After indulging my fantasies of nylons, lingerie and heels on my own for some time, I decided to be brave and see if I could be ‘used’ whilst dressed in my girly clothes. I’m not a convincing CD, so I wasn’t going to hit the streets looking for attention, so I decided to see what happened on one of my business trips, which seems to be a standard approach for discreet crossdressers.
As I travel for work, I will often bring some of my girly clothes with me, so I can dress and do solo photoshoots in the privacy of my hotel room. On one of these occasions, I’d checked into my hotel in Bath, showered and shaved and then slipped into my black hold-up stockings, white silky g-string, white lace bra and finished off with a black figure hugging top and a brown leather pleated skirt. I finished it off with my high heeled black stilettos and took a few photos. All the time I was taking the photos, I was wishing a guy was there to explore me. Anyway, to finish off the photoshoot, I swapped my stilettos for a pair of black leather over-the-knee boots and clicked some more photos. Once I’d done this, I reluctantly removed my boots, skirt, top and bra and put on a shirt and chinos and shoes and went to the bar for a drink and a snack. On reaching the bar it was fairly quiet, just two tables taken, so I sat at the bar. I’d finished my first drink and ordered my second before another guest walked in and sat at the bar near me. He ordered his drink and then started to talk to me about the weather, the hotel, Bath etc. Whilst we chatted, he got my interest as he didn't seem cocky or obnoxious and was smartly dressed.
I wasn’t that hungry, so rather than go to the restaurant, I just had a club sandwich in the bar with my new acquaintance. As the night rolled on, I’d left the bar to go to the loo a couple of times and on the third visit to relieve myself, my acquaintance came with me. As we entered the gents, he blurted out
‘I love your thong. If there’s more to see, I’d love to get a view of that too’.
I blushed and replied that he was naughty for saying that, but yes there was more to see under my clothes. He watched me pee and I watched him and his average sized cock visibly grew as we chatted at the stalls. As we washed our hands, I said, coyly:
‘We can chat about what you’ve seen over another drink in the bar, then if you’re interested in seeing more, we can get a nightcap and take it to my room’. He smiled and agreed and we returned to the bar to get another drink.
On returning to our seats, I explained that what he’d seen was only part of what I’d been wearing earlier and that I’d had a photoshoot. He said we was intrigued and he’d love to see the photos to see what I was wearing. I responded by telling him what the outfit was like and that if he wanted to see it, it would have to be in person. His eyes lit up and said he’d love to. So we finished our drinks and I went up to my room to slip into my sexy girly outfit, whilst he waited 15 mins before bringing up a nightcap.
I sat on the edge of the bed nervously waiting for a knock at the door. Eventually, I heard footsteps in the corridor followed by a gentle tap at the door. I gingerly walked over to the door in my stilettos and opened the door slowly. In he walked with the drinks and put them down on the table in the room, ‘Oh my god’, he said, ‘you look fantastic. I just want to caress you and slip my hand under your skirt’. I couldn’t believe I’d made him react this way, it was so horny. So I replied, ‘Well why not come over here and show me?’
He slowly walked towards me and placed his hands either side of me on my waist. He then leant and and gently gave me a kiss on the lips, which took me by surprise as I’d never been kissed by a guy before. It set off strong emotions, so to signal that he could carry on, I returned the kiss, at which point he opened his lips and we kissed with tongues. I felt so energised and emotionally charged by this and could feel my legs shaking with excitement and trepidation. Whilst he was kissing me and one of my hands rubbed the bulge in his trousers, his hands had drifted to my leather clad ass, which he masterfully stroked and groped, generating new sensations in me and after a while one of his hands dropped down the front of my skirt to my holdup stockings. Here he stroked my legs in turn and rode his hand up to my stocking tops before continuing to the ever growing bulge in my g-string. This was another lovely sensation that saw my cock harder more than it had ever been before. The anticipation of what may come next only added to the sensation and I felt my breathing becoming faster and louder. He certainly knew what he was doing as he sank in front of me to his knees, with one hand stroking my legs and the other lifting the hem of my skirt. The hand that was stroking my leg was now stroking my cock through the shiny fabric and his other hand let go of my hem to grope my bare ass. I lifted my skirt to see his hand rub the front of my g-string and then he leaned forward to kiss and suck my hard cock through the fabric. This was mind-blowing. I was feeling so many emotions and had no time to rationalise them. The hand stroking my cock had moved back to my legs and the hand on my ass moved to the front and carefully slipped in my g-string to partially free my willing cock. He then did something that I’d always wanted to happen, which was lean forward and kiss my cock before partially swallowing it. His head bobbed up and down a few times, before he pulled away, rose to his feet and kissed me with immense passion. This took me to another level as I tasted my own pre-cum on his tongue and lips.
Things had really taken off, more than I could imagine and it was time for me to step up and pleasure him. I immediately sank to my knees and undid his belt and trousers, slipping my hand in to grope his bulge before leaning forward to kiss his cock through the fabric of his briefs. I was going to waste no further time as this was my chance to get a cock in my mouth, so I quickly removed his trousers, briefs, socks and shoes, revealing his reasonably sized, clean shaven cock (maybe up to 6’’) and balls, whilst he removed his shirt to reveal an average, but smooth body. I couldn’t hold back and took hold of his balls and leant forward to kiss, lick and suck them, then proceeded to lick up his shaft whilst massaging his balls. I slowly progressed to the tip, then took his cock with my hand and guided it to my willing and enthusiastic mouth. I licked the pre-cum and savoured it before engulfing his cock, with my mouth and really gave it a sucking like any girl would. After several minutes of doing this, he pulled away as he was concerned he may come. I smiled at him, rose to my feet and kissed him passionately whilst gently tickling his cock. Not wanting to lose momentum, I asked, ‘Would you like to 69?’, to which he replied, ‘ For sure’. He took me by my hands and carefully pushed me back to the bed where he got to his knees to start on my cock with his mouth again, whilst stroking my thighs with my legs draped over his shoulders. This was incredible and made me feel vulnerable and in control at the same time and I started to feel my sap rise, so I gently pulled away and pulled him on the bed next to me. We kissed, then I spun around and lay on top of him, so that we could take each other’s cocks in our mouths. I got to work on him and he sucked me expertly whilst stroking my nylons with one hand and my leather-clad ass with the other.
