Author: SuitsWithStockings

Dressing for [M]y flat[m]ate to help him through lockdown

Hi all

Long time no posting.

So, Covid sucks, right? Well so do I. Since the U.K. lockdown started last year I’ve had to do my best to cope with basically being stuck in my flat all the time. My flat mate has a suppressed immune system so we’ve had to be super careful to make sure he doesn’t get infected.

Even when things were relaxed slightly last summer we didn’t go out much, the risk was too great to him if one of us caught it.

We got into a rhythm of living effectively through a pandemic. I started to go on cams to make a little extra money and give myself an excuse to dress as a girl and be a slut again. My flat mate, Gary (not his real name) knows that I’m bi, knows I’m a cross dresser and he’s cool with it. He’s seen me plenty of times as a fishy girl and he doesn’t bat an eyelid.

Around September last year his girlfriend broke up with him. They’d been having problems before the pandemic but after 6 months of not seeing each other she threw in the towel. He was crushed. He was really upset and fell into a bit of a depression. Read more »

The time I [m] was used by my boyfriend [m] and 4 other [m]en

Just before Rick and I broke up, we’d gotten into kinkier fun, including group fun. We’d had a few threesomes with other men and women, but my favourite experience was my first ever gangbang.

We’d regularly go out to gay bars, with me fully feminised, and Rick, being the Adonis of a man he was, always got a lot of attention. We made a few good friends and fuck buddies from the gay bars and it’s where we found most of our group experiences.

I really enjoyed the attention I got from the guys too. I’d never had much luck getting female attention before I had my awakening with Rick, so having compliments on how good I looked and cute guys flirting with me was such a huge confidence boost I went a little mad with it.

I wanted to be used. I wanted all the dick I could get. One night after a fun threesome, I floated the idea with Rick that I’d like to have a big group to play with. He liked the idea too and said he’d work something out. Read more »

The time [m]y boyfriend watched [m]e get fucked by his best [m] friend while crossdressed

This came close to the end of Rick and mine’s relationship. We’d been together for a couple of years and we’d had a lot of fun, but the relationship wasn’t really going anywhere. But towards the end we’d gotten a bit more adventurous. We’d had a few group sessions, some really fucking filthy public sex and I’d gotten better with my cross dressing and makeup.

Rick hadn’t come out to his friends as bisexual yet. Our mutual friends knew we were a thing, but his friends from home didn’t know. He always referred to me as his girlfriend, which I was fine with, to be fair. One Saturday, he told me his best friend from school, we’ll call him James, was in town and they were going to meet up. James had also asked if he could meet the girlfriend he’d heard so much about. Rick, very sweetly, asked if I fancied meeting his friend in full drag. I said I’d love to. I asked him what he’d like me to wear.

“I don’t care, just look irresistible,” he said. My mind ran away with it, deciding on how to look. He told me they were meeting for drinks in the afternoon and to come meet them in the evening. Read more »

The time I [m] fooled around with my best friend/boyfriend [m] in my parents’ bathroom

Rick and I had been casually fucking for a couple of weeks. He’d known my family for quite a while so he was frequently invited to Sunday dinner with my parents. He actively looked forward to it, it was one of the rare occasions where someone fed him. And boy, could he eat.

On this particular Sunday, we’d spent the previous night together, which had gotten rather messy. In a haze I woke up, alone: I looked at the clock on his nightstand, it was already noon. “FUCK!” I thought to myself. I launched out of the bed and sprinted to my room completely nude and grabbed my phone. I hastily found my Mum’s phone number and dialled

“Oh, hello Mark (not my real name)” she said, answering after a couple of rings, “is everything alright?”

“Yeah, everything’s fine Mum” I panted, trying to stave off the dizziness of a head rush, “I’m just calling to let you know me and Rick will be a little late. I-”

Before I could finish she cut me off with a little laughter Read more »

My first cross dressing experience led to my first gay experience [MM]

This happened quite a few years ago when I was 19. Up until this event, I was pretty bi-curious but, coming from a small country village, didn’t have the means or ability to explore that curiosity. This happened my first year at uni.

I’d done my best from starting at Uni to be a social butterfly. I accepted any and all invites to party, spent probably far too much time in the pub and I made a lot of friends. There was one, we’ll call him Rick, who I was especially enamoured with. He was tall, muscly, with a little chin beard and long hair. We struck up a great friendship but I never had the courage to tell him just how attracted to him I was. I, for the sake of comparison, was a clear 6 inches shorter than him, rather slim and basically his exact opposite. Read more »