A Gentleman for Lynn Ch. 03

We laid there on the bed side by side still in the sixty-nine, just enjoying licking the last drops of seed dripping from our cocks. I was completely spent I knew, but I suspected she still had more to give.

Her head was nearest the headboard of the bed and the nightstands as mine was at the foot of the bed. "Lynn, in the right-hand nightstand is some lube, would you get it?" I asked of her.

"Jim, I told you I wasn't ready yet for that" she replied.

"I know that darling," I told her, "And I totally respect that, but trust me, you'll see."

"Okay then, and you know I do" she smiled at me and reached into the drawer for the lube and handed it to me.

"In about ten minutes you're going to be begging me" I reassured her as I simply set the lube next to her on the bed sheet. "Now, get up on your knees with your head on the pillow."

"Jim, I really don't want to be penetrated, I'm not ready."

"Who said anything about fucking?" I knew she didn't yet understand what I wanted to do next, but she did what I asked, trusting me. On her knees and with her head on the pillow, her most intimate and sensitive body part was now open for my lusting eyes, and more importantly my tongue, as I leaned in to pleasure her again.

"Oh my god" she said as my tongue started circling her puckered rosebud. "That's unbelievable." She was hairless there, the darkened anal area having been shaved clean, along with her ball sac, earlier in her shower at home when she was getting ready to come over, and before she had fastened the chastity fixture. I saw the red welts on her perineum where it had dug in while keeping her clit in place all afternoon. I licked and kissed the welts, trying to heal them.

I started rimming her with all my being. Circling the anal orifice, licking up and down her crack from the base of her spine to her nut sac, licking from cheek to cheek right over her hole. I knew she was in heaven. I could tell by the reaction of her cock, which was hardening by the second. "Now, squirt some lube on my hand, Lynn" I asked her as I held out the lube to her and opened flat my left-hand palm. Now she understood! She squirted a generous glob of the heat-generating lube into my hand and dropped the bottle on the bed beside her, closing her eyes and going back to enjoying my efforts.

I rubbed the lube all over her now-turgid cock and ball sac as I kept rimming and began to massage the cock as I licked her ass. "Oh, yes. Don't stop" she cried out. I had no intention of stopping until she spewed again, of course.

I masturbated her with my left hand as I rimmed her, occasionally penetrating her anal cavity with a hard straightened tongue, technically going back on my assurance of not penetrating her, but she didn't seem to be complaining. Rather, she was moaning into the pillow, clearly loving the attention I was giving her most sensitive and private area.

The dual stimuli of rimming while masturbating her did not last long. Her cock began to spurt the rest of whatever seed she had left into my hand and onto the bed. I kept masturbating her and moaned approvingly into her asshole. As I slowed my hand's pumping, I slowed my licking also to ease her down, not wanting to over-stimulate her during those first moments right after orgasm. When she had finished cumming, she collapsed onto the bed and I laid down beside her, my arm around her. "Mmmmmmm, that was great" I said.

"Great for you? I've never...Oh my god thank you for that. I never thought I could cum so hard, and on a second time. I'm just so warm and happy right now."

We laid there for quite a while, enjoying the rest of the afternoon into the early evening together in bed, the post-sexual endorphins causing us both to nod off into a nap together, her garter still around her hips and my arm around her shoulders.

She stirred me awake by rubbing her bum into my cock. "Jim," she said.

"Mmmmm, hello there."

"I'm ready."

"Ready for what?" I asked her, and was hoping the grinding of her bum meant what I thought it meant.

"To take you inside me," she replied, "as a woman takes a man inside her. I want you to be my first."

"Are you ready to be placed back into chastity, Lynn?" I asked her. I knew that her deepest fantasy was to cum hands-free, wearing the chastity device, while getting pounded from behind.

"Yes. I want this so bad," she replied. She handed me the device and asked me to fit it back on her cock-now-clit. I was beginning to understand her... the chastity device, once in place, kept her member small, like a clitoris. After all, what girl wants a 5" long clitoris?

I fixed it in place and re-locked it. She adjusted her ball sac to remove the pinching between it and the hard plastic ring now encircling it. I asked her for the lube and she handed it to me. "Can you get up on your knees again, Lynn?" I asked her. She willingly complied. "Would you like to put your bra back on too?" She nodded, knowing that she and I both understood what she needed at this moment, as lovers do.

She knelt up on the bed and I placed her brassiere over her arms and shoulders and she looked down and fixed the clasp in the front of the bra. She looked over her shoulders and we kissed.

My cock was stirring in anticipation of what was to come. I broke the kiss, and had her lie face down, bum up in the air, legs spread apart, allowing me the access to her tender, private hole still moist from before. I squirted a generous amount of the warming gel onto my fingers and began to finger her pussy, just with my middle finger slowly going into the hole past the first outer sphincter, and then to the second sphincter about an inch inside. "All Okay?" I asked her, and she smiled back at me. "Ready for a second?" She nodded with her eyes closed, clearly enjoying the intimacy we were experiencing.

I took my index finger and added it to the middle finger, continuing to probe and wiggle them slowly side-to-side, and in-and-out of her hairless, puckered anus. When she was easily able to take my fingers all the way, I knew she was ready. I took the lube and squirted some onto my manhood which was now more than hard enough to make the journey now demanded of it.

I repositioned fully behind her, surveying the view in front of me. An eager woman, her narrow girlish hips still wearing the black garter and once again the lilac-colored bra she had worn to the hotel. I placed the cockhead against her opening and gave a slight push. The cock met with resistance, her virgin pussy preventing it from accessing what she herself wanted to offer.

"Lynn, just push out slowly." I told her. "I want to," she replied, "But it's hard."

"That's okay, you're doing fine," I said, "Take your time. You know you want this."

I pressed the cock against her hole a little harder as the lube worked. The head of my cock entered her. "Slowly now, Lynn. You're controlling this now, not me. Take your time."

"This is so different than anything else I've ever felt," she told me as she took more and more of me slowly into her pussy. I could feel the undulations of her anal canal around my cock, the two sphincter muscle rings clamping down around it. It was divine. She was divine. She was becoming a woman.

Finally, she had pushed herself all the way down my shaft. "Okay, now you can start, but go slowly first." I took her pelvic bones in each hand and slowly began to fuck her, hearing her moan with each slow inward movement.

Soon, we were truly fucking. I knew enough not to just thrust in and out, but to seek out her prostate with my cockhead. We had talked before about this moment and how she wanted to cum through the chastity device, hands free.

We were in unison, me thrusting forward into her, pulling her pelvis towards me and her willingly taking it. "It's beginning," she said. "I'm leaking." I was rapidly building up past the point of no return. It was, after all, my first time too, and after years of anticipating this first time, looking down at the view of her bra, garter, her narrow hips pushing back against me was soon too much to control and I started jetting into her. I could feel my seed entering her as she could feel hers dripping past the slit of the chastity device onto the bed below her. "Oh, god I'm leaking bad." I was thrusting hard into her, against the prostate, forcing seminal fluid down and out her clitoral hole while my own seed was mixing with the lube making her pussy, her anal cavity, even more slick.

With one last thrust I stayed deep inside her, as deep as I could, and reached around and felt the last rope of her cum dripping past the slit of the CB6000. I took it on my fingers and brought it up to my lips, licked them clean, and reached down and kissed her with it still on my lips and tongue. "We've done it!" I thought to myself as I laid down on top of her, cock still in her ass, but getting softer and being slowly pushed out by her sphincter muscles.

"My god, Lynn." I whispered into her ear. "That was unbelievable!"

"Mmmmm, I'm a woman now, aren't I?" she softly spoke.

"Yes, you are, and no one can take that first experience away from you. You'll remember it as much as your first girl back in college."

We laid there a bit more, enjoying the true post-coital intimacy with each other.

I was first to spoil it. "We need to get you cleaned up, you know." She frowned and said, "I know."

She undressed, taking off her bra and garter, and went off to the bathroom and took a quick shower. While she was in there, I laid out her bra, panties and the camisole I had given her earlier along with her street clothes.

She came out of the bathroom still in chastity. I handed her the gold chain and she placed it around her neck, and then she dressed, first the bra and panties, then the camisole. We put the corset, garter and hose into the box the camisole came in, and into the shopping bag I had gotten from the store. Finally, she put her boy clothes back on.

"Thank you so much for this afternoon, Jim" she said looking up at me.

"Trust me, I enjoyed it as much as you" I replied. "I'm already missing you."

"I know, me too!"

"But, I'll be back out for your birthday, right?" I asked her.

"Can you?" she beamed back at me. "Would you?"