Transsexual

Anal Pleasure – Chapter 1

/ Categories: Anal, Pegging, Toys, Transsexual, True Story / Anal, Pegging, Toys, Transsexual, True Story / By

My journey into the delights of anal sex began a decade ago. I fantasised about my then wife and I having a threesome with another woman. My wife just thought I wanted to fuck someone else. She couldn’t understand I wanted to see HER with another woman. I even bought a strapon dildo for her to use but she wasn’t interested at all. The toy got filed in a drawer. Sometime later we were making out on the bed when she said she had to go to the toilet. Several minutes later she came back naked wearing the strap-on. “Strip” she demanded. Then I got in the doggy position and had my first anal experience. I am not embarrassed to say I enjoyed it. She did it once more. I loved being pegged. She was …

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Southern Hospitality Ch.03

/ Categories: Anal, Blowjob, Consensual Sex, Cum Swallowing, Fiction, Older Female / Males, Oral Sex, Romance, Transgendered, Transsexual, Written by women / Anal, Blowjob, Consensual Sex, Cum Swallowing, Fiction, Older Female / Males, Oral Sex, Romance, Transgendered, Transsexual, Written by women / By

Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some blue jeans, combined with a pair of trainers that he had at least taken the time to clean. But.. He bit his lip in consternation. It just didn’t feel right. He wanted to be as dressed up as he could possibly be, he wanted to look like a prince for her, it was the least she deserved after all for all that she was doing to teach him about himself. He let out a delicate little sigh and shook his head, he could make himself look …

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My first time with a tranny

/ Categories: Bi-sexual, Black, Blowjob, Cum Swallowing, First Time, Interracial, Oral Sex, Transsexual, True Story / Bi-sexual, Black, Blowjob, Cum Swallowing, First Time, Interracial, Oral Sex, Transsexual, True Story / By

My first time with a tranny It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn’t make it. Because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited. Within minutes, I received over a dozen new messages. But none of them really appealed to me. Then after a few hours of receiving numerous messages, from both women and some men. I finally got a hit. She was an older white tranny who loved BBC. Her message said: “I’d love for you to fuck me with your big black cock. I’ll be your little white slut, Daddy.” Then she attached a …

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Surprise Second Time with Sensuous Savannah

/ Categories: Anal, Consensual Sex, Cum Swallowing, Interracial, Transgendered, Transsexual, True Story / Anal, Consensual Sex, Cum Swallowing, Interracial, Transgendered, Transsexual, True Story / By

I had all but given up on ever seeing Savannah again and had been seeing a girl but one day, out of the blue, I got an email from Savannah. I was excited as I started to read it, thinking about her and again wanting to be with her. The email started out simple but then she went in to trying to explain why she hadn’t contacted me earlier. She said that she thought I was mad at her for not being safe when she took off the condom and putting her cock back in me. At the time it did worry me but I got over it realizing it was okay. She then suggested that I should come by some time if I was still interested telling me she’d be working the next weekend. …

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Anal Pleasures – Chapter 2

/ Categories: Anal, Asian, Bondage and restriction, Pegging, Threesome, Transsexual, True Story / Anal, Asian, Bondage and restriction, Pegging, Threesome, Transsexual, True Story / By

After my initiation into anal sex I wanted more. I was seeing on old friend (female) and enjoying her. Of course I didn’t mention my new friends to her. I had booked “P” again, this time with her friend “M”. “P” had told me to always book for the next day so she wouldn’t masturbate and be ready for me. She and “M” arrived, this time early. I don’t know if they were keen but I sure was. “P” had found a way around hotel security. I guess she was well versed. I opened the door in shorts and a T-shirt. “P” introduced me to “M” and we sat down and had a drink. “M” went and had a shower while “P” explained all the nasty things they were going to do to me. I …

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Sugar Momma

/ Categories: Bi-sexual, Consensual Sex, Erotica, Fiction, Gothic, Mature, Plumper, Romance, Teen, Transgendered, Transsexual, Written by women / Bi-sexual, Consensual Sex, Erotica, Fiction, Gothic, Mature, Plumper, Romance, Teen, Transgendered, Transsexual, Written by women / By

Julia sat, a little pit of anxiety settling in her as she waited on her sofa, looking at her book but not really reading it, too far gone in her own thoughts to take in in the words written on the page. She glanced instead to her side, out the window. Past her own reflection the view it offered was to most, simply breathtaking, but it, as with most things for her, had steadily lost its charm over time. She owned the prestigious penthouse suite of a luxurious high-rise and the view at night, out over the smaller blocks and bustling streets below was nothing short of stunning, watching the lights move, the tiny shuffling ant-like figures of people as they went about their lives, it made her feel as rich as, well, she was. …

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She’s got an Experienced Eye

/ Categories: Anal, Boy, Cheating, Cum Swallowing, Domination/submission, Interracial, Latina, Transsexual, True Story / Anal, Boy, Cheating, Cum Swallowing, Domination/submission, Interracial, Latina, Transsexual, True Story / By

My girlfriend and I just recently celebrated one year together, and things have been going very well between us. Despite only just turning 18 and approaching the end of high school together, we really felt like we were figuring out love and sex beyond our years. I agreed every time during these conversations, but a part of me knew something within me was changing. I didn’t want to break up, not at all- this change was much more subtle. Recently, I have been spending almost every single night that I am away from my girlfriend dressing up in her clothes and fucking myself with a dildo I bought without her knowing, all on camera for older men I met online. It started as an innocent and casual interest in submissiveness, as well as finding myself …

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The Landlord’s Pet_(1)

/ Categories: Anal, BDSM, Bondage and restriction, Coercion, Cum Swallowing, Discipline, Domination/submission, Erotica, Female Domination, First Time, Hardcore, Male / Females, Non-consensual sex, Older Female / Males, Oral Sex, Reluctance, Science-Fiction, Spanking, Teen Male / Female, Threesome, Transgendered, Transsexual / Anal, BDSM, Bondage and restriction, Coercion, Cum Swallowing, Discipline, Domination/submission, Erotica, Female Domination, First Time, Hardcore, Male / Females, Non-consensual sex, Older Female / Males, Oral Sex, Reluctance, Science-Fiction, Spanking, Teen Male / Female, Threesome, Transgendered, Transsexual / By

Bound, naked and being spitroasted by two cocks is not how I thought I would lose my virginity. I know what you’re thinking, I’m the idiot that got myself into this… Well.. Before you draw any conclusions, let me tell my side of the story first. I also need to state for the record that I am completely 100% straight. Being rammed by two cocks wasn’t on my bucket list, let alone something I would ever fantasize about. You see, this all started when my drunk of a dad took a job as a maintenance repairman for a luxurious apartment complex in New York a month ago. The job did come with perks. We got to live in the smallest available apartment. When I say small, I mean small. I’ve seen bedrooms bigger than our …

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Latex School Girl

/ Categories: Anal, Fiction, Latex fetish, Threesome, Transsexual / Anal, Fiction, Latex fetish, Threesome, Transsexual / By

Not many people knew about my crossdressing. My mind would fill with worries about what everyone would think. I did tell two of my friends, David and Nick. They were experimenting with bisexuality and very open minded. Somehow I knew they would be more understanding, and they were. The three of us lived in a small house for the price of an apartment. It seemed to be a much better choice. In apartments, everyone can hear every little word you say and everything you do. We were all discovering new sexual things and we didn’t want the whole world to hear us. Though they knew, I found myself dressing up when they weren’t home. I guess I wasn’t comfortable yet. I’d been dressing for a little over two years and everyone who had seen my …

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Lost Time

/ Categories: Blowjob, Consensual Sex, Cum Swallowing, Fiction, Gothic, Incest, Oral Sex, Teen, Transgendered, Transsexual, Written by women / Blowjob, Consensual Sex, Cum Swallowing, Fiction, Gothic, Incest, Oral Sex, Teen, Transgendered, Transsexual, Written by women / By

Louise hummed a light airy tune to mask her mounting anxieties as she went about making the bed in the upstairs guest room, her hands moving with a practised grace as she laid out linen and straightened edges, fluffing pillows and generally just wasting time, allowing her mind to wander as she worked. Today was the day, she knew. The day her daughter, Willow, would be making her first visit back after leaving for college, the first time she’d have seen her in over a year. They had talked plenty and texted more besides during her time away, but given their unique relationship, her daughter’s absence had left a void in Louise’s life that she had struggled to fill with a long list of short lived romances and one night stands. In her youth Louise …

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Caught Stealing Thongs_(1)

/ Categories: Asian, Fiction, Interracial, Spanking, Teen, Transsexual, Transvestite / Asian, Fiction, Interracial, Spanking, Teen, Transsexual, Transvestite / By

It was so humiliating. A store security guard caught me walking out of the department store with a pretty, expensive French bra, garter belt, panties and stockings set. I was ushered into the office of the store’s chief of security. I was scared. I was a teenager. It was the first time I had ever been in trouble. But I couldn’t help myself. I’m pretty and I like to wear pretty things. I couldn’t afford the lingerie, but I didn’t need to steal it either. I don’t know what possessed me to do it. Perhaps it has something to do with my secretive nature. I have so many secrets. My whole wardrobe, actually, is a secret that I keep hidden until I find an occasion for dressing up. Likewise, my make-up, my perfume, heels,the falsies …

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TWO MALE GIGOLOS FOR TRANS JULIETTE

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Consensual Sex, Cosplay, Cuckold, Cum Swallowing, Exhibitionism, Female exhibitionist, Gay, Group Sex, Hardcore, Male/Female, Oral Sex, Threesome, Transsexual, True Story, Voyeurism / Ass to mouth, Bi-sexual, Blowjob, Consensual Sex, Cosplay, Cuckold, Cum Swallowing, Exhibitionism, Female exhibitionist, Gay, Group Sex, Hardcore, Male/Female, Oral Sex, Threesome, Transsexual, True Story, Voyeurism / By

I am Damian, a twenty-six year old bisexual male escort or as some prefer a gigolo, though in recent times I much prefer older women. My preferences became much more focused after a recent assignment with a woman twenty-years older than me. Today’s assignment promises to be very exciting, with just one woman for the two of us to pleasure while another woman watches. When we arrive Juliette’s secretary, Mary, greets us and leads us into another room to meet Juliette. Mary is very plain and unfeminine, though the thought of her watching us sexually pleasure her boss is already a bonus turn on. Juliette is an absolute knockout, smooth ebony skin, stunning exotic features (we learnt later she was part Asian, part European), a beautifully groomed, very feminine, tall willowy blond, with shoulder length …

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Life on the Ranch pt 1

/ Categories: Anal, BDSM, Bondage and restriction, Discipline, Domination/submission, Fantasy, Female Domination, Hardcore, Humiliation, Job/Place-of-work, Non-consensual sex, Rape, Transgendered, Transsexual, Transvestite, Violence / Anal, BDSM, Bondage and restriction, Discipline, Domination/submission, Fantasy, Female Domination, Hardcore, Humiliation, Job/Place-of-work, Non-consensual sex, Rape, Transgendered, Transsexual, Transvestite, Violence / By

I can’t believe those jerks threw cattle dung at me. No good, dirty rotten, a-holes. They got that shit all over me. That’s not even the worse part… Well, that’s up for debate. But to top it off we’re out of hot water! I had to wash the bull shit off with freezing cold water. I hope to god Steph gets back soon. I wish I could tell her what those jerks did, but I know we’re in desperate need of help. I don’t know how much longer I can take their crap. Always calling me all sorts of derogatory, crude, insults. The owner’s daughter or princess are their favorites, knowing full well that I’m a boy. Pillow bitter or mattress muncher are some other terms I’ve heard them call me, especially Bruce! Honestly I …

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Jena and Lisi Ch. 3

/ Categories: Blowjob, Fan fiction, Group Sex, Science-Fiction, Threesome, Transsexual / Blowjob, Fan fiction, Group Sex, Science-Fiction, Threesome, Transsexual / By

The mysterious black robed figure waved his fingers through the air. The girls could not resist his power and knelt on the floor before him, their arms behind their backs, their heads up in the air, and their bodies presented to him. A figure stepped out of the shadow of the black clad warrior. She wore armor similar in style to the ground troopers, yet the color was of the shiny silver Nubian style spacecraft that occasionally graced the skies of their home-world. Cum still dribbling from their lips, the two girls were roughly pulled to their feet by the squad of troopers that surrounded them. They quickly slapped stun cuffs on them and if that wasn’t enough, for some strange reason neither of them could touch the Force anymore! Kylo and the silver masked …

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JULIE’S FOUR WAY.

/ Categories: Bi-sexual, Blowjob, Cheating, Consensual Sex, Cuckold, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Lesbian, Oral Sex, Threesome, Transsexual, True Story / Bi-sexual, Blowjob, Cheating, Consensual Sex, Cuckold, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Lesbian, Oral Sex, Threesome, Transsexual, True Story / By

“Tell me more, I am intrigued.” Minutes later I am more than intrigued and ask Ros to make it happen after she told me, “Let’s stretch the boundaries, a foursome, Carla for your man and me for you.” I had recently watched Ros blowing my man while I had two men pleasuring me, though she had never even laid a finger on me, so the thought of her providing sexual pleasure for me has great appeal. And perhaps me pleasuring her in return. My man and I have never seen her naked, something I am looking forward to. I am Julie, I am blessed with a high sex drive. My man Charles and I are in our early forties, we are both bisexual and we enjoy an open relationship with an extra man or woman …

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