If you've read the first in this series, you'll know I am Emma, and ex high-school slut that now commands a very good position with a big legal firm in the heart of then city. I recently met young Liam a chap who works in out IT department at a party dressed as a slutty girl, a real sissy. I wanted to know his story and so now I had the young Liam standing bollock naked in front of me, his slender 4.5 inch dick standing out rock hard, not very proud as it was too small to be proud, but it was definitely dripping pre-cum as I, Emma a very hot sexy 29 year old woman, sat, fully dressed in front of him waiting to hear him tell me about his 'sissy' cuckold life with his beautiful girlfriend Cassie.
The Sissy, Liam Harper
His face was refined, with symmetrical features and full, soft lips that lent him a "pretty boy" appeal, making his look both striking and memorable. His lean body was toned but not overly muscular, highlighting more of an athletic, slender build that suggested agility and balance. He carried himself with an easy confidence, his appearance balanced between softness and strength. His style was casual but polished, fitting his effortless charm and natural beauty. Altogether, his look blended masculine and feminine appeal, giving him an androgynous quality that was captivating and unique, drawing attention wherever he went.
And his rather mean young girlfriend, Cassie Bennett
Her brunette hair fell in natural waves, framing her expressive, hazel eyes that revealed determination and focus. Her 34B bust added balance to her athletic figure, lending femininity to her strong, well-defined upper body. She embodied both softness and strength, a blend of curves and muscle tone that reflected health and vitality. Whether dressed in workout gear or everyday clothes, her posture and the confidence in her movements made her presence noticeable. Her skin, likely with a subtle sun-kissed glow from outdoor activities, completed her look as a true gym enthusiast, living the lifestyle of discipline, energy, and passion for physical well-being.
This is his story:
The first time Cassie dressed me up I didn't even realise I was being dressed as sissy. I thought it was just fancy dress, until I got to the party and realised, I was the only guy there dressed as a girl. We had gone to a friend's party, and it was supposed to be 'Pimps & Tarts'. Of course, Cassie insisted on being my pimp. I didn't realise this was going to become a new lifestyle.
Cassie had dressed in a 'Gangsters' expensive track suit, with the bottoms hanging around her ass. But instead of wearing boxers, she had on a very skimpy little thong which was completely on show above the low hanging tracksuit bottoms, which also showed off half her incredible round booty. Below the jacket she wore a very tight skimpy vest top with no bra. Her beautiful 34B very perky breasts were very much on show, with her nipples making sharp points through the thin material. She also wore several heavy gold chains and a beanie around her gorgeous brunette curls.
For me Cassie had dressed me, against my many protestations, but Cassie always gets her way, especially when she takes my slender dick in her hand. The first thing she did in the afternoon was make me take a long bath, then she came in and we spent an hour shaving and waving all of my body hair. I argued against it, but she insisted on even doing my ass crack. When she finished, she spent another half hour smoothing in body lotion all over. My dick was throbbing. She told me that if I behaved myself dressed exactly as she wanted me to, then she would wank me off before we left for the party.
So, she had got me to squeeze into one of her little pink thongs. I was very surprised how comfortable it was; the little triangle of material cupped my little dick and balls very nicely. The she had bought me a very short white mini skirt, more of a micro-mini as it barely covered my round bubble butt, leaving the lower moons fully on show. The pink thong clearly visible above. It was very girlie. The she had bought me a matching pink to bra, and a see-through white crop top that left my flat stomach on show. To round off the outfit and to show everybody I was her 'tart', she fixed a pink dog-collar around my neck and had a pink leash. She did some very light make-up, mainly eyeliner and thickened up my eye lashes, but added pink lipstick that matched the pink of my skimp underwear. She gave up on getting me to wear heels as she didn't think that I would learn to walk in them in time but bought me a very cheap pair of pink trainers. When I checked in the full length mirror I was horrified to see just how pretty I looked transitioned into this slutty girl.
Once we were both dressed, she took me back into the bathroom. "You've been a very good boy, so, slut, as your pimp I get to wank you off." She stood me in front of the mirror and told me, "She's hot isn't she," pointing to my refection. Pulling my hard dick out from the little pink thong, she started to stroke, "Tell me baby, would you fuck a hot girl like this? Would you bend her over and push your dick into her boi-pussy?" I felt so fucking humiliated and so fucking turned on. I'd never had any gay feelings. Yes, like anybody, I'd always been curious about the other guy's cocks in the showers after football. But that was normal curiosity. We all want to know how we compare to others. I had a very intense orgasm shooting my load into the loo.
My beautiful Cassie ordered us a taxi to take to the party and I went to put my coat on, and I commented that it'll make it look like I'm naked underneath.
Cassie: "Baby, you're not wearing a coat, you're coming to the party as you are."
"I can't walk don out to the taxi dressed like this and then let the taxi driver see me. I'm dressed like a teenaged slut, a middle-aged man's wet dream."
Cassie: "It's fancy dress, babe. People will understand your in fancy dress." Then with a naughty glint in her eye, "Do you think if you give the taxi driver a blowjob we wouldn't have to pay."
I knew she was joking; I thought she was joking.
"I'm not sucking any cock, baby, even if I am dressed like a cock-sucker."
Cassie, still with that slightly naughty glint, "Are you sure, you look like a naughty cocksucker to me," And as we went out of the front door, she gave my ass a very hard slap.
Cassie; "Ooooh! Naughty, I can see the red mark on your cute ass."
"No way! I hope not."
To my horror, when we got outside and the stepped up to the taxi, she reached for the door handle opened the door and indicated for me to step in first, as I did so she gave my other cheek a very hard slap. The driver turned and smiled knowingly at me then turned away when he twigged I was man. I was so embarrassed. When cassie was in beside me, she noticed and said, "Oh baby! Now all your cheeks are bright red," and gave a very naughty laugh. She was really enjoying the power this gave her. Literally the boot was on the other foot.
Cassie leaned into me and whispered, but quite loudly so there was a very good chance the driver would hear, "Move into the middle and open your legs flash him your little pink panties."
I looked at her and vigorously shook my head.
Cassie: "You're such a spoil sport." Then she leaned into me again and whispered so that the driver definitely couldn't hear, "if you don't do as I say when we get to the party, I'll leave you outside and you know where it is? It's a rough neighbourhood, when I eventually come back to find you, we'll see how many of the local thugs have raped your ass and mouth."
Humiliatingly I slid into the middle of the seat and opened my legs. The skirt was so short that with my legs open it was like it was just a little belt. My thong barely covered little dick was fully on show. I met the eyes of the driver in the mirror. I knew with the angle of the mirror he wouldn't be able to see anything below my chest. We looked at each other for a few seconds then he reached up and angled the mirror down so he could see my little pink thong.
Cassie giggled at what was happening, "Baby, having the driver looking at your little pink panties is making your little dick hard."
To my utter shame it was. I went to close my legs, but Cassie grabbed my nearest thigh and said loudly, "Keep your legs open for the nice driver or I'll make you show him your little dick and wank for him the rest of the way."
For the rest of the journey, I had to sit there with my legs spread and my hard little dick pushing out against the tiny bit of pink panty material covering it.
The party was in a house in a street of terraced houses. The taxi pulled up outside and the driver passed my girlfriend his card saying if she needed him to pick us up later tonight he'd happily give a discount.
Thankfully it was a very short walk from the car to the front door. But as we got out three young men were walking up the street and seeing what they thought were two very hot, sexily dressed young women getting out the car, they called out and wolf-whistle at us. At that point I was very pleased I'd done as I was told in the car and my girlfriend took me, leash in hand, straight into the party.
At the party it didn't take me too long to realise that I was the only guy dressed as a girl. My girlfriend led me around, she was being her usual fun, flirty self and dressed as sexily as she was, she was getting a lot of attention. This evening, with me dressed as a slutty girl the guys were not put off by my presence in making quite obvious passes at her and she was lapping it up as if I wasn't even there.
As we moved round the party, we'd picked up a couple of drinks and gone and had a chat to the hosts, Cassie's boss at her part time job and the man's wife. They complimented us on our outfits and remarked to Cassie what a brilliant idea to reverse the genre and have her as the pimp and me as a tart. The woman then turned to me and spoke to Cassie; "My God, Cassie, you've done such a good job dressing him up, he really looks the part." Then to me, "You're going to have to be careful you might get the kind of attention you don't want, unless darling you really do?" And she gave me a big wink.
I thought at that moment, "Fuck, she's suggesting I might want to get it on with another man. Ewww, no!"
We then went around the party chatting to different people complimenting on others as they did with us on their cool outfits. But these were mainly Cassie's friends, and I often was just stood behind her like a spare wheel. Any of the single guys were not shy at chatting Cassie up, since I was dressed as a tart, it was as if I was no longer important and could be ignored like I was no longer her boyfriend. What man is going to take a boyfriend seriously who is dressed in a pink thong and bra, both totally visible.
We had been at the party for about an hour and a half when there was one particular guy that hit on cassie, he was probably in his early forties, remember my girlfriend is just 19 years old. This guy was dressed up as Captain America and, fuck, did he have the body for it. He must have been well over six foot, very broad and with rippling muscles all through his skintight suit. What was also obvious in his tight leggings was his package. I remember wondering at the time if this was real or if he had stuffed some socks down there. But to be fair, with his size, if he didn't have a big dick then on his large muscular body a small dick like mine would've looked ridiculous.
It was as Cassie was lapping up all the attention from Captain America when what I feared might happen, happened. I was stood a full leash length back from Cassie, so I wasn't cock-blocking her, and I felt a big strong hand grab a very firm hold of my right ass cheek. The problem was, with the very short skirt, his fingers were flesh-on-flesh gripping the lower moon of the cheek.
The stranger leaned in and whispered in my ear; "What a cute little thing you are, showing so much flesh."
