This is not the story of our meeting or early interactions, that's seperate.
The holidays were coming up, and we all had our plans and thoughts of gift buying in our heads. It was nearly last-minute but I had an idea, so I texted Adrienne and told her what I had in mind. She liked the idea enough to give it a shot so we picked a day, a time, and it just happened to be yesterday so this is all fairly fresh.
We had been texting constantly the days leading up to yesterday, going back and forth deciding which toy I was going to buy her and watch her use. She finally decided on a medium size vibrator that she could use in both her holes to loosen up for the "huge" dildo she already had. I told her I'd give her the money and she could go in and buy it alone, yes I was nervous. So we met at the sex store she picked, decent enough looking place I suppose, although it was a 45 minute drive for me. I parked beside her and hopped into the passenger seat of her Bronco, we made small talk for about 5 minutes before she slid across the bench seat towards me. She started rubbing her hand on my crotch as she told me the idea she came up with on the drive over. The basic idea was the same, but she wanted me to go in with her and look at the toys, but if I went in with her and didn't rush her she'd blow me and let me cum on her tits in the parking lot. By now I was experiencing a distinct lack of blood flow to my larger head, so I agreed. She unzipped my pants, worked my hard cock out, and paused, I asked what was wrong and she said I was bigger than any other white guy she'd been with. After a couple pumps she gave it a quick lick and then opened wide and took about a third of it in her mouth before the head hit the back of her throat. She took her mouth off, spit in her hand, and then bobbed up and down for a few minutes, working her tongue, mouth, and hand together. She must have felt my balls tightening because she pulled away, slapped the head of my cock and told me to make myself decent and that she'd finish if I held up my end.
It was early on a Wednesday afternoon so it was just us, the clerk, and shelves full of toys in the store. I was surprised by both the store and the clerk, both looked a lot better than I expected. There were a few shelves of porn up front, but most of the store was dedicated to fetish playthings. The clerk was a tall, large, older white woman with an attractive face, black hair and humongous tits. She gave us a warm smile and welcome as we came in and the typical offer to help. I was starting to loosen up as we walked around looking at vibrating eggs and rings, penis extensions and nipple clamps. I remembered not to rush Adrienne, and continued to reply to her comments on the different toys. We worked our way around until we were near the desk without Adrienne being satisfied, it must have showed becaue the clerk offered to help. Adrienne told me to look at the butt plugs while she talked to the clerk, so I stood there trying and failing to hear what Adrienne didn't want me to hear.
They walked, talked, laughed and picked out things I couldn't make out for at least 10 minutes while I stood there pretending to admire the toys in front of me. When they finally came back to where I was standing Adrienne told me to pick a butt plug. I thought she wanted a dildo, but I picked a red, medium sized one remembering how much she liked being stretched. When I tried handing it to Adrienne to add to the bag she had picked up while walking around she told me to hold on to it and follow the clerk. The clerk, she introduced herself as Autume, walked over to a row of dildoes and vibrators that she and Adrienne had been looking at. Adrienne told me to pick one and hold on to it, so I picked a slim blue vibrator, the package said 7". And if I'm not mistaken Adriennes bag looked a little bulkier than the minute before.
I then followed the clerk to the counter where she rang up the vibrator and butt plug, then told me to turn around while she rang up Adriennes bag. When she told me the total I looked at Adrienne to say we needed to put some things back, but the clerk interrupted. She told us she would give us a 75% discount if I would go in the back and do whatever Adrienne said. Adrienne agreed for me as she unzipped my jeans and pulled out my dick, saying she had already gotten me ready and I was ready to cum any minute, so I would listen well. Autume led the way to the back room and Adrienne pulled me by my dick. When we got there Autume closed the door, and Adrienne sternly told me to strip, after a moment I unbuttoned my jeans, pulling them down with my boxers and my hard dick popped out. She slapped my cock and told me not to be stupid, to take the rest off. When I was completely nude she and Autume circled me, eyeing me, sizing me up. They had me bend over, spread my cheeks, stretch my ball sack, and a few other weird things. When they were done, my cock had shrunk from the chill, Autume said she had seen bigger cocks on her young sons before puberty and they both laughed. Then Adrienne kneltdown and started sucking my dick, she kept as much as she could in her mouth as it swelled, my balls started to tighten and my muscles were tensing when she stopped completely. She teased me like that for what seemed like hours, but was probably 15 minutes, keeping me right on the edge of my orgasm. I was almost ready to start begging her to let me cum and it must have shown because she stopped, tightly grabbed my balls and asked if I wanted to cum. I must have said yes 3 or 4 times before she told me to ask nicely. I took a breath and said yes ma’am please, when I did she looked at Autume and said she already had me ready to be her little sissy-boy bitch. When she said that she jerked my cock and balls and I came, I came all over the floor and kept cumming as I dropped to my knees. Adrienne and Autume laughed as Autume said that I was going to make a good little sissy.
I was still on my knees, and they were still laughing as Adrienne handed me a pair of thong panties, and told me to put them on and tuck my lil sissy-cock so it wouldn’t show. When I had done as I was told I was once again ordered to model, and they both agreed that a sissy boy should never have hair around his sissy clit or ass pussy. Adrienne told me to lay on the table and stay still, I did as she said as they tied me to it. She waxed my groin and sack, untied me and bent me over, and waxed my ass. I only kept from screaming because she said if I did she'd dress me up and leave me for the customers to play with.
She then stuck a slim but somewhat long butt plug in my mouth and told me to suck as I put my panties back on. As I was sucking on it, thankful it wasn’t the one I had mistakenly picked, she asked Autume if there were any good movies showing. A sense of dread struck me as Autume said the theater in the strip mall nearby was showing a new animated movie, Adrienne said that would do as she pulled the plug out of my mouth. She told me to move the thong to the side, and slowly but firmly pushed it into my ass. Autume was once again laughing, this time at my expression, I was conflicted, it hurt but feeling so full and stretched felt good. Then Adrienne flicked a switch and it started to vibrate as she ordered me to finish getting dressed. Walking was a whole new sensation, but I made it almost to the door before Autume stopped us and said that little sissy-cocks shouldn’t be seen. Sure enough mine was starting to show despite tucking it into the thong. We once again followed Autume into the back room, I was ordered to strip as Adrienne grabbed a handful of ice cubes from the freezer. The freezing cold shrunk my sissy-cock to a nub. When Adrienne pulled her hand away Autume put my sissy-cock into a leather sleeve that constricted and attached to the butt plug. Then she attached another device around my balls, strapping it to my leg. I didn’t understand until she pulled on a cord and I felt my balls stretch, Adrienne laughed and said she hadn’t even thought of that. I was instructed to dress again, and this time I could tell my sissy-cock would stay tucked. Autume’s parting words invited us to come play with her and her sissy-boy sometime.
We rode to the theater in her car, it was a short drive but sitting down pushed the butt plug close enough to my prostate that I was straining against the sleeve. Adrienne could see my torment and told me if I even so much as touched my sissy-cock without permission I would be punished. When we got there I was very glad it was a matinee show, I just knew I was walking a little funny as we bought tickets and found our seats in the middle of the theater, we were the only people there. When the lights dimmed and the movie started she told me to put my pants around my ankles, as I did she reachd and flipped the switch on my plug again, it must have gone to high speed and I could feel my cock straining against the sleeve but unable to harden or straighten. Halfway through she asked me how my ass felt, if there was any pain, I told her it felt really good and didn't hurt anymore. She smiled and "Good," she said as she pulled out the plug I had picked for her "because this is next when I get back from the bathroom." I waited nervously until she came back and sat down, she told me to lift my butt up and pulled out the plug, unhooked the sleeve and rehooked it to the bigger one on the seat beneath me. She told me that if I got it all the way in and made it through the rest of the movie without a sound or otherwise being bad, she might let me cum. Hearing this I slowly started to sit on the new plug, seeing my face she laughed and said the one I had in me before was made to be easy for virgins, but this was for experienced ass-whores who needed to keep their nicely stretched assholes.
I managed to get it all the way in without a peep, and there I sat, pantsless with my cock between my legs, balls strapped to my leg, and butt plug in my ass. If anyone had seen me they surely would laugh. I sat like that for a while before she glanced over and said that for doing such a good job I deserved a cock sucking, I was elated, finally I could release the pressure that had been building for hours. I was confused when she pulled my head to her chest, but I thought I'd get to suck on her F cup tits, then she undid her pants and pulled out a big plastic cock. I started to jerk back before she pushed my head down on it, telling me to suck it or I'd never get to cum. I still don't know why I was doing any of this but I opened my mouth and let her push my head down. This was my first experience with a cock in my mouth, but I didn't think she would know if I was doing a good job. She let me suck it until the credits rolled when she pulled me back up, tucked it away, and told me to make myself decent. The walk out with the new butt plug was awkward, but felt amazing. When we got in her truck she explained that I was going to follow her, in my truck, back to her place where she would start the rest of my training. She dropped me off beside my truck, and when I was ready lead me to her house.
Once inside she had me strip off all my clothing and wait for her, she brought out a schoolgirl outfit, complete with pantyhose and wig for me to put on. As I pulled on the white lacey boy shorts and padded white lace bra she began to explain I would first pleasure her and then she would teach me how to be a good sissy boy for her. Once I was dressed she had me step into a strapon, it was huge, easily 3 inches bigger than me and a full inch wider. As she strapped it to me she said that this is what a real cock looked like, and soon I would begging for it in my ass.
****I know this is left as a cliff hanger, but it's what I have so far. If you like it please leave a comment letting me know what you like. The same goes if you don't like it.****