In my last story, I ended it by mentioning that I had been given an ultimatum from a contractor who had seen Mark and I intimate in my back garden. The contractor had been fitting wardrobes in a house at the back of mine and had watched us having sex on a sun lounger in my garden. Later that day, he had come round to my house and told me that he expected servicing if he was to keep quiet about what he saw. He said he would be round for his reward every lunchtime whilst he was doing the job. Before leaving, he made me give him a blow job and told me to dress slutty the next day. This story is what happened next.
I awoke the next day thinking of Mark and then my lovely thoughts came crashing down when I remembered the encounter with the contractor the previous evening. I showered and dressed and did the usual preparation for when I was meeting a guy, to make sure I was perfectly hygienic. As usual, I was working at home, so I thought I’d leave the slutty outfit until closer to lunchtime. To start the day, I just wore a light brown short bodycon dress, white lace underwear, black 20 denier tights and beige knee high boots with a 4” heel. Although it was just me at home, I wanted to feel girly all day, so that I was better prepared and ‘in character’ for when the brute of a contractor came around. My office is in one of the bedrooms at the back of the house, so I kept looking out to try to work out which house the contractor was working at. Later on, when I went down stairs to make a drink, whilst the tea was brewing, I went out on the patio to try to see which house would have had a view of my sunlounger. I sat down on it and narrowed it down to two possible houses and kept looking for movement. I guessed it was the one with all the upstairs windows open and after satisfying my curiosity, I went back in to the house, got my drink and returned to my office. Once I was back at my desk, I received a message from an unknown number. I opened it and realised it was from the wardrobe guy,
‘You’re looking sexy and sophisticated today, Joanna, but I want you dressed like a slut when I come round at lunch, Gary’. So, I now knew his name.
I replied with, ‘Oh, yes, Gary, I remembered, I’ll get changed before you come, I didn’t want to spoil the surprise x’
‘Good slut’, was his reply
I got back to my work and, at around 12:15, I received another text saying, ‘I’ll be at yours in 30 mins’. I took this as a hint to go and get ready.
I went to my room and selected the outfit I was going to wear. I stripped off my clothes and went for a quick shower to freshen up. Once dry, I selected the stockings which were 15 denier in glossy black. Once they were on, I pulled on a black wet look bra and matching thong, then slipped on my new thigh high black PVC boots with 5” stiletto heel. I looked in the mirror and thought that I looked fairly slutty, but chose to finish it with a black, wet look long sleeve micro bodycon dress with full zip at the front. The dress truly was ‘micro’ length, as it barely reached my stocking tops, after doing my make up and applying bright red lipstick, I put my wig on and sprayed some perfume. I made sure the lube and condoms were ready, then I had a few minutes before Gary would arrive, so I went down stairs to get a glass of water, full of trepidation.
Just as I poured my water, there was a knock at the door. I took a few deep breaths and went to open it.
‘Fuck me, you have nailed the slut look’, he said as he walked in and squeezed my ass. I closed the door and turned to him at which point he grabbed my face in his big rough hands and assaulted my mouth with his tongue, lowering one hand to rub my growing bulge. He stepped back and got his phone out to take some photos of me in different poses, then told me to take him to my bed. As I walked upstairs ahead of him, he shoved his hand up my dress. I couldn’t work out if he was unrefined or just overly enthusiastic.
On getting to my room, I showed him in and closed the door, then I went to stand next to the bed and wait for him to lead. Sure enough he did, pulling me to him and kissing me. His kissing was rough and desperate and he was breathing heavily. I reached down and rubbed his crotch and started to unfasten his work trousers. He carried on kissing me as he unfastened and removed his shirt at the same time. Once I’d got his trousers undone, I pulled them down to his knees with his underwear. He broke away pulled his work boots off and stripped off his trousers and pants and was just stood there in his socks. His hands were all over my dress and under it as he kissed me again. I just went with the flow and kissed him passionately and stroked his ever growing member and then I felt the usual pressure on my shoulders to get on my knees. On being a level with his cock again, I noticed more about it than the previous encounter, when he’d quickly forced me to suck his cock whilst still shocked from his ultimatum. This time I could appreciate what he had to offer and I started to enjoy it. He smelt clean and his cock felt soft and smooth. I went about my business and he just gently stroked my hair, occasionally thrusting his pelvis in my face. After stroking, licking and sucking him for some time, he told me to get up. I did as I was told and made to get on the bed. He lay next to me and kissed me again, whilst raising the hem of my dress. On reaching my thong, he quickly pulled it off and threw it on the floor and started probing my pussy with his finger. I opened my legs to give him easier access and he probed me deeper, whilst I stroked his shaft. Finally, the moment came where I had to give him what he felt he deserved, when he announced that he was going to fuck me. I reached for the lube and passed him a condom which he slipped on. Once I was lubed, I passed it to him and he lubed his sheathed cock. I was surprised when he knelt between my legs and lined up his member, as I assumed he’d want to roughly shag me on all fours. Maybe he wasn’t as unrefined as I thought! I relaxed and spread my legs further to facilitate his entry and he made contact with my lovehole, slowly slipping in and causing me to breathe heavily now. He proceeded gradually pushing in more until I could feel his pelvic bone push against me. Once he saw I was comfortable, he leant down and kissed me, which I actually enjoyed. He then broke from the kiss and began his attack on my pussy by pulling back until he was almost out and then using all of his weight to thrust back in, making me feel as though he was trying to break me. He carried on his pursuit of punishing me for my indiscretion the day before and pummelled my hole. He was rough, but I didn’t mind, as it just meant it would likely be over quicker. He was groaning, calling me a slut and a whore and telling me that I deserved to be used. It was actually quite a turn on to be treated this way by a guy I didn’t know existed less than 24 hours earlier. His breathing became noisier and he leant down to kiss me, before calling me a slut again and emptying his balls into the condom. I felt the pulse of his manhood spurting 6 or 7 jets of cum. As he softened, he pulled out and told me to sit up. As I did, he handed me the really full condom and told me to drink it. I wasn’t going to object, as I don’t like to see cum go to waste. I poured it in my mouth, swallowed and showed him my empty mouth. He smiled, as did I, as it tasted very pleasant.
‘So, this is working out well’, Gary said, ‘I’m glad I caught you in the act, otherwise I would have missed out on this treat’
I just smiled, there was nothing to say. He lay next to me and asked me all about my life as a crossdresser and my encounters with other guys. I told him highlights and explained that Mark, who he’d seen me with was my ‘affair’, who I saw with the blessing of my regular lover, Colin. He was amazed at my back story and the other guys that had used me and it all seemed to get him aroused again, so I started stroking his cock again, whilst recounting some of my experience. As he hardened he kissed me again and said, ‘Right, you can give me a blow job before I have to go back to work’. He got off the bed and stood next to it, so I got off too and knelt on the floor in front of him. I stroked his balls, licked his shaft and then set to sucking him again. He thrusted into my mouth and, basically, face fucked me. He was groaning and calling me a ‘useful slut’ whilst I was sucking and actually enjoying myself. Before long, my efforts paid off and I felt his cock pulse and he let out a loud groan. I felt the first jet of cum hit my throat, then he quickly pulled out and shot the rest on my face and my dress, which was another impressive amount. As the jetting stopped, I leant forward and sucked and licked again to make sure nothing was wasted. I thought to myself that he’s such a heavy cummer, I might get something good out of this arrangement! I scooped up as much cum as I could with my fingers and stared him in the eyes as I licked it and swallowed it. He got his clothes together and dressed and, when he was ready, I followed him downstairs. Once at the door, he turned, kissed me, groped my ass and told me to wear the boots tomorrow and to dress like a St. Trinian’s pupil.
He left and I was relieved it was over. At the same time, I was relieved it had gone so well. I actually realised that my girly cock was hard, so I went to my room, removed my dress and lay back on the bed, wanking, whilst thinking about what we’d just done, until I shot my load on my stomach.
I’ll pause there as I don’t want it to be too much all at once, so I’ll continue in Part 2 very soon.
Thank you for reading,
Joanna xx
