WOW!!! so I have this client who absolutely loves pegging. When we first met I walked in with a few toys, max size 6" as most of the guys who contact me are just beginning to try new things- It's part of why I love my job, because I get to see that same face I saw with 3 guys in high school- the look of lost virginity and pure bliss!!!! Anyway I walked in and there were around 6 dildos and a harness on a towel on the bed. They ranged from 5x4 to get this- a 10x5 and a 8x6.5!!!! Guy can take serious bone!!!! We have fun together and have such a good rapport that we spend time together just hanging out. Well this weekend he helped me fulfill one of my few fantasies ( I'm too much of a realist for fantasizing but I'm learning- more on this soon involving a certain old flame), that of a threesome with a transgendered person. I def have desires for sex with transmen and transwomen, which is where the term "polysexual" comes in. For those of you new to this terminology please read this awesome article on
Sexis by
Freud13 called
a-cliff-notes-guide-to LGBT terms.
Okay well this woman whom we will call
X and my client
D arranged a meeting. My sloppy self gets ready and as usual arrives 15 minutes late. It was one of the nicest hotels in town and this woman has rates that match mine?! Anyway as soon as we walked in I knew she was a true professional. Within minutes she was making out with D. I instantly felt underdressed, I mean I was in jeans and a hoodie with a messy knot of hair on top of my head and this woman was dressed to the 9s in spike heels and a skin tight dress, perfume, hair and makeup impeccable, lighting,music the whole bit. I admit I was intimidated- not by her gender identity but simply by her professionalism. On one hand it was impressive and on the other a hindrance to my comfort level. I excused myself and went to the bathroom to freshen up as a nervous layer of sweat trickled across my back. A few minutes later I realized that D was nervous too when I heard him call out to ask if I was changing. I took it as a "Hey get back out here and help me" that he later confirmed.
Out of the bathroom I came in my fav trashy lingerie
peek-a-boobies cupless chemise from Leg Avenue and some cuban stockings to go with. I still felt sweaty and out of place but then I| remembered that this was all for my client and that since it was her show she was in charge, by then I relaxed.
This woman had an amazing body, she was waxed from eyebrows to toes without a hair left behind and had THE nicest, softest, creamy, tanned skin I have ever felt.Because of my style of lingerie, boobs easily became the focus and we compared hers to mine with our tongues. Mine for once were not the firmest in the comparison as she had just had them done a few weeks prior. Turned out we both have sensitive nipples. I asked her not to bite mine but she did it anyway.That was the first time that I slightly noticed her dark side or her Dominatrix personality. X also has a dungeon and does offer services to submissives that are interested. Listening to her I'm sure she does quite well but I thought it may have been wise to find out if D and I were actually into a power shift or got off on being dominated to the extent that she let loose on us.
Touching her was incredible but we both became self conscious when we realized that she had a better body than me (except the boobs of course) and was more well hung than D.. With each others reassurance we got through the hour and accomplished oral sex - given and received by all off us to all of us.
WoW she was incredible with her mouth on my clit for a good 15 minutes so that I achieved those baby orgasms, one after another but not full blown. I gave them both oral attention but what else is new? D got to give his
very first blow job and I got to watch! I grabbed a Cal Ex Couture Inspire
and worked a powerful climax out as I saw her masculinity shine through for the first time (other than her big cock of course) as she thrust herself in and out of his mouth. Yup, just like an annoying man- paying or not she did the head grab, slam her cock down your throat as you gag thing, which I know the occasional woman does enjoy- especially in BDSM circles but if my boundary against it is not respected I have been known to end the blow job and maybe the whole session. For a first blow job- a head slammer none the less he did surprisingly well. I had to giggle when I caught her dirty talk "
Ya I'm going to put an ad on Craigslist, guys will be lining up around the block to see you in my dungeon boy- $20 a pop they'll pay to fuck your hungry mouth" $20????!!! Come on give the guy more than that!
After that we all took turns with penetration- his male with a penis, hers female with a penis and mine female with a fake penis (aka a strap on) and I must say that although she was a bit rough after I assertively expressed that I don't like em big and I don't like em harsh, she still was quite an experience. I will definitely be looking for more opportunities like this in the future and am just as open as ever to sex with transwomen and transmen in my personal life.
A nite well spent!
authors note- sorry for the quick ending but I found this post from a few months ago unfinished and found it too important to not go published, nor was I willing to adlib details that aren't fresh in my mind.
My first Sinful Sunday submission 
