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Sissy Boy Wimp Pt 3

"My wife encourages my bisexuality but with a surprise!"

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After Mark had left and both myself and my wife had recovered, we had a bit of a discussion about what was happening to both of us. She asked if I liked what had happened to me up to now, and I had to confess that I had enjoyed it. This must have pleased my wife as she smiled and then asked me about Mark and about her letting him do those things to me. Again, I said okay without wanting to sound too enthusiastic.

Up to my feminisation I had never considered that there might be a gay gene in me but events of the last few weeks had opened my eyes. Wearing panties and feminine clothes made me think differently. I had started to consider things from a more girlie perspective, and I had to admit that what Mark did to me was not unpleasant, in fact, I had quite liked it. There was more to sex than I had realised.

By the middle of the following week, my wife asked me if I would like to meet Mark again. She said it in such a way that it wasn’t worth my while refusing, so I agreed. The truth was that I had been looking forward to a repeat encounter. She then handed me a piece of paper with his address on it and told me that I was to knock on his door the following night after work with everything I needed to feminise myself with. She said she trusted me to do as I was told.

As you can imagine I was shocked. I couldn’t speak for quite a while and when I did she wouldn’t tolerate an argument and that I was to do as I was asked. She also said that while I was at Mark’s she would be out with a new friend she had met and that I was to ring her when I was about to come home.

The following day was full of trepidation. My girlie things were packed into a holdall and put into the boot of my car and I went to work. I was both nervous and excited about going to Marks's house but my level of concentration doing my job, suffered that day.

Finally, after work, I knocked on Mark's door. As he opened it, I could only see his head peering around looking a little nervous. The door was opened so as to invite me to enter but Mark remained behind it until I was over the threshold. As he began to close it behind me I could clearly see why he didn’t want to be seen before the door was closed. He was dressed as feminine as I had been these last few weeks. All that was missing was a wig to cover his short-cropped hair which he very quickly put on.

He led the way to the lounge area and I followed. I must say his deportment was very good. From behind you couldn’t tell he was male. He had the walk of a woman and I noticed that the voice was different too. Handing me a glass of wine he explained that I was to go upstairs, shower and dress and then we would have dinner and chat before we made ourselves more comfortable.

Twenty minutes later dressed in a light green mini skirt with a white sleeveless top I emerged into the lounge. My black stocking tops were visible below the hem of the skirt which indicates how short the skirt was. With make-up and a little jewellery as well as a pair of black sheer panties my outfit, chosen by my wife, was complete.

Mark, on the other hand, was wearing a sleeveless red dress that flared out from the waist to just above his knee. He also wore a pale cream shawl to cover his bare arms and shoulder. Again black stocking covered the rest of his legs showing below the dress and his make-up was expertly applied.

We sat and ate dinner. During the course of our conversation, he told me he wanted to be called Maria and asked me about my feminine name. I didn’t have one as my wife always referred to me as "Sissy-Boy." Sissy it was. We both began to refer to ourselves with our feminine names and gender and Maria explained to me what my wife expected of me.

It appeared that I was there to do to Maria what Maria did to me the other weekend. My wife wanted to know if I could give as well as take. This was not the woman I married all those years ago. Where did all this come from?

Maria explained to me that at work they had little by little discussed the frustration my wife felt about my lack of assertion and my lack of sexual performance. I was shocked and hurt. Maria said that many of the magazines that she had been reading had added to her frustration and many of the articles claimed she was missing out if she wasn’t experiencing a broad sex life.

My wife, it appeared, had closely questioned Mark/Maria about his lifestyle and had been intrigued by it and how much pleasure he got from it. She had, apparently, decided that her wimpy husband should explore the more feminine side of his nature and that convention would be thrown out. From now on there would be no rules. After my experience of the last few weeks, I was all for that but did wonder what my wife was getting from all this.

Meanwhile, Maria took me by the arm and led me to the couch, and made us both comfortable. With her arm around my shoulder and my hand on her leg, we relaxed. Well, Maria relaxed, I was nervous but excited. More small talk and suddenly we were kissing, our hands exploring each other's bodies, caressing and fondling until all my nervousness had disappeared.

It wasn’t long before I was fully aroused and my hands were up Maria’s skirt and fondling her bottom and trying to nuzzle my head under the skirt to clasp my mouth around her cock. Once I had achieved this Maria gave in to me and let me do whatever I wanted. What I wanted was to do as my wife had asked but personally to do to Maria what Mark had done to me.

Her panties had to go, so grasping the top of them round her waist I slowly pulled them down over her bottom. I had to take my mouth away from her cock in order to lift the panties over the swollen obstacle, but only for a second before clamping it over her again. Meanwhile, with hands on either cheek, I began massaging them and pulling them apart little by little so that my entry point became more accessible.

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Maria reached behind a cushion on the couch and retrieved a tube of lube and a condom. She then reached down and grasped my cock, probably to see if I was hard enough, which I was. After giving it a few tugs she handed me the lube as she tore open the condom packet and adjusted herself to put it on me herself.

There’s something nice about letting someone fit a condom over your cock. The lovely feeling it gave me as it was gently placed over my sensitive member and the expectation both of us knew was going to happen. Maria slid off the couch and as she did so she turned so that her back was turned towards me.

By now I’m ready for my quest and very keen to complete the task my wife had given me. I did wonder if she thought I might be getting more pleasure out of it than she thought I should. The truth was that I probably did. I was more than ready to let Maria have it as I lifted her skirt over her bottom.

My finger ran down the cleft between her bottom cheeks and as the lube did its job I gently eased a finger into her and began to massage her hole. After a couple of minutes of Maria gently moaning I covered my condom-clad cock with plenty of lube and pushed the tip of it to the entrance I had been exploring. Little by little I entered her and was delighted with the warmth and snugness of it. This wasn’t going to last very long at all.

Determined not to cum too quickly I slowed down and took my time sliding in and out of her. The sensation was ecstatic. The sight of two female-clad individuals wrapped around each other clamped by the hips must have looked like a lesbian orgy but I didn’t care as I could only concentrate on trying to make it last.

It was a losing battle and I couldn’t stop myself from quickening the pace, very soon reaching the point of no return. My eagerness overtook and I pumped away at Maria until all consideration for her left me and I thrust myself into her with abandon and very loudly cumming. Slumping over Maria I left myself inside her for as long as possible until I could breathe more steadily.

As my cock softened and eventually slipped out of her I suddenly thought about Maria and whether I had hurt her. I needn’t have worried though she did jokingly say that she might not be able to sit down for a while. I also thought about my wife and how pleased she would be about me completing my task.

Maria brought me back to life as she said it was time for her reward. With that, she lay on her back and presented me with her cock. I knew instantly what she wanted and despite it not being one of my wife’s direct instructions other than to do as I was told, I once again clamped my mouth over her cock and began licking and sucking on it for all I was worth.

I licked and sucked on her for ages and was really enjoying it when her body started to stiffen and I knew she would cum very soon. I was determined that I was going to take it all and pursed my lips more tightly over her cock. This made her thrust deep into my mouth and I thought I would retch but I had other things to consider as she exploded into my mouth. Now it was a struggle to swallow it all without choking.

Pleased with myself I gave her a kiss so that she could taste herself on me and we draped ourselves over each other and recovered.

The evening over, we chatted as we changed into our male attire, both of us leaving our female panties on. During the course of our chat, Mark wanted to know how much I had enjoyed it for its own sake and not just about doing as I was told.

I had thought about this and I would never have considered it before my wife led me to being feminised. Now that I was introduced to a new sexual world I wanted it. Cock or pussy I didn’t care. I had my wife’s permission to enjoy it and the more I experienced this world the more I wanted it. If all I had to do was to endure being called a “Sissy Boy” in order to taste this new sexual freedom. Then so be it.

At the back of my mind, I had wondered what my wife’s motives had been for my feminisation. She had been the biggest part of my new sexuality and had enjoyed my participation with other men. It also occurred to me that her using the dildo on me was a way of belittling me. I couldn’t work out where all this was going. Secretly I didn’t want it all to end. Was it part of her plan to take it all away at the point I was really enjoying it? Once home I needed a talk with her to see if she was okay with that.

As I opened the front door I could hear more than my wife’s voice, so quickly turned to the mirror in the hall to check if I still had any makeup on. Making sure I hadn’t, I entered the lounge only to be met by my wife sitting very close to another lady who was introduced to me as Maureen. I was very quickly informed that Maureen was staying the night and that I would be staying in the spare room and I should go and put the kettle on and make them a cup of tea.

With that, I left the room as they stroked each other's bare legs, I noticed neither of them was wearing any tights, and they giggled away at my situation while giving me orders.

In some ways, I giggled about my situation too but was not exactly clear about what it was. Had my wife converted me to bisexuality only to inform me of hers? If she didn’t mind me cross-dressing and having sex with other men, then how could I possibly object to her having sex with another female? She probably thought I had no choice but to accept it, that she had so much on me that I couldn’t possibly object.

Well, she was right but I didn’t really care. She had introduced another side of life to me and one I’m going to wholeheartedly embrace. In fact, I’d arranged to meet Mark/Maria again the next week, and as it happened when my wife was meeting Maureen.

Happy days!

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Written by spenny134
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