rigid, throbbing tool between our lips. It felt strange sucking on a cock, but it was a great turn-on. We were all so turned on and excited it didn’t take long for a chain reaction to occur. I felt Janice convulse and push her pubic mound into mine as I felt Pete’s cock begin to spurt hot cum into my mouth. All of this set me off and I shot my sperm into Janice’s pussy, pushing as hard as I could.

We all fell on the floor exhausted from the activity and caught our breathes. Finally, after a few minutes I said, “Wow.” We all laughed.

What fun it had been, but it was too fast and too hurried. We all knew we wanted more but this time a measured and relaxed enjoyable activity. I suggested we retire to the bedroom where I had a smaller but just as good television that we could watch the movies on.

We entered the bedroom and Janice pulled back the covers as I turned on some soft music. Janice suggested that I put on some lingerie and see what that would do for us. I readily agreed and went to my lingerie drawer to find what I had, while she ran out to get her bra and panties from the living room. Just the thought of putting on lingerie makes me hard and I started to ooze precum from my cock just slipping it on. I found a lacy black garter belt and black hose. I put those on and then slipped a black thong on over it all. The thong really wasn’t large enough to cover my now engorged cock, but the thong string felt good running between my butt cheeks. I tend to like the feel of lingerie below the waist. From the waist up I’m still all male. When I got back on the kingsize bed I noted Pete’s now red throbbing erection. Before I knew it Pete and I were fondling and hugging, and pushing out pelvic areas together. Janice just sat back against the headboard and watched us while playing with her clit. Pete and I were obviously ready for this, his hand was traveling all over my body. Kissing didn’t seem to be appropriate with another man, and I think he thought the same thing. That is mouth to mouth kissing, but kissing and fondling of the genitals seemed to be quite all right. We were exploring each others bodies like teenages. I felt his hand move down to my butt and then slide between my cheeks. His finger probed and teased my anal opening.

I was getting so turned on. Luckily I had cleaned my anal area before they arrived, in case Pete and I got to this point. I had some condoms and lubricant in the drawer of the night stand and I clumsily reached over and opened it. Janice saw what I was trying to do, and she reached in and pulled them out. She knew just what to do. She opened a condom package and found Pete’s penis and rolled it on, and put some drops of lubricant down between my cheeks. Pete must have felt it right away because all of the sudden I felt him inserting his lubed finger into my anus. It felt so good and I gasped. Before I knew it I was laying on the bed with my legs spread and Janice was putting some additional drops of lubricant on Pete’s cock. I think she was enjoying this as much as he was. Pete spread my legs apart and kneeled to insert his cock up my ass. He did it slowly. I felt his cock head go in first and then he slowly pushed harder and I felt my sphincter muscle relax as his whole cock entered my ass. It was the first time I had had a cock in my ass, and I couldn’t believe how much better it felt than the butt plug I had been using. It was rigid yet flexible and felt so warm in me.

Pete put my legs up on his shoulders and started to move his cock back and forth in my ass. If it weren’t for my red throbbing cock bouncing back and forth between us one would have thought he was fucking a female, with my stockinged legs on his shoulders. Janice reached down and grabbed my cock and began to stroke it. It certainly didn’t take long for me to cum. I shot cum all over my stomach and her hand. Then suddenly I felt Pete push hard against my butt. His cock pulsed and I felt it throbbing as he came. He and I both relaxed and let our orgasms run their course. I could feel his cock shrink slightly and he pulled it out of my ass slowly, just as he had originally entered it.

Pete said, “Wow, that was the first time for me fucking a guy and I couldn’t believe how tight you felt.“

“I am a virgin, that was my first time too.” I said, “That is why it felt so tight. I’ve only had butt plugs up there before.“

Janice was sitting back against the headboard again and masturbating. Pete and I both watched her as she orgasmed again. It was a lovely site to see her as she went rigid and her face showed the pleasure she was feeling. When she came back down she agreed that that was truly erotic. She didn’t realize how sexy it would be to see her husband fucking another man.

I got up from the bed and went into the bathroom to get some warm damp wash clothes and towels so we could clean ourselves up.

I knew it would be a few minutes before Pete and I were ready for more activity so I asked if they would like some drinks. They readily agreed and I went into the kitchen to get some wine and beer. When I came back, Pete and Janice were kissing like crazy and fondling each other. It was my turn to watch as the two of them performed. Pete was ready again with a stiff cock. Janice did not hesitate to take it into her mouth and suck on him. I watched and just couldn’t contain myself. I had to join in. Pete and Janice were in a sixty nine position with him on top. So I quickly went and got the lubricant and put some on my finger. I got behind Pete and ran my finger between his cheeks. He hesitated for a second when he first felt me but did not try to stop me.

I hoped he had had the foresight to douche his ass as well this evening. I found his small ass hole and slipped my finger in. Pete jerked slightly when I penetrated him but they both kept up the oral stimulation. I could see Janice watching as I began to masturbate Pete’s ass. I felt her reach back and pull on my cock. I knew immediately what she wanted me to do. She wanted to see me fuck her husband in the ass. I couldn’t help but comply. I put on a condom and a few drops of lubricant on my cock head , and I straddled Janice’s face and placed my cock at the entrance to Pete’s ass. I pulled my finger out and slid the head of my cock into it. Pete shivered and I proceeded to push all of my 5“ cock into his ass. I could feel my balls hitting his balls and I knew that Janice was getting a up and close eyeful of this action.

Pete’s ass was so tight and it felt so warm that again it took me but a few strokes to cum. That has always been one of my problems, I have very little staying power. I was thinking that after two orgasms I wouldn’t be quite so quick but I was.

Pete must know what sets Janice off, because she orgasmed once again, and I watched her body shudder as she hesitated sucking on Pete’s cock. After a few seconds she began again running her lips up and down his shaft and he quickly came, spilling his sperm down her throat.We all collapsed back onto the bed and just lay there for a few moments.

We all sat there and sipped on our drinks while we recuperated. We all seemed to be wearing down a bit, so we decided to snuggle and perhaps catch a little shut eye since it was now approaching 1:00 in the morning. We laid down on the bed with Janice between us and smuggled in a mass of bare skin. It didn’t take long for me to dose off.

I woke to the chirping of birds outside the window and the sun shined into the bedroom. As I stirred Pete and then Janice opened their eyes and smiled at the memory of the previous evenings activities. I suggested a shower before breakfast so we all trooped nude into the bathroom and I started the water. Since the shower only had room for a couple of people we decided one would brush teeth and shave, etc. while the other two got into the shower. Pete volunteered to brush his teeth and shave first while Janice and I climbed into the warm shower. We both got wet and then I took the bar of soap and began rubbing it over her body. I lathered her well with the soap and then sat it aside and continued to lather her body with my hand. Oh my, what fun that was. I gently washed her face with my hand, and then ran it down to her neck and shoulders. She rinsed her face while i grabbed the soap again and lathered her back. I again used my hands to scrub her back and buttocks, running my fingers between her cheeks and tentatively probing her anus slightly. She didn’t object so I scrubbed it a little more delving my finger into it to clean her a little and see how she liked the probing. With my other hand soaped up I reached around and massaged her breasts, fondling and then gently pinching her nipples. I eventually moved it down onto her pubic mound, and I slowly delved her pussy with my fingers. Here I was probing her anus with one finger on my right hand and her pussy with another finger on my left hand. I could see her beginning to get aroused as I continued to probe and play. After I had gotten her a little bit stimulated I told her to rinse off and I would finish washing her. She did and when she turned back to me I took the soap and dropped to my knees so I could wash her legs. I soaped up each leg and then set the soap aside and began slowly running my hands up and down her smooth and shapely legs working up a lather. I would deliberately slip up between her legs now and then and slide into her pussy which was now dripping from something other than soap and water. After a few minutes of this I took one foot and told her to hold on while I put her foot onto my leg and rubbed and washed her feet. I managed to do this despite my throbbing erection that kept getting in my way. After I finished with her feet she rinsed off again and then turned back around as I stood and put my arms around her when she did. I lowered my lips to hers and began a slow and deliberate kiss as my hands wondered over her wet and soft body. I massaged her buttocks and her breasts and then moved it between her legs as we continued to kiss and probe each other with our tongues.

All of the sudden we heard Pete yell, “Are you guys going to stay in there all day?”

I pulled away and looked at Janice and smiled.

“I guess I should share you with your husband,” I said.

I then proceeded to open the shower door and step out.

“Your turn,” I said to Pete as we side stepped each other.

I grabbed a towel and started to dry off, as I heard Pete and Janice begin to splish and splash in the shower. I could see them fondling, kissing, and groping each other as I proceeded to shave and brush my teeth again. I had already brushed the sleep out of them before Janice and I stepped into the shower.

I left Pete and Janice to their ministrations, while I went into the kitchen to prepare a little breakfast. I began a pot of coffee and poured juice for all of us and then began cooking a little French toast. In a matter of about a half hour Pete and Janice emerged completely naked and famished. I put all the food on a tray so we could take it out on the back deck and eat. I ran into the bath and got three fresh towels to use for sitting on and got back out to the deck as Pete and Janice arrived with the food.

We sat in the sunshine and chatted and ate breakfast nude while birds sang around us.

“After breakfast I’d like to give you both a massage if that suits you,“ I said. What fun it would be to slowly massage each of their bodies and feel all parts of their bodies. I was getting hard just thinking about it.

Life doesn’t get any better than this. What a fantastic pair I had stumbled onto. And the adventure was just beginning.