Night School Ch. 02

Night School, Chapter 02

*****************

Sorry for the long delay; I hope you enjoy the continuation of Cindy and Jerry's encounter

*****************

Cindy and I were cuddling on the sofa; both spent from our orgasms. We held each other as we calmed down from the excitement.

"Would you like that coffee now?" Cindy asked me, her head resting on my chest. I said I would but didn't want her to move. Eventually we had to move, "I'm not running away" she uttered, slowly pulled herself to standing. I looked at the body before me as she held out her hand for me to get up as well. "Come help me." I stared at the juxtaposition of what I was seeing. Her face, lovely, smooth and very feminine. Her shoulders were soft, and her chest bore the breasts of a young woman, firm and supple. Her legs were long and luscious; and except for the long dark brown hair of her head and thin eyebrows, she had no hair on her body at all. The only thing that stood out on this beautiful older woman was the semi-hard cock and the balls that dangled between her legs. My inspection of her body didn't go unnoticed. My eyes, returning to her face were met with a stare and a smile. "Well, what do you think?"

"I love it, every bit of it." I replied in all honesty.

Wearing only our panties, our cock and balls hanging out of the leg openings, we walked into the kitchen where the brewed coffee was waiting in the pot. We grabbed some and sat at the round kitchen table, holding hands as we sipped our coffee. "You're married." She said to me, a note of concern in her voice and a look of despair on her face.

Seeing her state I said, "Well, first off, it's not going to be as bad as you are likely imagining right now." Her look changed to that of confusion. "My wife is fully aware of my bisexual side, and very aware that I have, well had, a boyfriend. She is fully supportive of me indulging this side of me. I'm not sure how she would have felt if you were a genetic woman, that would have been a conversation. We have had many conversations about such things from both perspectives; and our mutual understanding and support remains strong between us. She will not see you as a threat. In fact, I'm almost positive she would accept you not only as my lover, but as a friend of the family."

"That is incredible", she began, "my wife left me when I came out to her as liking women's clothes. She didn't stick around long enough to even try to understand me, or my desire to not only wear women's clothes, but transition into a woman as well. I've been on my own for the past three years."

"Have you had any relationships since then?" She bowed her head and shook it with a soft "no" escaping her lips.

"I tried meeting people, but the few guys I met didn't stick around when they learned that I was packing. Sure, I have a couple close friends, but they are women. They helped me through my transition and took me shopping to build a new wardrobe. I work with them in a small real estate office. The owner is a guy, but he is very supportive of me and even gave me the time off when I had my surgery". It was clear to me that Cindy had gone through it. I asked about the class and what drove her to try it. "Janice and Rose, said I might meet someone at the class, and if nothing else it would help me fill my evenings with something other than work. I love movies and they thought it would be a good fit. I agreed and enrolled."

She looked at me, eyes shimmering, almost to tears. "I never expected that I would meet you. I really don't know what it was, but as I said before, I knew the instant you walked into the room, and I was screaming in my head for you to come sit beside me." She squeezed my hand.

I replied, "I'm not sure what it was either, but as I scanned the room and saw you looking back at me, I felt what I can only describe as a connection. I kind of knew I was going to like you and hit it off."

"I was overjoyed when you sat next to me, and I so wanted you to know sooner than later who and what I was, but I was so afraid to mention anything in the classroom in case you rejected me. I don't think I could take that. But, when you let me touch your leg, and even cuddle against you, I just knew it was all going to be okay."

"I'll be honest, I was surprised when I felt your hand on my leg, but I wasn't going to push you away. When the lights went out and you cuddled into me, I felt a warmth inside that I had only felt with my current wife."

"Still, I was worried. That's why I asked you to come over tonight. I just had to know if we could have something between us or not. I hadn't even checked to see if you were wearing a ring in the class, and when I saw it as you walked into the house, I almost fainted. But, as they say, in for a penny in for a pound, I kissed you. And here we are."

"And here we are." I repeated her words, giving her hand a squeeze of my own. I leaned in and we kissed. My other hand drifted down to her leg and slid up her thigh, until it met her now hardening cock. I wrapped my fingers around her shaft and felt her moan into my mouth. I slowly rubbed her shaft under the table, knowing I not only wanted more at that moment, but I wanted more from her for a long time to come.

Our kiss broke; her arms now wrapped around my neck holding my head close to hers; and my hand still holding her cock. I said to her, "Have you been fucked before?"

"No, Jerry, but I'm hoping that you want to be my first." She said, her face so close to mine I felt the breath of her words on my cheek. I smiled and replied, "I want that too." Cindy and I kissed once more.

Taking my hand, she led me to the stairs, and I followed her to her bedroom. It wasn't a surprise to see the room decorated in pink and pastel accents. Cindy had fully embraced her femininity, I noticed it downstairs as well, but not as much as in her bedroom. She excused herself, and I heard the shower running in the master bathroom. It wasn't much longer than a few minutes when she returned wearing a white silky see-through nightgown, her panties replaced with a pink thong. I took her into my arms, and we kissed long and slow, just as we had at her doorway an hour or so earlier. I pushed her onto the bed. She shuffled into a position and leaned over to her nightstand where she quickly withdrew a condom and tube of lubricant.

She handed me the lube as she opened the condom wrapper and slid the sheath over my cock. I put some lube on my fingers, rubbing it to warm it up. Reaching between her legs, past her hard cock, sliding the thin strip of her thong to the side, I found her hole and rubbed the lube around the opening. Adding more to my fingers, and warming it again, I probed at the hole and slid a finger inside. She moaned at my touch. I continued to apply the lubricant to her hole before climbing up on the bed between her legs. She lay there looking at me with a huge smile on her face. "Fuck me Jerry, please fuck me." She lifted and spread her legs as I scooched up between them. My cock, covered in the thin condom, found its way to her well lubricated hole. She gasped at the first touch and said, "please". I inched forward and slowly began to push the head of my hard cock against her opening. It took a few moments, but I felt her muscle release allowing me entrance into her. I went slowly, relishing in the tightness of her ass on my cock, and not wanting to hurt her. I soon made my way deep inside of her and held myself there as she adjusted to my girth. Then, equally as slowly, I pulled out almost all the way leaving the tip inside past her tight ring. I reached for the lube and squirted more onto my hand, rubbing it over the condom covered cock and against her hole. Pushing once more, I slid back into her. She wasn't in as much discomfort this time. Still going slowly, I repeated the lubrication once more before beginning a slow but regular flow in and out of her. We were fucking and loving it.

I balanced myself on her legs as she held them, the fingers of our hands touching each other as I moved inside her. I slipped one hand free and took hold of her cock, urging it from its thong-prison. I was slightly imbalanced by that and had to adjust my position to keep fucking her, but I wanted to play with her cock at the same time, so I made it work. The moan she let out as I gripped her firm member let me know that she appreciated the extra attention. Her cock slid nicely through my fingers as I rubbed it, the remnants of lubricant still on my fingers. It wasn't long before I was ready to cum once more, and I could tell from her movements and moaning, that she too was in a similar state. I began rubbing her cock faster and was soon rewarded with her cum splashing over my and on to my belly. I sped up my fucking, and with both hands holding her legs once more, I focused my thrusting and then slid in as far as I could go, holding myself in place as I filled the condom with hot cum. She felt me cumming and screamed her pleasure.

I pulled out slowly as I lowered her legs and then rested on top of her. We kissed, our bodies writhing together as we found a comfortable position on her bed side by side, in each other's arms. We cuddled for a while before she said, "We should clean up." She led me to her shower. It wasn't huge, but we managed.

"Will you tell your wife?" she asked hesitatingly at the door, a worrisome expression on her face. We were dressed, me in the clothes I wore over there, and her in a pair of yoga shorts and a thin T-shirt top, tight enough for her nipples to form small tents in the fabric.

"Yes, we have no secrets." Her expression was saddened. I continued, "This is not the end of us. In fact, I want you to come over tomorrow night for dinner, we can watch the DVD, and you can meet my wife. Trust me, she is going to absolutely love you." We hugged and kissed.

Barely twenty hours later, Cindy knocked on our door. From the kitchen I heard Kelly heading to answer it. I heard the door close but nothing more. Walking to the hall I saw Cindy's face, poking over Kelly's shoulder as the pair embraced in a huge hug. She was happily crying.

************

Up next: Time to do our homework