All Comments on 'His Teacher, The Transsexual'

Call me! Quick! loved it!

Very sexy.

I wish I could have had a teacher like Ms Sin back in high school! However- since I didn’t - it’s fun to vicariously imagine being Greg, getting tutored and anally domination by a gorgeous and strict Shemale teacher.

I would love to read a continuation of ‘His Teacher, the Transsexual.’

Wow!!! I’m hard and thinking about it!!

is there any story where the tranny gets fucked or is that illegal on this site

Great story, would love to see a follow up, considering the tutoring sessions were highly recommended.

I was hard as hell throughout this entire story, thinking about Ms. Sin and what unfolded into a hands on Health class. If I were a student at this high school, I’d be so excited to take health class.

If I were Greg, I’d be signing up for as many tutoring sessions as possible. So Hot! 🔥🔥🔥

I wish my high school teacher was like Ms Sins!!! I would have eaten all of her cock after she fucked me, though!!

Great story I wish that could happen to me that is one of the biggest fantasy that I have. To be with a shemale and make me suck her cock. R. D.

I would enjoy a sequel please.

While the story is hot, I really wish authors would drop just a modicum of reality into their sex scenes. No way is a 10" dick that is "thick as a baseball bat" going to go into a non-lubricated ass that has never had anything in it before. That would rip and bleed and not be pleasurable for either party. Plus, the dude is not just going to spring back into his clothes and walk away without feeling every bit of that pain...

What is it with these unrealistic 10” dicks “as thick as a baseball bat?” Put some realism into the story rather than the Barnum and Bailey freak show.

oOOH Ms Sin as I will ALWAYS remember the First shemale that seduced me when i was only 18 and visiting a dirty bookstore and she treated me to an unforgetable blowjob as I sniffed her female perfume thinking a woman was blowing me as i blasted her mouth. Then imagine stepping out of the booth and just as i did she appeared with a smile. She was black and had big beautiful tits and an amazing figure. I flirted with her and wanted her phone number thinking she was a woman. She instead asked me what i was doing and when i said i had no plans she invited me to her apartment. Thinking i was going to score as a young white boy with a HOT older voluptuous Black woman had me hard and poking my pants out in an instant. And after we awkwardly made it to her apt. she invited me to relax on the couch where ahs asked me if I' like a repeat and of course I did. I kept touching and groping her as she allowed me to free her magnificent tits and play with the nipples. I was quick but not too bad lasting maybe 5-10 minutes for this Goddess and as i finished she allowed me to suck on her tits as i grabbed her as and tried to go for her pussy but she brushed my hand away and grabbed me around the base of my cock. As I was so excited and entfallend to have this chance I quickly sprung a 3rd boner and wanted so much to Fuck her. She said i could but only in the dim light and doggy style in a minute or so. Unbeknownst to me she had prepared her rear for such and occurrence and as she lifted her skirt and slightly pushed her underwear aside I was so anxious and turned on to examine anything. As I had more staying power and she would rock back into me it was hard to tell as she was so lubricated and wet but she wanted me to pound her hard and i just banged away. She seemed to be squealing allot with practically every thrust as i felt like a super stud as she urged me to go harder and as deep as i could and being already excited for having a sext black girl this whites boy put it to it. She wanted my cum and I held out for as long as i could till we were both dripping in sweat as i reached around grabbing her tits as my holding onto anchors and flickering her nipples and pinching tthem driving her crazy. I didn't know that she was cumming until I felt her pussy ass squeezing my cock as the pressure was so good and tight. I powered thru it determined to give her another orgasm as she had her face buried in the pillow just cooing like a bitch in heat. I felt like a super std and wanted to go for a fourth cum as 5 was my record and i wondered if this opprotunity would come again so i was determined to make the best of it and as she obviously was oohing and ahhing and moaning I thought she was enjoying it all. But she suggested a 69 and I not knowing her secret yet (she thought i did) so when she swung around and stuffed her 9" cock into my mouth i was aghast at and then as she engulfed mine to the root base i moaned so much hers slid down my throat as I gave her a deep throating without trying. I had NEVER sucked a cock before and Never met a shemale let alone think there could be one so Hot she would put a majority of women to shame. I wasn't as good but was so turned on and it was so new I wanted her to feel as good as I did and the residue of her cum only incensed me to slobber over it like it was my last meal. I became Bisexual at that moment knowing that it would not be the last cock I sucked and would also put me on a trajectory of being a lifelong "Admirer". Ironically we did have a few more encounters as sadly it was because she was waiting for her boyfriend to return so I knew our time together was limited. It made me sad in a way as most of the ones I met I would compare to her. She was the total package as Beautiful, well hung versatile switch and was so nice in turning me as she was surprised to learn I was her first as it made her treat me even sweeter. I even met a shemale who later became a porn star (shawna) and ironically now instead of finding one to compare I help cute twinks and femboys transition and have also turned a few married cucks into sissy bois that get dressed up and are my little bitches for the night alongside their wives. Most willingly alothough a few came along as a process of me being Dominant and bringing their bisexual side out as I had them go from becoming a cuckold into a creampie eater and then a fluffer and cocksucker eventually taking their virginity. I literally took the virginity of a younger curious bi-guy as I started by giving him a blowjob as i slid the finger in and rubbing his prostate till he had an explosive cum then not taking it out instead sucking him hard again and telling him i was going to add a second finger. as I loosened him up and had him squealing and bouncing all over i told him only ne thing was going to give him a bigger climax. He felt the dildo slidding in ant thought that was it as as he got to the edge i stopped and withdrew telling him to bend over so I could use my hand to power the dildo better. He sort of knew what was coming and once he felt me pressed to his back and me holding his arms backwards he didn't have much of a choice. I told him it could be really great or a Big Pain depending on whether he fought me as I was 6 inches and about 30 pound more and allot more muscle. He gave me just the moment in relaxing to ponder it when i slid all the way in and it was History till i coated his insides and informed him as I came that NOW my DNA was going to make him my Bitch Boi from then on and he was going to do exactly what i liked. The final seal was when he had his first sissygasm and I knew I had created a forever Bottom boy. I now wonder what he would look like in panties, stockings, a bustier and a nice wig, some makeup and heels. Naughty me doing to him what he was curious about only taking him a little further. Just like that Black shemale did to me and this young boy in Health class became a "Teachers Pet" and toy boy as soon she'll have him bound in her bed banging the cum out of him. Maybe i can get lucky and find some hotties to spitroast me or a group of shemales to have a small group like a reverse gangbang fantasy as I almost got close being with 2 at once awhile ago; but it was one after the other and not at once. Umm Liked this story and would Love to Meat Ms Sin

I wish i had found a Teacher like Her when I was in School She could have done me every day and I would have hoped I would get to do the same with her

I thought it was glorious!!! I kept thinking, “THIS is the way every young boy should be introduced to sex and given proper sex education,”

I had many fantasies about female teachers when young.at that time of my life transsexuals were unheard of by me. my loss. I would have loved to have been Greg. P.S if any trans women read this I would happily take tutoring lessens from you.