Room Service

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A shemale has a seductive sexual encounter to remember.
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sissy77
sissy77
137 Followers

It was a cold winters evening. I was in the bath tub running a hot water bath with bath salts, relaxing for the night. A razor lay astray, having freshly shaved my entire body.

Who am I you ask? I am Rose. I was born Ron, but realised early that my body and mind did not match and it did not take long for me to transition to Rose. I am 25 years old, having an amazingly feminine body and face with curves at the right places, long mid back length straight natural brunette hair and breasts to die for, C cups thanks to Dr Henley's expert surgery. Nobody could tell me from a girl until they touched me down there, where lay my 3 inch dick. I was saving up for surgery and therefore had to live with it until I got rid of it.

It was 6:30pm when I decided to come off. As I entered my heated bedroom, I saw I had received a new email on my laptop. It was him, the gentleman I was going to meet tonight. A craigslist ad and a few exchange of emails and pics later, we had decided to meet up tonight for an experience that made a mind blowing memory. The new email read 'Four Seasons Room 1902 9pm. See you soon.' I acknowledged his email and got down to work.

I picked up a red lingerie that accentuated my figure, with matching garter belt and panties as well as stockings. Make up followed after with smokey eyes and a blood red lipstick to match the theme. I then blowdried my wet hair and straightened it. It fell beautifully over my shoulders and onto my breasts after I was done. I looked nothing shy of a seductress. I then went on to insert my metallic butt plug in my ass. The cold sensation made my tiny cock tingle and I ached thinking about what the night held in store for me.

Once done, I took my fur coat and headed downstairs to the living room that already had the fireplace going on. Winters get extremely chilly where I live and the open lingerie did little to nothing to keep my bare skin from getting cold. I poured myself a glass of cabernet sauvignon, a gift from my previous experience with another man. It was 7:45pm and would take me an hour to get to the hotel from my place, a cab was on its way as I booked one and now I waited on the comfort of my couch by the fireplace relaxing sipping on some fine tasting wine.

The cab arrived at 8. I put on my fur coat and hopped on. All the way, I kept imagining about how things would go down. My heart started beating faster and although I have had sexual experiences through craigslist earlier, I always get anxious. The closer we were to the destination the faster my heart raced. It started to snow on my way there and as the city lights passed by the whole atmosphere had a touch of romance in the air. The bluish dark night sky, the falling snow flakes, the view of couples walking arm in arm on the side walks keeping each other warm, the contrast of the amber lit houses to the stark white outside, everything made the trip magical. I arrived at 8:55pm.

The grandeur of the 5 star rated hotel added to the experience. I went on to the reception and was greeted by a friendly young 20 something boy. I asked him to inform the gentleman of my arrival. A quick phone call later, I was on my way up in the elevator, the moment drawing close.

I arrived at the door, took a deep breath and knocked. When he opened the door, I was floored. I had only seen his faceless pics and I knew his muscular body was amazing but his face made my jaw drop. Chiseled jaw, blue eyes, well set hair and a smile to die for, he invited me inside. As He turned around, I quickly took a glance at his tushy and I wanted to grab it badly but I controlled myself.

He then said, "I hope it was not a lot of trouble getting here. Also, I must say those pics of yours were amazing but you in real life are a goddess."

I blushed.

I said, "You too are a very handsome gentleman."

I tried to stay subtle in my compliment but in reality my cock was already hard just looking at him.

"Please be comfortable. Would you like a drink?" he asked.

"Red wine please if there is one available." I replied.

He checked the bar and found a bottle of shiraz, poured 2 glasses, handed one to me and sat on the one seater couch across from where I was seated on the bed. A soothing conversation followed where we got to know a little about each other. He was a recently divorced 35 year old who worked for an architectural firm. It was his first time with a transgender and his tapping feet clearly showed signs of nervousness. A few glasses down, I decided to calm him down. I got up from the bed, took off my fur coat and that is when his jaw dropped this time.

I slowly walked up to him, my heels making the distinct tapping sound. I stopped right in front of him. I grabbed his hand and said,

"Okay so get one thing out of the way, here feel it," I said.

I guided his hand onto my crotch.

He felt my hard on through my panties and rubbed it from the outside. I then sat on his lap and for a few seconds just looked into his blue eyes deeply. It showed pain, hidden by a fake smile that he put up. Perhaps the pain of divorce but I wanted him to forget it all tonight.

I gave him a quick peck and caught him by surprise. He then brushed the hair off my face and landed a deep passionate kiss on my lips. It was one of the most romantic kisses I had ever had. We made out for a few good minutes before he started moving his kisses on my neck and worked his way down to my breasts and now erect nipples. He undid my bra and went on to make love to my breasts. He kissed my nipples, gently bit them and softly pressed my breasts. My moaning gave away that I was enjoying his work. He then without warning just lifted me off the couch and carried me in his arms, my arms wrapped around his neck. I felt so submissive and protected at that moment. I kept kissing him before he lay me down on the bed.

As I lay he moved towards my belly and then my crotch. He shifted my panties and stroked my cock gently before giving it a peck.

He then said, "Will take me some time to get used to this hahaha."

I barely acknowledged him as I was growing hornier by each passing minute. He then decided to work on my ass. He slowly pulled out the butt plug and made me suck it a few times. I oblidged. I was completely under his control at this moment. He licked my opening a few times and then gave me the most amazing rim job that I later nicknamed the 'tongue tornado.' He was at it for quite a while and had it not been for my horniness reaching an all time high that it made me crave his cock badly, he would not have stopped.

I pulled his head away, shimmied down the bed and gladly went down on my knees. He pulled off his tshirt revealing his abs and cut body. I undid his jeans and undies, and there hanging right in front of my face was an alpha schwang unlike any other I had seen other than on porno. It was a good 8 inches and so thick that it was impossible to wrap my fingers completely around it. I wanted to make love to it like there was no tomorrow.

I looked deeply into his eyes and gave his cock a lick on the tip followed by the whole shaft and the balls too. He shivered when the wetness of my tongue tickled his balls. I then part my lips as his dick, in all it's glory entered my eager mouth. I started building up rhythm sometimes sucking deep and slow and sometimes sucking only the tip fast. I kept swirling my tongue around the tip and that made him groan. I could taste his sweet nectarlike precum. As I sucked, my long hair covered my face and he gently grabbed all my hair in a bunch so he could see my mouth do an amazing job on his now red and hard cock. Amidst all the groaning, he finally decided to speak.

"Gosh that is the best head I have ever had," he said.

He picked me up, turned me around, put all my hair on one side and passionately kissed my neck once again. While doing so, he also grinded his hard member on my ass, similar to a hotdog rubbing between a hotdog bun. He then walked me in front of this full length mirror on the wardrobe door, bent me over and started lubing my ass up (I brought one with me). The cold sensation of his fingers readying my pussy turned me on so much that my small cock let out some pre-cum.

I said, "David I can't wait to have your cock in me."

"Coming right up babe," he said.

He called me babe. I giggled in my mind a little. The horniness took over as he finally placed the tip of his eager cock at the entrance of my hole, ready to explore the depths of nirvana.

The initial pain didnt last long and was taken over by a deep intense pleasure I had never felt like before. Maybe because I felt a certain emotion I couldn't describe to myself back then. His slow in and out thrust had already started building an orgasm inside me. My loud moans were cue to build up his pace and he fucked me hard and so good. He held one of my arms behind my back and kept pounding me. I looked at myself in the mirror and never felt this submissive ever. Our eyes met and I could see David enjoying every bit of this, his initial nervousness completely disappearing with each thrust. I bit my lips so hard.

He then let my arm go, pulled out, pulled me off the mirror and picked me up completely off the ground once again and impaled me with his 8 incher once again in the same position, me now bouncing up and down his cock. I was in cloud 9. David was the perfect package, good looks, great bod and an amazing lover. Yes! A random stranger from craigslist that I barely knew felt like a lover to me already. He fucked me in the same position for a good 10 minutes before he placed me on the bed, his cock still in my ass.

The fucking continued. Being in missionary, I saw my ass devouring every inch of his beautiful cock for the first time. Oh it felt so perfect.

"Yes baby, keep fucking me like this, I have never felt this way," I said.

"Oh God! That ass is better than any pussy I have ever fucked!" he exclaimed.

He then turned me around, got me on all fours and started fucking me doggystyle. The sound of his thighs, hitting my cheeks resonated throughout the room. My moans had reached a point where even the guests in the next room would get a earful. He grabbed all my long straight hair in a pony and fucked me deep and slow, hitting all the right spots.

"Oh God! Baby I am going to cum," I said.

And a few thrusts later my tiny cock started leaking cum all over the bed. every thrust brought a little more cum out of my cock. There was now a pool of my own cum on his bed.

"U sure cum a lot," he said.

He then went on to shift me on the bed so that my face aligned with the pool of cum. He pushed my head on it and continued fucking me doggystyle. I lay in my own cum, still getting fucked by his meat, no signs of him cumming yet. While I was being fucked I started lapping up the cum. The sweet salty taste and the fucking together built up another orgasm in me waiting to happen. I made him stop after a little while and pushed him on the bed now as I got on top of him.

I held his cock and glided it in my boipussy, now being in total control, riding his cock classic cowgirl style. My hair was in his face and he grabbed all of it, held my head, brought me closer to his face and kissed me passionately, deeper than I have ever been kissed, with emotions I never felt before.

"I am going to cum baby. Where do u want it?" he asked.

"Cum in me David, I want to have your seed all in me," I said.

I rode him up and down a few more times and could now feel his dick pulsing in my ass. The pulsating dick made me feel a warmth in my ass as cum started gushing inside me. He came so much that my ass could not hold anymore and it started to dribble out even before he pulled out. I slid off of him and lay next to him, sweaty and with an ass full of cum. I took a scoopful of cum from my ass on my fingers and licked it. The sweet salty taste overtook my tastebuds and I felt so touched, for the first time while tasting another man's cum.

"Thank you," he said.

"You dont need to thank me," I said.

He said, "I actually do. My divorce had riled up my confidence and pushed me into depression but you put me at ease today. U made me feel so loved once again and I have forgotten all my sorrows for the first time since my divorce. Thank u."

"I am glad I could help," I added.

Not knowing what to say anymore, I told him I should leave. He then spoke lovingly once again.

He said, "Rose, you are better in bed than my wife. The best love I have ever made. I know its not my place to ask but would you mind spending the night with me. I feel deeply and emotionally connected with you and I dont want this to end. Infact, I want this to be a beginning of our relationship."

I was stunned. For two facts. No one ever wanted me to stay after and second that he wanted this to turn into a relationship. Had I not felt those emotions I felt earlier with him, I would have said no but even I deep within wanted this. I did not want this moment to pass. I wanted him more than just fucking. I wanted to be involved with him emotionally.

"Yes. I'll stay. I too feel something for you David, something I never did before. I was always treated as different but u make me feel like what I truly want to be. A woman. I will gladly stay and as for our relationship, lets talk about it tomorrow. For now, let's just be in this moment," I said.

I then went on to kiss him again and stroked his cock until he was hard once more. I sucked him off for a good 15 minutes until he came all in my mouth and I swallowed every single drop. I lay next to him once again.

"Wanna cuddle?" he asked.

I giggled and nodded and turned my back towards him, becoming the little spoon. He held me tightly from behind and whispered something into my ear that I wont ever forget.

He said, "This is the best room service I have ever had."

I smiled. We both drifted off to sleep.

THE END for NOW.

Rose will Return.

sissy77
sissy77
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AnonymousAnonymousover 5 years ago
Amazing, I can see this easily being the start of a few chapters

And if you decide to pursue that, I know I won't be the only one reading them!

CasanamiCasanamialmost 6 years ago
More please

It was amazing I would love to read more

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