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.

I spent the day doing my normal hair removing routine, moisturising, hair & makeup, painting my nails and douching (not necessarily in that order). I knew Rick would be horny if he’d been drinking and I wanted to get fucked.

I tucked myself and then picked out a pair of cute, lace knickers, a lace bra which I filled with some breast forms, then a short blue velvet dress with a high neckline. I finished it off with a pair of above the knee leather boots with a nice high heel.

I walked into the pub and saw them in a booth far in the corner. Rick was laughing like a drain, he was quite drunk. James was less drunk, but on his way. He was tall, his head was shaved short and he sported a well maintained, slightly long beard. He was CUTE.

I sat next to Rick and gave him a quick kiss.

“James,” he slurred, “meet Mel, my girlfriend”
“Well aren’t you lovely?” James said, taking my hand and kissing it. I giggled, it felt nice to be completely incognito.

The boys ordered more drinks and the night was a lot of fun. I’ll admit, it was hard to maintain my femininity as I got drunker. I had to really concentrate on my voice to make sure it didn’t sound too masculine. When I needed to go to the toilet, twice I nearly walked into the Gents through force of habit.

As closing time approached, James suggested we go clubbing. Rick was pretty drunk but he was well up for it, so I agreed too. We found a club nearby and we hit the dance floor. I started to refuse drinks, deciding to keep my composure, but I really did enjoy the attention I was getting on the dance floor. Rick sat down and watched the scene as I danced with a couple of girls.

James came up and danced with me. He leaned forward and whispered (shouted) in my ear that Rick was a lucky man, that I was very attractive. I smiled coyly and didn’t say anything back to him. I could feel Rick’s eyes on us. I glanced over and he was smiling so I thought I’d tease him a little. I turned around and grinded gently against James. I glanced back at Rick and he was still smiling. James must have looked over at him too as I felt his hands come around me and touch against my stomach. I danced a little more provocatively, swinging my hips to the beat and pressing up against James’ crotch a little more. I could feel his bulge growing. I was getting a bit turned on myself.

After a little while, Rick stood up and walked over to us. He suggested we get a taxi and head back to his flat.

About half an hour later we spilled into his flat, a trio of drunken messes. The boys dropped onto the sofa and I went to the kitchen to get some beers from the fridge. As I came back to the living room, I caught the tail end of James complimenting Rick on how hot his girlfriend was.

“You have no idea,” Rick said as I walked in. I handed them the beers and James gave me a hungry look. I sat on Rick’s lap and crossed my legs, making sure James got a good look at my thighs. Rick was hard as a rock, I could feel his enormous bulge as I shifted to get comfortable.

“What I wouldn’t give for a woman like you,” James said directly to me.

“I’m not sure you could handle a woman like me,” I said, with a saucy tone. Rick laughed, and agreed.

“Oh please,” James said, “I bet I’m better in bed than anyone you’ve ever had”

“Oh really?” Rick said, still laughing, “what do you think, Mel, want to see what he’s made of?”

I felt a flutter of excitement in my stomach, “if you’re sure it’s okay,” I said, trying to hide my excitement and remain coy.

“Go on, then,” Rick said to James, “do your best. But I’m warning you, she’s full of surprises”

James didn’t need to be told twice. He stood up and unzipped his fly. He stood before me and gestured for me to reach in. I grabbed his firm bulge. I smiled and undid his buckle, allowing his jeans to fall to the floor. James unbuttoned his shirt while I released his hard cock from his boxer shorts. It wasn’t as big as Rick’s, but it was a good size. Unlike Rick, James was circumcised. I felt like a pornstar as I teased the head with my tongue. James let out a little moan as I opened my red lips and took his cock into my mouth.

I sucked hard. As hard as I did my first night with Rick. I swallowed that cock like it was the last cock in the world. Rick was loving it. I could feel his bulge pulsing and straining his jeans under my ass.

James put his hand on the back of my head to guide my motion but I swatted it away. Instead I dug my nails into his rock hard butt and forced my own head down his cock. He wasn’t moving at all but I was getting face fucked. Rick moved his hand up my skirt and touched my hard shaft that was, miraculously, still tucked between my legs. James’ legs were shaking and he said he was close, at which point I pulled my head off his cock and stopped touching him.

“What’s wrong?” Rick said.
“I want to be fucked,” I said between pants, “can he fuck me daddy?”

Rick loved it when I called him Daddy. I actually felt his dick jump.

“You wanna fuck her?” He said to James. James nodded.

“Okay, but I told you she’s full of surprises. Show him, honey.”

James watched in confusion as I stood up and turned away from him. I took off the dress slowly, revealing the back of my bra and my panties. I kept my boots on. I reached into my underwear and pulled my cock out, then I undid my bra and as subtly as I could, took it off with my breast forms.

“Are you ready for a surprise?” I said with the best sultry tone I could muster. James said he was. I turned around and he saw my thin, male frame, my smallish cock hanging out the top of my panties and my thigh high boots. “Surprise”, I said.

James was stunned into silence. He looked at Rick, then back at me, the back at Rick.

“I think you broke him,” Rick said to me.

“He’s still just as hard,” I said. I walked towards him and grabbed his rock hard cock and gently stroked it, “are you sure you don’t want to fuck my tight little ass” I said in my most feminine voice, before kissing him gently on the lips. That did it, he snapped out of it and kissed me back.

When we broke the kiss, I got on my knees on the sofa next to Rick. I kissed him as James pulled my panties down. Rick licked his fingers and pushed them into my ass. I moaned, as he loosened me up for his best friend.

“Please fuck me,” I said. James put one hand on my ass cheek, then slowly pushed his cock into my hole. It wasn’t as painful as when I fucked Rick, he was smaller and it didn’t take long before we were fucking at a good pace. Rick watched happily as his friend ploughed my ass.

Within minutes he was fucking me frantically. I was screaming and moaning, it was bliss. Rick has taken his cock out and started wanking at the sight of us. I tried to control the rhythm but James would slap my cheeks hard and kept going. He was giving me a proper pounding and I was loving it.

As he got closer to cumming, he grabbed my hair (my actual hair. I’d grown it out by this point. Wigs are itchy) and pulled my head back. This brought me over the edge and I leaked cum all over the sofa. He grunted loudly, his cock swelled and he slid out of my ass, cumming all up my back and into my hair. His twitching cock then rested in my ass crack as it continued to leak drops of cum.

Rick reached his peak and turned on the sofa, aiming his dick at me. He came over my arm, up to my shoulder and the side of my face as I gathered my breath.

It was a fun night all round.

Source: reddit.com/r/gonewildstories/comments/flel2r/the_time_my_boyfriend_watched_me_get_fucked_by