My Cross Dressing Awakening Ch. 02

Chapter 2

My relationship with Fia continued for a number of years. Over time we progressed from mutual masturbation to having her penetrate me. It start one evening as we were kissing and fondling each other. Fia was more aggressive than usual, biting my neck, squeezing my cock and balls. Her free hand reaching behind me, pressing against my hole through my panties. I reached around to pull them down enough so Fia could massage my hole, gently pushing her finger inside me. She whispered in my year, "Pauline, I'd love to fuck you."

This made me weak at the knees. Breathlessly I agreed and Fia left me to find some lube. Returning, Fia turned me around to face the wall and penetrated me with her well lubed finger. At the same time, she was reaching around and pulling on my now throbbing erection. I finally begged Fia to penetrate me with her cock, to make me her cum slut.

I could feel Fia's cock pressing against my now well lubed anus. Kissing my neck and shoulders, she began to press herself inside me. I gasped as the head of her lovely cock passed through my sphincter, feeling her sliding inside me. "Cum inside me, Fia. I need to feel you fill me up," I gasped. Fia continued to push in and out of me as she played with my cock and nipples, all the time kissing and nibbling my neck and shoulders.

"Damn, you are tight, Pauline. I don't think I can last very long."

With that, I began pushing against Fia's cock which was now moving more quickly, her hips slapping against me as she fucked me deep and hard. With a final massive thrust and a loud groan, Fia blew inside my tight arse. I could feel her relax against me as she began to soften and slowly slide out of me. Turning around, I kissed her deeply and whispered in her ear, "Thank you Fia, thank you so very much." She then fell to her knees and sucked me until I blew a massive load into her hungry mouth.

While I had been anally fucked before, this time with Fia was the most enjoyable I'd experienced until then and was the beginning of many more exciting episodes.

During the time Fia and I were having our affair, I had changed jobs and was now in position where I had two days off per month. This gave me the opportunity to dress at home and, to that end, I hid a selection of lingerie and other things in my home workshop, a place my wife very rarely entered.

On my days off, I would normally wait for my wife, Jan, to leave for work then shower, and dress in lingerie. If it was a day that I was to visit with Fia, I would put normal street clothes on over my lingerie and drive to her shed. If it was to be a day at home, I would don a dress or skirt and blouse and pretend to be a woman for the day, but a woman who loved playing with her stiff cock.

One day, on returning from work, Jan was waiting for me with a pair of panties in her hand. To my shock, they were black and obviously too big for her. "I found these in the laundry hamper, care to explain?" She demanded.

So, here I was, my wife has discovered a pair of panties that are obviously not hers but doesn't seem all that angry. "OK," I said, "they belong to me. To be honest with you, I love wearing lingerie."

At this I expected Jan to order me out of the house. Instead she just asked how long it had been going on and if I had more lingerie. I told here that I had quite a collection and had been dressing for some years now. "Bring your things in here, I want to see them," she said. Obediently I went to my workshop and collected my things.

Returning to the bedroom, I was shocked to see Jan dressed in a white satin bustier, stockings and sheer thong panties, her dark bush obvious through the translucent material. "Get dressed," she demanded.

Selecting matching bra and panties, garter belt and sheer black stockings, I quickly stripped off my street clothes and began sliding the stockings up my legs, securing the garter belt and sliding my panties over my semi-erect penis. As I began putting on my bra, I looked over to see my darling wife rubbing herself through her own panties, a dark spot beginning to show in the crotch. My cock was now fully engorged and a dark spot of my own was beginning to form on the front of my panties.

"You look surprisingly good," she said as she walked towards me. "But you really need to do something about all that body hair. Tomorrow we will shave you, but tonight we will pretend to be lesbians."

With that, Jan kissed me and directed me to the bed, pulling me down next to her. Kissing me deeply, Jan began to rub my hard cock with her pantie-clad crotch. Then, forcing me onto my back, she straddled me and forced her pussy against my face. Even through the fabric it was obvious he clitoris was engorged, something that I'd only experienced with her on a very few occasions. Her moans were an indication that she was enjoying the experience as she ground herself against my face until she orgasmed violently and loudly.

Removing her own panties, Jan moved around so her sweet arse was facing me and she pulled down the front of my panties so she could access my now rigid penis. Taking me in her mouth, she again pushed herself against my mouth but this time I had free access to her tasty pussy. Reaching around, Jan began to press a finger against my hole causing me to release a pleasured moan. "You like that, do you? Would you like a hard cock inside you?"

"Y-yes please," I stuttered as she slid my panties aside and began pressing her finger against my arse-hole. Pausing momentarily to get a bottle of lube to ease the passage of her fingers. Returning to me, Jan lubed up my hole and her fingers, then began fingering me in time with the movement of her mouth on my erection.

Knowing me well, Jan was aware of when I was about to cum and ceased her ministrations before I did. She rolled off me and reached into her bedside draw to retrieve one of her dildos, the realistic, moderately soft one that I had often admired watching her fuck herself with. Lying on her back, she held the dildo between her legs and instructed me to suck it as if it was a real cock. Not requiring any further encouragement, I took the dildo in my mouth and sucked it deep inside my mouth. Jan placed her hand on the back of my head and telling me that I was doing a good job and that I was a good little girl. This, of course, encouraged me to redouble my efforts in sucking Jan's dildo.

After some minutes of this, Jan pulled me to her and held me tightly. "Did you like sucking my dildo?" She asked.

"Yes, I did, very much," I replied.

"Would you like me to fuck you with it?"

"I've not had anything that big inside me," I accidentally let slip. Oh well, it was out now, couldn't take it back.

"Um, what do you mean, you've not had anything that big inside you?" She asked, sitting up and staring at me.

"OK, I guess I've got to confess. Nothing left for me to do," I replied. I've been dressing with Mick for some time now and, yes, he has fucked me."

"Do you enjoy it?"

"Yes, I do. Very much." Fortunately for me, Jan had engaged in several short affairs in the past and knew I was aware of them. This, I hoped, would lessen any anger she may have.

"Do you love him?" She asked.

"I think I'm in love with him, but I don't love him," I replied. "I'm in love with and love you, but I don't love him."

"I can live with that," Jan replied and proceeded to mount me and ride me until we both orgasmed.

The next morning being a Saturday, we lay in bed holding each other and discussing how we should proceed with our new situation. "I'm going to want you to be dressed as much as possible, Paul. But first we will need to get rid of all that nasty body hair you have," said Jan.

"OK. But, if you don't mind I'd prefer if you called me Pauline when I'm dressed."

"OK, Pauline, so it will be. But now, breakfast."

We got out of bed Jan insisted I wear a dress. "We'll get you some nice night-wear soon, Pauline."

Following a light breakfast, Jan led me into the bathroom, removed my clothes and began lathering me in preparation of a complete shaving. Following this, Jan instructed me to shower and then join her in the bedroom. Upon entering the bedroom, I saw she had laid out my green lingerie set, a very short black skirt and white blouse. The feeling of the lingerie on my freshly shaved body was almost as exciting as the first time I dressed. Jan observed my excitement and gave me a cheeky grin.

"You know, Pauline, I think I'm going to enjoy this new you."