Diary of a TS Call Girl (Juicy Moments): Chapter Three-Marathon Night!

[TSFantasia]

Well this happened night of Sept.17th day of Sept 18th. Some of the girls will laugh cuz this is a typical night for them lol.

I had a confirmed 3 hr appt with a guy coming in from out of town on Wed. from 11-2. Tuesday had been dead then at 9:30 got emails then texts from a guy I had seen once before at a hotel over a year ago. He had emailed me a few times before wanted to get together for an evening but never seemed to follow through. He lives 1.5hr away but had the "boys night out" and "drinking with buddies going to crash here" excuse going and I obviously popped into his mind. He wanted to come see me and spend the night. Told him what that would cost and he was ok with that. He wanted me to come meet him half way and drive his truck in. I said no but would meet him at a strip mall parking lot right at the edge of the city along the route he was coming in from and drive him from there. Picked him up about 11pm swung by the ATM got my pymt up front stopped by the Off Sale for a case of beer and headed to my place.
We headed upstairs with a few cold beer each to start and got a little caught up before starting to make out. Last time I saw him we mostly did mutual oral and he blew me as he finger fucked me til I blew in his mouth...mmm that was good . He had already told me that he really wanted me to top him for his first time. We DFKed he made his way down and spent a good while sucking on my cock and balls. When I was rock hard I said "Ok Hun lets strike while the irons hot" (I always say that lol). So I put on a condom lubed up his tight little hole and told him to straddle me which he happily did. I find this a good starter position for newbies, virgins as they can grab hold and guide it in and determine how fast and far they can take it. I let him enjoy him self riding my cock while he squeezed my tits and tugged on my nipples. After a few mins of that I suggested he roll on his back and let me fuck him like a little bitch. He did and I fucked him missionary and stroked his cock which seemed to be struggling for erection ( you know how it is guys your body blood flow is saying "Are you a pussy or a dick? make up your mind!" I did that for several minutes til I ran out of steam. I pulled out and immed. went to giving him head while he watched . He got hard quick and wasn't long before he said "Im going to cum!" which i let him do all over my tits. Then laid back beside him and smeared his cum all over my breasts and belly..... to be continued this is a marathon remember

[TSFantasia]

...so we lay there for abit while he soaked in his post-orgasm bliss and his cum slowly dried on my breasts and belly giving me that just waxed shine ..lol. We were watching shemale porn (of course) and soon we were french kissing again and he again made his way down to my throbbing cock . He kissed, licked and sucked on my cock and balls and I was rock hard again I told him to finger fuck me , which he did. Felt great but wasn't quite getting there so I reached over to my nightstand drawer and pulled out my 6 inch dildo vibrator. "Here use this on me" as I handed it to him. He seemed to be enjoying watching it sliding in and out of my shemale pussy. Then I put my hand on the back of his head pushing his face back onto my cock. Felt great but he stopped sliding the vibrator in and out of me the way I like it so I took hold of it and told him to concentrate on my cock. I began to gyrate and pump my pelvis simultaneoiusly fucking his mouth and fucking my pussy with my vibrating dildo hittting the g-spot I said" I'm going to cum!" and then twisted and convulsed as I did. Pretty hard to keep my cock in his mouth while I do that but he did the best he could as cum squirted in his mouth, on his face and hand and on my belly. I felt my body relaxed and lay back vibrator still buzzing in my pussy and just started to laugh (I do that when I have a great orgasm). After I regained my composure I pulled the dildo out and turned it off as he lay back beside me wiping the cum off his face and hands with a towel I then applied the 2nd coat of "cum wax" to my belly and breasts.......

[Rockheart]

Nice read, lots of finger fucking and cum flying, just the way we like it.

A little bit of local flare is interesting too.(Trucks and Offsale)

I am anticipating more finger fucking and blowjobs!

[TSFantasia]

...so it was getting to be about 1:30-2am I asked "so when do you have to be at work?" Expecting to hear something reasonable like 8 or 9. He said "7:30" "Oh and how long does it take you to get there from here?" "About 1.5 hrs" "Well guess we should get a little sleep then I will set the alarm for 5:30" He agreed and we both quickly fell asleep in the spoon position..I was the little spoon lol. I woke up to him running his hand over my ass and feeling my slit then reaching around and starting to fondle my cock and balls. I continued to act the sleeper while he worked at getting me hard I could feel his hard cock pressed against my butt cheek. I was just about to hand him a condom and lube myself but when he knew I was awake he pulled me towards him continuing to pull on my cock which was hard again. He then turned his back to me pulling my hips toward him. Ok I've created another "bottom monster" lol. "Just a min" I said as I rolled over grabbed a condom & lube put it on quick and let him grab it and slide it into his not quite virgin (anymore) man pussy. I thrust my hips as he grinded down I reached around and grabbed his cock and stroked it and let it slide through my clenched lubed fingers. I whispered in his ear "Yeah you like that shemale cock spreading your little bitch pussy open don't you? He moaned "Yes feels so good!" Surprisingly it didn't take him long to cum which he did partly on my hands, his belly and probably the sheets ..oh well he has to sleep on that side . I handed him a towel and jumped up to wash up in the bathroom. Climbed back in bed and said "Ok sleep now!" Looking at the clock it was about 4am.
Short nap and the alarm was going off at 5:20 hit the snooze a couple times. Then said "Hey time to get up..I gotta go peee be right back" Came out thinking he may want a quickie morning wood fuck meaning ME GETTING FUCKED lol but he was already dressed and gathering up his stuff. I got my sweat pants and t-shirt on grabbed a hoodie and said, "Ok let's go"
Got him back to his truck before 6 am hugged good-bye returned home and fell back into bed set my alarm for 9:30 to see if my 11am was going to confirm or not....zzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz zzzzzzzzzzzzzzzzzzzzzzzzzzzzz.....

[Franklinzed]

Damn that's pretty hot! Lucky sob


Sent from my iPad using Tapatalk - now Free

[TSFantasia]

.... I woke up at 9:15am to the sound of my text notification and once my eyes could focus I looked at my phone to check for texts. Sure enough there was my 11am appt "Hi are we still on for 11am?" I looked longingly at my pillow then replied "Yes 11 is good :-)" He replied "And I did want you from 11-2 is that ok?" He was coming in from 2.5 hrs out of town so was obviously already obviously was already part way to Regina. I told him to text me when he got into town to get my address and directions.

I started a pot of coffee and jumped in the shower, redid my makeup and picked out an outfit . Then had time to relax with a few cups of coffee. Looked at my emails always a few from 1;30, 2:30, 3:30am guys wanting to get together. Lol I don't take those seriously just guys stumbling out of bars horny . At 10:15 he text to say he was in town picking up a few things and would be over for 11. At 11 sharp he was at my door I met him in my Black/hot pink embroidered bra and panties, thigh high silk nylons, black 5 inch heels, and wrapped in my black with pink trim stain robe. He was stocky guy about 6ft and in his 50s. His hands were full of bags and a flower bouquet. I gave him a hug and welcomed him in. He said he didn't know what to get me so flowers seemed like a good idea. "Awe thank you so much!!" (This is my first flower bouquet from a client).

We headed upstairs and got comfortable on my bed I asked him what was in the bags and he started to share about his crossdressing fetish and if it was ok he would put some of them on after abit. I said sure that would be fine. We started to make out and his breathing got heavy as he french kissed me and began to explore my body with his hand. He unsnapped my bra and began to squeeze and caress my breasts then kissed my neck and started to really enjoy sucking on my nipples. He had gotten down to his boxers and I just lightly ran my hand and fingers over his back and butt and across his crotch felt that he was already very rock hard. I like to let the guy explore and enjoy my body for sometime before I start touching their cock as if a light touch causes their cock to twitch I know they are ready to explode right there and have guys do that several times.
He was really enjoying himself and kept complimenting me on my looks and body. His hand moved down between my legs and i told him just rub it like you were rubbing and massaging a woman's clit, which he did. I really enjoy this type of foreplay so many guys don't spend any time on my breasts and are in a hurry to get my shemale clit (thats cock ..lol) out of my panties and into their mouth makes me wonder why I have tits sometime! .....

[TSFantasia]

Balls deep in a cross dresser

...After sometime of him enjoying my soft, semi-hard to rock hard cock in his mouth he asked if he could get some of the things he bought on and if I would top him. I said sure. He put on a rose with black trimmed satin corset, a sort of matching silk and lace crotch-less panties, some black silk nylons and some slip on high heel shoes. I lay there continuing to stroke my cock til he climb back on the bed. I asked him to resume sucking me til I was rock hard then grabbed a condom and rolled it on. I told him to roll over on his side butt towards me. I lubed him up and tried to enter him spooning style but that did not quite work. So I told him to pull one leg up towards his belly while I straddled his other leg and found his tight little cherry lubed hole . I slid in fairly easily and did not take long before I was balls deep in him not that hard I'm only 5.5 ..er I mean 7 . I kept a steady pumping action on him told him what a pretty bitch he was and how good his tight hole looked wrapped around my cock! I squirted some lube on his cock and balls and began to stroke his cock in time with my strokes. He moaned how good it felt and wasn't long before he said he was going to cum. I pulled his cock up and back towards me so it squirted on my legs and his and not all over his pretty new corset . He just lay back breathing heavily saying "Wow, wow, my legs are shaking!" I told him just to relax and enjoy it as I grabbed a towel and wiped the cum off my leg and his. Then lay down beside him my head on his chest running my hand lightly over his belly and thighs.
After about 10 mins of just relaxing he went to clean up abit in the washroom and I did too. We lay down again chatting about his crossdressing experiences and shared some of mine. He was a sporadic CD buying somethings to enjoy dressing in when he had the opportunity and then usually throwing everything away lest the wife find his stash. We started to make out again and his hands squeezed my breasts and again made their way down to play with my clit followed shortly by his mouth. We moved into a side by side 69 position and sucked on each other. I was rock hard again he was at about half mast. I told him to finger my slit which he did felt great with his large thick fingers. I did the same playing and fingering his ass which caused him to get harder. I knew he wanted me to cum so I reach for my vibrator and slid it in me and worked it in and out while he continued sucking and stroking my throbbing dick. It didn't take long and I told him I was ready to cum so he had a few seconds to decide what he wanted to do. He let some of it squirt in his mouth then stroked the last few squirts up towards my belly one came up over my right breast and realised later theat some of it landed in my hair. Was kind of surprised by that see the night I had already had but enjoyed it all the same. He was propped up on his elbow gently stroking my cock and rubbing the cum around my groin...

[TSFantasia]

Cross the Finish Line Already!!

OK someone reminded me that I hadn't finished this Diary entry. Guess I passed out at the 20km marker .

So after relaxing for a bit my cross-dresser friend wanted to try on a few other things he had bought, mainly some thigh high latex stocking/leggings. He was heavier set and already overheated. I told him he was going to sweat like crazy in those. He agreed but since he had bought them wanted to try them on anyways. He asked if I would top him again I looked down at my half-masted dick, still oozing last few drops of cum from my massive orgasm 15 mins ago. "Well I think I will have to use a strap-on." He was ok with that so we picked out a size that he felt comfortable with. I did him missionary and doggie style. After 5 mins or so he said he wasn't going to get to an orgasm like that. So I went to oral on him and soon he was hard again and shortly after that he came on my tits.

We relaxed and chatted abit more then he said guess he should shower up and head home (2 1/2 hrs away). He had his own bar of soap and said it was so he smelt the same way he left home. Hmmm smart guy! Attached guys take note women are very sensitive to scents so if your SP is wearing perfumes, etc better to take a shower before you go home and give your wife/gf a hug . I asked him what he was going to do with the CD stuff he had bought (about $200 worth) he said probably just dump it. I told him I would hang onto it for him for next time . He liked that idea. In case you think I'm making this stuff up pic at bottom shows his stuff. The pink corset is his the black one in the corner is mine for comparison and also his size 13 black shoe next to my size 8 creme colour shoe

He had just left and an email came on my phone from a guy I had seen a few times before. "Are you available for an appt this afternoon?" I looked at my pillow then replied, "Sure, how about 4pm?" It was almost 2:30. He said, "Sounds good see you then!". I showered & freshen up my makeup and had a quick power nap. Shorten this one...it was a GFE session so we kissed, caressed, had mutual oral, I topped him for a few mins and then rode him until he orgasmed. I did NOT cum...I'M SORRY!! LOL.

[cameeindos]

wow your stories are hot.