Shopping with Lynn

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"Oh, girl, you're doing great" I told her as I held the top of her head with my left hand and reached under her head and held her throat right above her Adam's apple with my right. I started to fuck her mouth gently as she took my cock deeper and deeper with each of my gentle thrusts. We became as one working towards one goal--getting me to cum. My thrusts became harder and harder as she tried to take my all of six inches down to the root. Most times she succeeded.

She let go of the base of my cock and brought her hand around back to my puckered hole. She probed it gently, circling it and even inserted it as she stimulated me towards orgasm. With that, I grabbed her head with both hands and fucked her face hard. I just couldn't take it any longer. I thrust deep into her throat and held it there for a few seconds until she started to gag, and backed off, remembering what I had told her. But I wasn't going to last long, and Lynn knew it.

I fucked her face hard and with all I had. I could feel my orgasm building as she used both hands to pull me into her, her hands on my hips. With one guttural growl, I began to spew cum into her mouth and down her throat. She took three good shots of my seed into her mouth, not letting a single drop ooze out of her mouth. "Mmmmmm" she mumbled around my cock. She looked up at me and smiled lovingly and proudly.

I raised her up off her knees and kissed her. She shared the semen in her mouth with me as we both enjoyed licking each other's tongues. The mascara that the makeup artist Madeliene had applied back at the store had started to run, and the lipstick was a bit smeared around her lips, but I thought she was beautiful. I took her face into my hands and kissed her face all over. "Oh my god Lynn, that was the best!" I told her. She smiled back at me, her eyes beaming.

"It's just what a girl does for her man."

"And now, perhaps you'd like to see what a man does to his gurl?"

"Oh, please Jim, you know I do."

"Well, then, let's just sit here on the couch in front of the fire," I said, "as someone here is way overdressed."

We started kissing again, still tasting my seed in her mouth. "Lucky her," I thought, knowing she'd be tasting me the rest of the day, as I was soon to taste the same of her. The zippers on the cups of her bustier were still open, so I started fingering her nipples again, reaching into the cups and teasing them. I handed her my fingers, as I ordered "Lick," and she complied, and then I went back to teasing the nipple. I moved down, away from her face to kneel in front of her, and widened the slit in the cup, and tongued the nipple through the undergarment as she moaned.

I unzipped the center zipper of the bustier and spread it open, exposing her bare breasts and hardened nipples, and seized them with both hands, lightly pinching then rubbing them. Her areolae were a dark pinkish-brown, hairless because she had shaved them earlier in the day. I leaned in and started licking them, teasing them. Like me, the nerves in her nipples went straight down to her nether region. I'm sure her clit was now getting very uncomfortable, locked up in chastity. Chastity that she herself had inflicted.

As I continued my suckling on her breasts, I reached down and pulled her panties down. Jennifer had told her the panties go on over the garter, or in this case bustier, straps holding the hosiery up in place, and Lynn knew that already anyways. She lifted her cute little bottom up off the sofa as I pulled them down and off. My god she was beautiful, the bustier opened up, breasts free, clit engorged and turning red.

"The key, Lynn, where is the key?" I asked her. "In my jeans pocket," she told me. "Hurry, please."

I looked around for the bag I had brought them home in and spotted it on the floor near us. I pulled out the jeans and, never missing an opportunity to gently tease her, held the jeans up to my face and very obviously and playfully started to sniff them. "Nooooooo!" she cried. I reached into the right-hand pocket of the jeans and pulled out the key on its gold chain. "Is this it?" I innocently asked. "Very funny, Jim" I got in return, "Now please get this off me," pushing her hips out to me, offering her sex.

I unlocked the lock of the chastity device and slid off the tube encasing the clit now turning cock. I gently held her ball sack and carefully removed the clear plastic housing that had encircled them. With each beat of her heart, she was getting harder. I could see it pulsing upward and becoming more erect. I immediately went down on it and took her to the root. Still gently holding her balls, I sucked at her now-hard cock, taking her into my throat, backing off to lick the head, then sucking it back down. I was loving it, the intimacy, as she was. I looked up into her eyes as I slid my hand that had been cupping her balls down past her perinium to her rosebud and started playing with it, pushing a finger in. "Ohhhhh," she moaned. I had taken her before, and had even rimmed her, so I knew how sensitive her pussy was.

I knew she was close as she started leaking. I could just taste the first drops of her pre-cum in my mouth. I knew her flavor, and she knew that I loved it. She knew I loved doing this to her, for her as I redoubled my cock-sucking efforts. My favorite technique is to throat it, back off and circle my tongue around the head, then take it back down. She loved it too. Throat, circle head, repeat, throat, circle head, repeat. That and my finger wiggling around inside her pussy sent her over the top. I felt the warm semen hit the back of my throat and tasted it a split second later, and when I did I took the cock deep in my throat and let her thrust. I held it there as long as I could, then eased off to enjoy the almost flavorless thickness of her jism.

"Mmmmmm," I moaned around her cock.

"Oh, my... oh my god" was all she could say.

I slowly sucked her back down, repeating the motions I had brought her off with but slower and even more lovingly, letting her enjoy the moment as her cock softened inside my mouth, changing back again to a clit. I eased my finger out of her pussy, feeling it tightly close behind the withdrawal.

"That was so good Lynn. You taste so good. Oh, and I hope you have a happy birthday!"

She smiled at me, which was all I needed to see.

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5 Comments
StrappySandalsStrappySandalsover 2 years ago

Yes, nicely written! You capture the emotional uncertainty very well, and even manage to make this old-school boomer consider something different! Thank you!

JiminNCJiminNCover 2 years agoAuthor

Anonymous- try SilverDaddies.com and begin to chat. There are people like us there. Maybe you'll get lucky too, like Lynn and I!

AnonymousAnonymousover 2 years ago

I wish I could find any friends.

AnonymousAnonymousover 2 years ago

Thank you for capturing the feelings we cross-dressers often have, especially as we are just beginning our journey. I like how she’s not portrayed as a sex-fiend, but as a sensitive, not-quite-sure of herself young woman. Well done!

AnonymousAnonymousover 2 years ago

This is a very good series! I wish I could find such a special friend!

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