Confessions Of A Cross-dresser June 29, 1982 free porn video

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It is 8:35 on a warm summer morning. I hear the front door close and already the excitement is building. I hear the car start and then pull out of the drive way. I run to the front of the house and watch my mother pull up the hill and off to work. My sister left for work 5 minutes ago and Dad is gone until 2PM.

I turn and walk up the green carpeted stairs. With each step I feel my heart pounding harder and harder. As I reach the top of the stairs I take one last look out the window to make sure mom has driven out of sight. I turn left and open the door to her room. Instantly the smell of chanel permeates the air. I make my way into her room and turn to the large wooden dresser that takes up the entire wall.

The titillation of what is about to happen makes my little cock start to pulse. As I look down I slowly pull down my fruit of the loom briefs which have a tiny bulge from my half erect penis. I kneel down and fall to my right side and slowly reach for the middle center drawer of the dresser. The anticipation is building as I can't wait for what is inside.


The smooth sound of the wood as I pull the drawer open heightens the tension inside me. There it is, my favorite thing in the small world I know. An old JC Penny bag with a string closure. I remove it and gently open it. My mother's lingerie lays inside. As I reach in I am so excited I can feel my heart beating through my chest. What shall I wear today? I separate the lingerie into possible outfits, laying my favorites to the side. Before I can make my choice, I open the top center drawer of the dresser and put on my favorite white slip that she owns. The feeling on my skin is pure ecstasy. I feel it gently kiss my penis and can feel the soft fibers slipping in the crack of my bottom. I pull the slip up to under my arms which I pretend is a sundress that barely covers my penis and comes to rest at the top of my thighs.

At age 4 I used to sneak into my mothers room and put on her panty hose and high heel shoes. The first time she caught me, so laughed and took a picture. She told me never to do it again. The next day she came into my room and I was under my bed. She made me come out and there I was again in her panty hose and high heels. That feeling has never left me. The excitement of wearing ladies undergarments throughout my life has always brought me back. This went on for a week or 2 and freaked my mom out so much she ending up talking to a shrink about it. She bought me girls panties and took them in to fit me but those crappy cotton things just wouldn't do it.

Back to her room, I have decided. I have always had a love affair with white lingerie. I pull out a pair of her white stockings, her white garter belt and a pair of her white panties. I pack everything that I am not wearing back, just in case someone come home I can get away quicker. Taking the white garter belt which is made of soft see though lace I clasp it as tight as it will go and pull it up my smooth hairless legs, then over my hairless scrotum. I pull it over my penis as I continue up to my belly button. They tickle as the straps brush against my thighs and over my buttocks. As I sit on the floor I lay the stockings out and grab the top of them. I carefully slip my right foot into the nylon making sure to stay straight with the seem and toe and instantly fell the rush. As I slide further and further in, the sensation and silkiness gets me more and more aroused as it inches up my thigh. It comes to rest right at the point where my leg meets the bottom of my bottom. I reach down and clasp the stocking to the garter belt behind my thigh. I repeat on the front. Now I do the same with my left leg. I stand up and put her satin bikini style panties on as I am now fully erect with the soft touch of them on my penis.

I then head to the closet. I walk in and find a pair of silver high heels which are open toed and have fake diamonds in them which run around the toe hold. I sit down on the floor and let the slip hang off me and down my body. I slide my feet into the heels and I reach down and put the strap through the 1/4" buckle and tighten them to the very last hole, which still barely holds my ankle in place and the shoe on. As I exit the closet I walk into the bathroom. I walk back and forth on the tile floor to hear the clip clop of her heels on the floor. I spin and twirl as I watch the slip, my sundress flow back and forth across my midriff and then repeatedly come to a rest on my bare skin. I sit on her bench with legs closed and move my hands from my breasts down across my stomach. As I reach my crotch, I ever so slowly open my legs to let my imaginary mans hands touch my genitalia. I softly run his hands over my whole body to make sure every piece of skin is tantalized by the soft silk. Then, I walk as seductively as I can back into the bedroom to her full length mirror and look myself up and down.

I then erotically pull down the slip, making sure I press it against my body and slide it down my back. I make little circles with it as I cautiously move it over my derriere to make it feel like the a man behind me who loves to touch every area of my body. I then bend over like you see pin up models do and slide the slip off, letting it rest on the floor as I step out of it. I then look at myself in her mirror as by this point I am so aroused I am ready to burst. I turn around and look at myself over my shoulder to make sure the lines on my stockings are straight and her panties and smooth and tight across my bottom.

Now I go back to the middle drawer and in the back corner, under her sweatshirts I take out a little brown box which is about 2 1/2" wide and about 8" long. It has a gold label on it which says "Mr. Squirmy." I take the top off and it is a flesh colored dildo which feels almost real. It is a little soft and has a little metal rod coming out of the bottom. I hold the bottom of the penis tightly and turn the rod and Mr. Squirmy starts to squirm. I take it over to her bed and kneel down like I am saying my bedtime prayers. I get on my knees and with her beautiful cock on the bed I imagine a man would be sitting there, waiting for me to start pleasuring him. I lean over and begin kissing this beautiful penis. I kiss and lick up and down the shaft, making sure I get every inch of the vein which runs down the underside. I then put my tiny mouth around it and start just sucking the tip of it. moving farther and farther down with each entry.

As I continue to lick and suck I reach down and start rubbing my little erect penis cautiously so I do not ejaculate. I bring my hand back up and work up a good load of saliva so I can get Mr. Squirmy drenched and holding him firmly I give him a hand job. As I am rubbing his shaft, I make sure I continue to lick the top of his cock. I am so excited feeling this cock in my hand and mouth, my penis rubbing my satin panties, the stockings on my legs and the pressure of the shoes on the bridge of my feet I am ready to cum to completion.

I turn to my mom's night stand and take the cap off of the jar of Vaseline and I pull out her conair massager. I unwound the cord from the handle and removed her attachment and put on something that looked like a cup. I slide it through the slide of the panties and forced my erect penis down into the cup. I plug it in and turn it on high, which gives a fast but slight vibration to my penis. As I slowly move toward a feeling of euphoria, I continue giving fellatio to the cock in front of me which seems to get bigger with each thrust into my mouth. I dip the tip of my finger into the Vaseline just enough to coat the tip, I reach down and slide the back of the panties over and put the slightly cold ointment on my anus. I pull the underwear back into place and I run my fingers between my legs and with my middle finger, I start rubbing my anus through the satin. As I rotate and shove the sweet tasting cock in my mouth, I push farther and farther into my ass with my finger, finally penetrating myself. I keep sucking and fucking for what seems like an eternity. I put down Mr. Squirmy and turn the conair down to low, which gives a deep hard vibration to my rock hard cock. I pick up Mr. Squirmy again and start sucking as hard and as fast as I can, making sure to keep it wet with my spit so it is dripping off my hand and onto her bedspread. The sounds of slurping and popping from it going in and out of my mouth are driving me wild! I continue to shove my finger deeper and deeper into my ass which is so tight, it starts to hurt a bit. I keep going as I am about to come to climax.

Now that I have reached the point of no return, I start clinching and tightening my penis to make sure when I cum, I have the hardest orgasm possible. I keep sucking wanting him to cum in my mouth as I suck him through orgasm. As I am about to cum, I shove my finger in as far as it can possibly go, my back goes straight, my penis presses as hard as it can against the cup and I shove the cock in and out of my mouth as fast as I can. I AM CUMMING as my body starts convulsing. My ass is clinched so tight, I couldn't remove my finger with a pair of pliers. I start pulling down with the tip of my finger milking out every last bit of cum as I writhe with each pulse of my penis. I try to scream but Mr. Squirmy only allows muffled growns. As I finish my orgasm, I slide the finger out of my ass and carefully reach down the front of my panties. I pull the conair out carefully so I don't spill a drop. I take the cock out of my mouth and put it upside down on top of the cup. I turn it over and take off the cup, instantaneously I start sucking it again feeling the warm cum in my mouth. I swallow everything and keep putting it in my mouth to get everything off of every crevasse around the head and vein on the shaft. Like when I started, I lick and kiss it like I was worshiping it.

Before I do the usual clean up I put my sundress back on and I still wear the lingerie and heels. I seem to walk a little more like a girl after sucking a good cock and being fucked in the ass. As I walk back and forth from the bathroom, my ass cheeks slide against each other from the Vaseline all over my anus. I put Mr. Squirmy back in his box and then go to the closet. I unbuckle my high heels and kick them into the corner; I go into the bathroom and wash mom's panties and use her blow dryer to hide the stains I made. I put them on one last time to walk back into the bedroom. I look in the mirror one last time just like a woman who is about to go out for the night. I open the drawer and take out the bag. I remove her panties and I unclasp her stockings. I take the stockings off one at a time making sure to make the sensation last as long as possible.

With everything put away I make it back downstairs awaiting my next chance to wear her lingerie again. Maybe tomorrow. Well it is only 10:00. No one will be home until around 2!

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June arrived home shortly before her parents and Autumn were due. She ran upstairs and showered, shaved her legs and pussy, dried and brushed her hair, put on some make-up, and went downstairs. Only minutes later, her parents and Autumn walked through the door. “My, aren’t we all prettied up tonight,” Autumn said when she saw June sitting at the table. “I take it you’re not dining with us tonight, are you?” “Hopefully, no,” June responded. “I’m waiting for Roger to get home and call me....

3 years ago
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June and AliceChapter 7 Sayonara Marilyn

Monday morning came quickly, too quickly as far as June was concerned. Roger would be leaving this morning to present a proposal to a firm in Buffalo. Yesterday, June had convinced him to change his plans from coming home this evening to early tomorrow morning. Ordinarily, she would have liked him to return home on the same day, but not this day. This day would end with her final party at Alice’s, and keeping Roger as far away as possible was necessary lest he discovers the activities planned...

3 years ago
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Abduction and rape of June

ABDUCTION AND RAPE OF JUNE. June's only daughter Megan, while walking to school had been abducted and was probably by now being raped and tortured. It brought back memories of when June was a little girl of 12 years of age and she had also been abducted, raped and tortured. June was thinking about that awful day. How she had been lured into a van by a "nice man and his wife". She had then been tied up and driven to a quiet place and there she had been stripped naked, raped and tortured. Before...

4 years ago
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June Autumn and RogerChapter 37 Lights Camera Action

June awoke to the sound of her alarm clock and looked at the clock through blurry eyes. It was 5:30. She now regretted that she had set the alarm for such an early time. She went to bed early last night, hoping to get a fresh start the next morning. It wasn’t because she was eager to get to Alice’s for the movie shoot. No, it was because she wanted to think about her role in it and how well she would perform. She had a restless night thinking about how Alice might punish her if she made...

3 years ago
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June Autumn and RogerChapter 38 Junersquos First Week On the Job

June awoke to the sound of her alarm clock. “It’s Monday. My first day on the new job,” she said to herself. Roger got home too late for her to see him on Friday night. She spent almost all day Saturday with him, however. They made love, talked a lot about a lot of things, made love, went to lunch, came back to his apartment, made love, watched TV, showered together, went to dinner, came back to his apartment, and made love. She hadn’t seen him in over a week, but they certainly made up for...

3 years ago
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June Gets Blackmailed

By Docker5000 Introductory Jason sneaks out of school and meets his older friend. The two lads discover Jason’s mother having sex with two men in her living room. Chapter 1 Jason Clark was extremely bored as he sat in class as his teacher went on about something. Jason was completely ignoring him. Jason just continued to look out of the classroom window. His regular English teacher was off sick and the substitute teacher that was standing in for her was completely...

4 years ago
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June The Sexiest Manipuri Party Girl

Hi friends, am back with the continuation of the story of June, the sexy Manipuri babe. June was 19, a Manipuri (chinki) girl but not the usual trashy cheap looking one. She was elegant in poise and had the look you see among tall Asian models. Her height was 5 7″,a lot more than usual Manipuri girls. She had perky breasts, shapely legs, and a tight curvaceous ass with a figure of 34B-26-36, a body guys dreamed of while they jerked off into the night calling her name over and over again. Her...

2 years ago
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June and AliceChapter 3 Alice Throws another Party

June pulled into Roger’s apartment complex and parked next to Roger’s car. She got out of the car and glanced over towards Alice’s apartment. June couldn’t remember if Alice told her not to call her this morning as well as tomorrow morning. Playing it safe, she quickly took off her dress and panties and picked up the telephone and dialed Alice’s number. “Hello,” Alice answered. “Alice, it’s June. I wasn’t sure if I had to call you this morning or not, so I thought I had better call to be...

4 years ago
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June and AliceChapter 10 Loving Maddy

June arrived at work early on Tuesday morning and found the apartment dark and empty. She went into the kitchen, made herself a cup of coffee, and sat down at her desk. As June sipped her coffee, she remembered that Maddy wanted her to call today. June looked at the clock and saw that it was only eight o’clock. June decided to wait to call until nine o’clock or later when she was sure that Rick was at work. She didn’t know if Maddy only wanted to chat or talk about June sexually dominating...

3 years ago
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June and AliceChapter 8 Rick Maddy

After a somewhat restless night of worrying about her future with Rick and Maddy, June awoke and looked over at the nightstand clock. It read 7:40, and June threw off the covers and jumped out of bed. Of all the days that she was late getting up in the morning, this had to be the worse day for it to happen. Roger could walk through the door at any moment if he decided to leave Buffalo very early in the morning. She ran naked into the kitchen, put on a pot of coffee, and jumped into the...

4 years ago
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JUNE AND THE TRUCK STOP BY DOCKER5000

PART 2 BY DOCKER5000 Introductory It had been just over a month and June is still haunted by what the two drifters did to her. She is now desperate to feel that way again. And a over-heard conversation hopefully can give her that chance to feel alive once more. It was nearly a month after June’s experience with the too drifters and she still cannot get them out of her head. Her husband and son still do not know anything about her sexual adventures with the two men. As far as they both...

4 years ago
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June Autumn and RogerChapter 33 The Shopping Fun

June awoke on Monday morning and sat on her bed, wondering what she was going to do all day. She looked over at Autumn’s bed and saw that it was empty. She got dressed, ran a brush through her hair, washed her face, and staggered downstairs to the kitchen. The house was eerily quiet. A note from Autumn laid on the table where June usually sat, explaining that she was at the store helping mom and dad. June made herself a bowl of cereal and ate her breakfast. She looked at the clock and saw it...

3 years ago
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June Autumn and RogerChapter 18 Alice Joanrsquos ldquoPartyrdquo

The week flew by without June having to submit to any of Autumn’s humiliations. Of course, she still had to crawl naked to her sister’s bed each night and thank her each night. Today, however, was different. Today was Thursday. Today was the day she would be going to the doctor’s for an examination and, hopefully, get the prescription for birth control pills. Today was the day she thought would never come. Today was also the day that she was going to be punished by Autumn. It was the only...

2 years ago
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June and AliceChapter 2 Another Party Is Planned

June awoke early Friday morning after spending a restless night thinking about the events of yesterday’s party at Alice’s. What bothered her most was Alice saying that she owned her and that she would have to do whatever Alice wanted her to do. Then she remembered that she had to write down all the things that would humiliate her. At first, she thought that would be easy, but now she realized that she would be giving Alice even more ideas. As if Alice needed any more ideas. June looked over...

4 years ago
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Peter June and the Whatevers

There are times that you know, right from the start, that something's going on, and it ain't quite kosher! Like I did that night when I awoke at some unearthly hour and instantly became aware that standing beside the foot of my bed was an apparition ... To-whit, one patently beautiful and very naked female! In fact I could only just make out her form; but I could see enough to recognise that she was completely naked, and that her figure went in and out in all the right...

3 years ago
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June Autumn and RogerChapter 25 The Dog Show

June awoke early on Saturday and looked over to her sister’s bed to find it empty. She sat up and recalled the events of last night and how earnestly Autumn had begged her to let her lick her entire body and how her big sister had used her tongue so effectively in all of her orifices. When June was satisfied with Autumn’s performance, she sent her to her bed with orders not to masturbate. June then recalled her earlier talk with Roger and wondered how, and if, she would end this part of her...

2 years ago
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June This Could Be The Beginning Of A Beautiful Friendship Part 1

My name is Matthew and this is my story. After the death of my wife due to a lengthy battle with ovarian cancer, I began to search for some female companionship. Bars, church, and friends and family were not the answer. Instead, I joined a senior outdoor group. That is where I met June. June was approaching sixty, but looked ten years younger. She was five foot four with salt and pepper hair, nice breasts and a tight ass. We seemed to instantly hit it off and became close friends. The two of us...

MILF
3 years ago
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June Autumn and RogerChapter 15 June The Patient

Sunday night June thanked Autumn profusely by not only licking her pussy but her ass and tits as well. The rest of the week went by without incident. Oh, she did have to crawl to Autumn’s spread legs and thank her but she wasn’t ordered to satisfy her sister’s sexual needs. Not that she wasn’t grateful, but, for some reason, she found herself drawn to Autumn’s pussy and had an almost irresistible urge to kiss it. She began to wonder if she was obsessed with performing lesbian sex. When her...

1 year ago
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An Ordinary Adult Sex LifeChapter 2 June

-- FRIDAY, JUNE 29, 2007 -- 8:47 AM The San Francisco Jonathan Kwong Enterprises office wasn’t anything like the one in New York. There were no JKE logos on the entry doors or signs on the outside of the building. Instead of occupying the top three floors of a massive skyscraper with its own helipad, we had only the twelfth-floor in a smaller, nondescript building. All the big movers and shakers in the company were in Manhattan, and sometimes it felt like the only reason we even had a San...

4 years ago
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Confessions of a Photographer Part Three

Part One https://xhamster.com/stories/confessions-of-a-photographer-55770Part Two https://xhamster.com/stories/confessions-of-a-photographer-part-2-56377(Please note the people mentioned in these stories are fictional and bare no relationship to people either alive or dead. These stories contain explicit sexual descriptions and are aimed at the over 18’s)Most days were the same though my learning curve was fast and within a few months I was able to set up the studios for the different types of...

4 years ago
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CONFESSIONS PT 9

CONFESSIONS PART 9======Yes, I do sometimes wear panties in public. I remember the first time. I wore a pair to school one day obviously I picked a day when we didn’t have gym class! I remember the thrill of it and the fear of being caught. I think I must have had a hard on all day! Now, to be honest, I wear them most of the time because I still love the softness and lightness of the material. Just plain black simple cotton ones - I must have a couple of dozen pairs. Sometime I do wear guy...

4 years ago
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June Autumn and RogerChapter 31 The Patient Redeux

Saturday evening, after dinner, June decided to ask her parents for permission to stay overnight on Friday. “Mom, Dad,” she began. “One of my girlfriends asked me to come to a sleep-over this Friday. No boys will be there. Only a few girls are getting together for a little fun before I graduate. Can I go?” June’s father looked at her mother, who nodded in agreement. “Yes, you can go. Behave yourself and try to be home before we leave for the store Saturday.” Her father replied. June...

2 years ago
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June Takes Her Oral Exams

After June visited Toyland, it was now time for the oral lessons in her hot sex education. I knew the oral section would not be difficult for June. She was a natural. We waited about a week before the oral lessons began. That gap in time was an extremely difficult for June. She was like an insect emerging from a cocoon. She wanted and needed sexual relief. We talked about our agenda for the main event. I told June it would be a three part lesson. For June, her part would be to give a tit fuck,...

Oral Sex

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