I suppose I should start by giving you a bit of background on myself. I'm 28 and I've been with my 21-year-old girlfriend, Camila, for just over a year. I'd enjoyed dressing up in women's clothing since my early teens but I'd often go through long periods where I wouldn't be able to do it, usually because my girlfriend at the time wouldn't be okay with it. Luckily, Camila was more than okay with it. In fact, she seemed to really enjoy it. I wasn't even sure how I was going to bring it up to her at first, but when she found my hidden stash of clothing I didn't have much choice but to explain everything. I couldn't exactly let her think they belonged to some other woman I was cheating on her with.
She sat there for a minute or so, looking between me and the bag of clothes she'd found, with a thoughtful look on her face. I could see the cogs were turning in her mind and I was beginning to resign myself to the fact that she was probably about to leave me. A smile suddenly appeared on her face and she started rummaging through the bag. She pulled out a red satin and lace babydoll which just so happened to be one of my favourites, threw it to me and told me to put it on. After that, we had sex and now we often incorporate my dressing up into our sexual activities.
It wasn't until my early twenties that I realised I was bisexual. I'd always thought I just liked girls up until that point, although I'd never actually done anything with one as I was pretty awkward in my teenage years. I'd started to fantasise more and more about guys and my first sexual experience actually ended up being with a guy. We connected after I'd posted online about wanting to try giving a blowjob to a guy. We then met up in a field at night time with nobody else around. Surprisingly, he said I was really good at it considering it was my first time. I don't know whether he was just saying that to be nice or not but it made me feel good. He ended up finishing on my face as I definitely wasn't ready to take it in my mouth with my first blowjob.
There were two other guys I met up with. The first picked me up in his car, then we drove somewhere secluded and sucked each other off. I came in his mouth but I still wasn't brave enough to let him cum in my mine. The second guy came over to my flat and I let him lay me down on my bed and fuck my throat. He came on my face and chest to finish but a drop or two landed on my lip so I tasted it and immediately regretted not having let him finish in my mouth. I loved the taste and wanted to kick myself for not trying it sooner. In between these two guys, I also met a transgender woman. She was the first person who ever fucked me, which she did so on the stairs in doggy position and then on her bed in doggy and missionary.
Okay, so that's enough background. Some university friends of Camila's had invited us both to a Halloween party they were throwing. At first, I was just going to go as a generic vampire or something along those lines. Eventually, she convinced me that it would be a great opportunity to crossdress in public for the first time as who was going to look twice when it was Halloween? I decided to go as Anna from Frozen since I already had her full outfit including a ginger-haired wig with pigtails. Once I had dressed up, Camila did my makeup for me. I'd tried a couple of times before with makeup but I could never get it to look good. I took a look in the mirror and even I couldn't recognise myself. I loved it. Cami chose to go as Wednesday Addams. She already had the long dark brown/black hair so all she had to do was put on some black clothes, long black boots and make herself look pale.
The party was only a few streets away so we walked there. I was nervous stepping outside at first, but she took hold of my hand and this helped a little. Once we got to the party, Cami's friends greeted us with hugs and showed us in. We moved into a large kitchen/dining area with a table in the corner full of alcohol and people spread throughout, talking to each other, dancing and a few even making out. I was shaking a little, convinced that nobody was fooled by my outfit. Camila must have seen this as she took my hand in hers with a little squeeze and led me over to the table full of drinks where she poured a shot of something,
"Drink this, it'll help with your nerves." she said, handing me the shot glass.
I drank the shot, grimacing as I swallowed. Camila giggled at my reaction. Whatever it was, it was strong. It didn't taste great, but it did seem to calm my nerves just a little bit. After a few more shots of various other liqueurs, I was barely even thinking about it anymore, so we poured ourselves a rum and coke each and moved towards the middle of the room to dance. I forgot sometimes how good of a dancer she was. She was certainly getting looks from some of the guys and even a few of the girls too. We were just finishing our drinks when a small group of people came into the room. Camila noticed them come in, downed what was left in her glass and leaned over so her mouth was next to my ear.
"I'm gonna go see a couple of my classmates down the hall, will you be alright by yourself for a bit?" she asked. I nodded in reply. "Okay, just have another drink and talk to people, yeah? It will make you more confident." With that, she hugged me, kissed me on the lips and left the room. I took a deep breath and went to go make myself another drink. I'd just started pouring it when I heard a voice behind me.
"Wow, I love Anna!" I turned around, it was a guy from the group of people that came in just before Camila left. He was about the same height as me, with an average looking build in the top half but I could see he had some pretty thick thighs and calves, I would guess he probably cycled a lot or played some sort of sport and he was wearing a Kristoff outfit. Anna's boyfriend, small world! He was looking me in the eyes with a slight smile on his face.
"Hi..." was all I managed to get out as I felt my face flush. Kristoff chuckled.
"So what's Anna's name when she's not being Queen of Arendelle?" he asked as I fiddled with the straw in my drink. I almost replied with my actual name before I caught myself just in time. That would have been a disaster. I hadn't actually chosen a name for myself for when I'm dressed up, so I stood there for what felt like ages trying to come up with one before I realised I had to say something before he thought I had forgotten my name.
"...Emma!" I blurted out. I guess there are worse names I could have come up with but I'd never really thought about it before now. But, now that I had, I had always felt that Emma was a cute name.
"Well, Emma..." he began as he poured himself a drink. "I'm Mike and I would very much like to dance with you if you wouldn't mind?" He offered his hand to me. I thought for a few seconds. It might have been a bit of a cheesy line but I was very flattered so I put my hand in his and he gently led me towards the other dancers in the room. I've never been a good dancer, not even close. So, of course, I danced really awkwardly. Mike didn't seem to mind but I knew I'd need more drink in me before I'd be loose enough to at least not care about how bad I was dancing. Once the current song ended, I left him talking to a couple of his friends while I went over to have a few shots and make myself another drink.
Just as I'd finished making my drink, my favourite song started playing. My eyes widened and a combination of the song playing and the alcohol sent me scurrying back to Mike, drink in hand. I danced and sang along to the song and I could finally feel myself loosening up. My inhibitions had definitely been lowered as well; I was dancing a lot closer to Mike and even touching his arms and chest now and then. A couple more shots later and my arse was firmly planted in his crotch and my arm around his neck, pulling his head close to mine as we danced. His hands moved to my thigh and stomach and I felt him pull me into him even more. Mike's breathing on my neck sent a tingle through my body that I would never have expected. My breathing quickened a little and I found myself, almost unconsciously, moving his head closer to mine and turning mine to meet his.
I looked into his eyes for a good ten seconds or so. It felt for a moment like everything went quiet and nobody else was in the room except for him and me. He moved so that his lips were barely an inch away from mine like he was testing the waters, seeing if I was up for it or not, letting me make the first move. So I did. I kissed him. And it felt amazing. His lips were soft, he used the perfect amount of tongue and I felt a warm wave of pleasure wash throughout my whole body. Mike broke the kiss off and I was suddenly back in the room again, aware of everyone else in the room. Nobody was paying any particular attention to us though.
She sat there for a minute or so, looking between me and the bag of clothes she'd found, with a thoughtful look on her face. I could see the cogs were turning in her mind and I was beginning to resign myself to the fact that she was probably about to leave me. A smile suddenly appeared on her face and she started rummaging through the bag. She pulled out a red satin and lace babydoll which just so happened to be one of my favourites, threw it to me and told me to put it on. After that, we had sex and now we often incorporate my dressing up into our sexual activities.
It wasn't until my early twenties that I realised I was bisexual. I'd always thought I just liked girls up until that point, although I'd never actually done anything with one as I was pretty awkward in my teenage years. I'd started to fantasise more and more about guys and my first sexual experience actually ended up being with a guy. We connected after I'd posted online about wanting to try giving a blowjob to a guy. We then met up in a field at night time with nobody else around. Surprisingly, he said I was really good at it considering it was my first time. I don't know whether he was just saying that to be nice or not but it made me feel good. He ended up finishing on my face as I definitely wasn't ready to take it in my mouth with my first blowjob.
There were two other guys I met up with. The first picked me up in his car, then we drove somewhere secluded and sucked each other off. I came in his mouth but I still wasn't brave enough to let him cum in my mine. The second guy came over to my flat and I let him lay me down on my bed and fuck my throat. He came on my face and chest to finish but a drop or two landed on my lip so I tasted it and immediately regretted not having let him finish in my mouth. I loved the taste and wanted to kick myself for not trying it sooner. In between these two guys, I also met a transgender woman. She was the first person who ever fucked me, which she did so on the stairs in doggy position and then on her bed in doggy and missionary.
Okay, so that's enough background. Some university friends of Camila's had invited us both to a Halloween party they were throwing. At first, I was just going to go as a generic vampire or something along those lines. Eventually, she convinced me that it would be a great opportunity to crossdress in public for the first time as who was going to look twice when it was Halloween? I decided to go as Anna from Frozen since I already had her full outfit including a ginger-haired wig with pigtails. Once I had dressed up, Camila did my makeup for me. I'd tried a couple of times before with makeup but I could never get it to look good. I took a look in the mirror and even I couldn't recognise myself. I loved it. Cami chose to go as Wednesday Addams. She already had the long dark brown/black hair so all she had to do was put on some black clothes, long black boots and make herself look pale.
The party was only a few streets away so we walked there. I was nervous stepping outside at first, but she took hold of my hand and this helped a little. Once we got to the party, Cami's friends greeted us with hugs and showed us in. We moved into a large kitchen/dining area with a table in the corner full of alcohol and people spread throughout, talking to each other, dancing and a few even making out. I was shaking a little, convinced that nobody was fooled by my outfit. Camila must have seen this as she took my hand in hers with a little squeeze and led me over to the table full of drinks where she poured a shot of something,
"Drink this, it'll help with your nerves." she said, handing me the shot glass.
I drank the shot, grimacing as I swallowed. Camila giggled at my reaction. Whatever it was, it was strong. It didn't taste great, but it did seem to calm my nerves just a little bit. After a few more shots of various other liqueurs, I was barely even thinking about it anymore, so we poured ourselves a rum and coke each and moved towards the middle of the room to dance. I forgot sometimes how good of a dancer she was. She was certainly getting looks from some of the guys and even a few of the girls too. We were just finishing our drinks when a small group of people came into the room. Camila noticed them come in, downed what was left in her glass and leaned over so her mouth was next to my ear.
"I'm gonna go see a couple of my classmates down the hall, will you be alright by yourself for a bit?" she asked. I nodded in reply. "Okay, just have another drink and talk to people, yeah? It will make you more confident." With that, she hugged me, kissed me on the lips and left the room. I took a deep breath and went to go make myself another drink. I'd just started pouring it when I heard a voice behind me.
"Wow, I love Anna!" I turned around, it was a guy from the group of people that came in just before Camila left. He was about the same height as me, with an average looking build in the top half but I could see he had some pretty thick thighs and calves, I would guess he probably cycled a lot or played some sort of sport and he was wearing a Kristoff outfit. Anna's boyfriend, small world! He was looking me in the eyes with a slight smile on his face.
"Hi..." was all I managed to get out as I felt my face flush. Kristoff chuckled.
"So what's Anna's name when she's not being Queen of Arendelle?" he asked as I fiddled with the straw in my drink. I almost replied with my actual name before I caught myself just in time. That would have been a disaster. I hadn't actually chosen a name for myself for when I'm dressed up, so I stood there for what felt like ages trying to come up with one before I realised I had to say something before he thought I had forgotten my name.
"...Emma!" I blurted out. I guess there are worse names I could have come up with but I'd never really thought about it before now. But, now that I had, I had always felt that Emma was a cute name.
"Well, Emma..." he began as he poured himself a drink. "I'm Mike and I would very much like to dance with you if you wouldn't mind?" He offered his hand to me. I thought for a few seconds. It might have been a bit of a cheesy line but I was very flattered so I put my hand in his and he gently led me towards the other dancers in the room. I've never been a good dancer, not even close. So, of course, I danced really awkwardly. Mike didn't seem to mind but I knew I'd need more drink in me before I'd be loose enough to at least not care about how bad I was dancing. Once the current song ended, I left him talking to a couple of his friends while I went over to have a few shots and make myself another drink.
Just as I'd finished making my drink, my favourite song started playing. My eyes widened and a combination of the song playing and the alcohol sent me scurrying back to Mike, drink in hand. I danced and sang along to the song and I could finally feel myself loosening up. My inhibitions had definitely been lowered as well; I was dancing a lot closer to Mike and even touching his arms and chest now and then. A couple more shots later and my arse was firmly planted in his crotch and my arm around his neck, pulling his head close to mine as we danced. His hands moved to my thigh and stomach and I felt him pull me into him even more. Mike's breathing on my neck sent a tingle through my body that I would never have expected. My breathing quickened a little and I found myself, almost unconsciously, moving his head closer to mine and turning mine to meet his.
I looked into his eyes for a good ten seconds or so. It felt for a moment like everything went quiet and nobody else was in the room except for him and me. He moved so that his lips were barely an inch away from mine like he was testing the waters, seeing if I was up for it or not, letting me make the first move. So I did. I kissed him. And it felt amazing. His lips were soft, he used the perfect amount of tongue and I felt a warm wave of pleasure wash throughout my whole body. Mike broke the kiss off and I was suddenly back in the room again, aware of everyone else in the room. Nobody was paying any particular attention to us though.