Sissy Giving Head free porn video

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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:

Hi,
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 c******n. 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.

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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.

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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.

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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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  • 17
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

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