Sissy's New Toy Ch. 01

I lay back on the bed next to Cindy, totally relaxed. The room was hot from our exertions so we lay without touching. At least until she began to run her fingers over my groin, finding where my panties were soaked through with my cum.

She moved to lay on her side, propped on her elbow, her left breast laying heavily against my arm as her right hand traced the edges of my panties and brushed my shaved legs. I shuddered happily as one finger slid down to stroke the gusset of my panties, a suggestive move toward my erogenous bottom.

I closed my eyes as her hand moved up my body, dancing over my cock for a few moments, ensuring that it recovered to half-hard. She went further up, over my smooth abdomen toward my bra and the soft, full fake breasts that filled the satin, lace, and wire completely.

I looked and saw her cupping my breasts, her fingers touching and swirling the prominent nipples around where they announced themselves in the otherwise smooth, pink satin of the cups.

The journey completed by touching my face and my lips. Traces of lipstick still rubbed off on her fingertips.

"You are a divine creature, Janie," she said at last, satisfied with her inspection.

"Thank you, honey," I said with a smile. I was in a glow of sexual satisfaction and acceptance. If you'd asked me three months ago, I'd say such a woman as Tessa didn't exist, could never embrace my passion for the feminine and find her own pleasures in it. Needless to say, I'd do anything for her.

Her hand had returned to my panties, stroking them and bringing my cock back to life for round two.

"I think I'm ready for the next step, Janie," she said after a couple minutes of silent stroking.

"Anything, my goddess," I breathed, the flow of erotic pleasures in my cock was beginning its journey around my body and mind.

"When we play, I tease you about being a slut and a panty-loving sissy..."

"And more," I grinned.

"Exactly. I think the theme is pretty clear, but we're missing the main event." She paused again, still stroking, though I was beginning to realize that this was very serious to her.

"What do you mean?"

"I think it's time you became a cocksucker."

While my face flushed and I suddenly found swallowing to be difficult, she continued to hold my cock. She felt it swell in her fingers. I couldn't reply but she was smiling.

"Are you ready to play?" That was our code phrase for sexual play time where I would get to dress all sissy and we'd experiment.

"Yes..." I said quietly.

She leaned back to reach underneath the pillows on her side of the bed. I got a lovely view of her tight body and healthy D-cup breasts. I was more blessed than any man or any sissy had a right to be.

When she leaned back, she had a rubber cock in her hand. Without thinking, I let out an exhale of tension.

She raised an eyebrow. "What did you think I meant? No, don't answer. I think I get the message. Anyway, this is my cock. It took some time to find the right one since I wanted a beautiful one that was also big enough to satisfy my girlfriend, Janie. Do you like my cock?"

"Yes, Tessa, your cock is beautiful and sexy."

"Thank you. I'm very proud of my cock." She got up until she was standing on the bed over me. I watched her carefully step into the strap-on harness, pull it up her legs, and adjust it for a few moments until he stayed in place and was positioned just right.

"Mmmmm, yes, I like my big, heavy cock," she purred, swinging it around with just a movement of her hips. "I like to touch my cock too." She traced her fingers up and down the shaft before slipping it into her grip and beginning to stroke it.

"Oooo, yea, that feels good. I like to stroke my cock. Makes it so hard, especially when I'm looking at my girlfriend."

My panties were tented with my raging hard-on and it was hard to keep from reaching down to rub myself through the cum-soaked satin.

Tessa got back down on the bed, laying back propped up with the pillows.

"Janie, will you kiss my cock?" Her hand was still moving in a motion similar to a guy masturbating but just off enough that you could always tell she was a girl.

I slid down the bed and then got up on my knees next to her hips.

"Just kiss it, that's all, honey," she teased. I looked at the dildo more closely. The color was a surprising match for Tessa's skin tone and the detail of the mold was impressive with a distinctive cum-hole and circumsized foreskin. It was then that I noticed the foreskin was moving up and down with her hand. Fascinated, I moved in for a closer look.

The detail was really amazing. If I were to squint, I could easily mistake it for a real cock. I felt her hand touch my head, not pushing but almost suggesting that I kiss it. So I did. The 'skin' of the head was soft with a hard core. It must have cost her a fortune.

"Ooo, baby, that feels so good. Kiss it all over."

I got myself settled so I could lean down to the whole cock easily and began to kiss and lick the whole thing, from the fat head down to the hairless but moveable balls. I saw little traces of the slutty red lipstick I'd chosen for the evening.

"Janie, will you suck the head? Just the head a little, honey?" she whined playing her role perfectly. And if I wasn't mistaken, I could tell that her sex was enjoying it too.

I placed my lips around the head and gently drew it into my mouth. I shuddered at the sensation. It was something I'd fantasized about now and then but never felt like I really wanted to bring it up to Tessa. Maybe after everything we'd done together I was still afraid that I could push her too far.

But I quickly forgot about all this and entered that zone where I'm completely focused on her and myself and the sensations... the weight of my breasts in my bra pulling the straps against my skin... the way my panties slide over my bottom as I shift my cock in the front... the enforced position of my feet strapped into 4" high heels. Now I could add the sensation of taking a soft cock into my mouth.

The rubber felt cool at first, but as I worked it, it warmed up and made the illusion seem even a little more real. Tessa didn't have to play at asking me any more. I easily moved on from sucking the head to sliding more of it in my mouth. I used lots of saliva, getting it nice and slick.

"Oh yeah, fuck that feels good," she moaned as I began to bob my head up and down on the cock, keeping my teeth from the edges but pressing my tongue against it all the way up and down. I was about halfway down, I guess, when it would hit the back of my throat. Those were the moments where she gasped a little.

The way the foreskin shifted under my lips was amazing and it didn't take much for me to dream that it was a real cock I was mouth-fucking. She gasped again.

Of course! She was getting rubbed by the base of the dildo. As soon as I caught on to that, I changed my blowjob technique to stimulate her more.

She was watching me intently, sucking 'her' cock, and I saw her face and breasts flush as they do sometimes when she gets very aroused. I wanted to reward her for bringing this into our play time so I got a finger nice and slick with my saliva and went to press against her asshole.

Her eyes shut and her hands went to pulling on her thick nipples. She was past words as I slowly felt her ass open and let my finger slip inside. She began to buck up, thrusting the cock into my mouth and grinding the base against her clit. I let her work it as I slowly started fucking her ass with my finger.

After only a couple minutes, she came, her ass clenching down on my finger and her hand reaching out to my hair to hold my head as she ground against the base, getting the real peak out of the orgasm.

Soon, we were back to laying on the bed. She was breathing hard, her eager cock jutting proudly over her pussy. Her fingers reached over and found my aching cock in my wet panties.

"My cock does something else too," she whispered grinning.