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I had finished work feeling frustrated and bored so headed to the phone chatline. After chatting with several callers one called Terry kept responding and I did feel an attraction developing. His voice seemed rather gruff and I took him for a workman, someone who had an early start and finished work early and in need of some relaxation. I agreed to come to his address straight away - he was vague on what specifically he wanted (which was often a red flag) but seemed genuine enough so I decided to take a chance. I drove to his inner city address which was a ground floor flat on a social housing project. Terry opened the door - he was a burly guy with white curly hair - thick set, clean shaven and had a strong body. He smelled strongly of after shave as if he had just taken a shower. He had asked several different questions so I wondered what he was up for - one intrigued me - "Do you ever wear women's clothing?" towards the end. He didn't seem to want to kiss so I made my way into his living room which was quite sparse just a TV, sofa, cupboard with drinks etc - the whole flat seemed rather small.
I made to sit on the faded sofa and he said "No - not here....." So still standing I thought I better get to the point - "what do you us to do?" He then said "We go to the bedroom and sort it out there" so we went there - I was concious I needed to freshen up if we were going to get it on but he seemed insistent. When we got to the bedroom he said - "You wear women's clothes do you?" and seemed quite intense. Truthfully I hadn't so far but the idea did get me excited so I said "Yeah - no problem". He seemed to relax at that and then turned a sidelight on by the bed which had a red glow from a coloured bulb and then pulled out an old dusty suitcase. Opening it up there was a selection of women's lingerie inside and appeared to be a quite a jumble of colours, sizes and types. He then said "Sort through and find what you need - I'm going to the living room - call me when you are ready and close the door". He put a bottle of poppers on the bedside drawers and then left calling out "wear the wig". First off I went to the bathroom and then when I came back I sorted through the jumble trying to find things that were my size and matched. Finally I settled on a pair of black stockings, a half basque with suspender straps and some sheer red pantie thongs. And of course to top it off there was a bottle blonde wig which seemed rather course. Looking at the rest of the lingerie it was a mixed bag and some panties with old semen stains on. I checked myself in the mirror and it seemed to go together very well and looked sexy if I say so. I opened the door a crack and called out ready - hearing the sounds of a football match from the living room and closed the door, my heart beating anticipating what was to come.
Terry came back in and took in the view and seemed to approve his eyes roaming over the flesh on display. He then stripped out of his clothes right down to his garish boxer shorts which were hanging beneath his beer belly. I was pleased to see there was a stiff bulge in them already so fun was about to begin. He then pulled those down and out sprung an uncut hard cock, rather thick and about 6" so not too long. The head was starting to appear from the ring of thick foreskin around the edge. He then came close and started to pull down the top of the basque and kiss my nipples urgently which was very sexy and got me even more aroused. He then said "Lie on the bed" which i did but he didn't make any move to join me. Instead he lent over the bed and pushed his cock towards my lips. I started sucking on it - by now the head had erupted and worked all the way to the base with my nose in his pubes. He started pushing it in and thrusting and feeling the stockinged legs - that seemed to get him even more excited. At the same time he twisted the top of the poppers bottle and took a sniff. He then withdrew and told me to take the panties off and show him my ass.
Then he asked me to stand up and pushed me down by the shoulders and obviously wanted more oral sex. Again I started licking and then sucking his cock as he took more poppers. I sensed he was getting tense and his breathing increased - surely his orgasm was close - I sucked more urgently and soon he started groaning loudly jetting salty spray and there seemed lots of it ino my mouth. He picked his clothes up and as he went to leave the room he said "Finish yourself before you go....". Well I was still feeling very horny and looking at my state in the bedroom chest of drawers with hardon proudly displayed between the basque and stockings my hand started move backwards and forwards more urgently over my erect cock in the cheap red glow. As I was coming close to orgasm and the edge was approaching I looked again in the mirror which I was facing in my highly sexed state with heart pounding. I noticed the door was now quietly ajar and I could see the outline of Terry watching from the hall in the shadows. That carried me over the edge and I started spurting ropes of cum as the handwork got more urgent. Taking the clothes off and putting them in the suitcase and then changing back into my work clothes I felt more normal but it had been quite a new experience and wondered if I would do that again. Neither Terry and I seemed interested in exchanging numbers so as I left i knew that's where it finished.