Finding a Place to Sleep in NY

My names Danny, I'm a 24 years old trainee insurance broker from Boston and this is an account of my first overnight business trip to New York City.

On a Monday morning I like to collect a coffee from a cafeteria on my way to work, a short walk later and I'm at the elevator climbing up to the 36th floor where I work.

I say hello to my colleagues and sit at my desk sipping on a coffee while the computer logs me on for another 8 hour shift dealing with other peoples accidents and losses.

I was checking my emails when I spotted an unread message from two weeks ago in my spam folder. Oh that's not good, it was from Gavin Rogers, the Head of Human Resources, who is based at our Manhattan Head Office.

Panic set in at first, I'm wondering what have I done wrong to be in trouble with HR, was it that naughty joke I told in the elevator last week, have I broken the office rules?

I opened up the message with some trepidation, it read, "Daniel, please attend a diversity training course at Head Office on Tuesday 12th April at 10:00 hours, training will be followed by a group dinner to discuss the events of the day."

Maybe I had been reported, but at least training is better than a disciplinary I thought.

The invitation gave the agenda and the names of the nine other attendee's, the branches from where they worked, and the name of the trainer, a Miss Jemima Lee.

The email was from two weeks ago and the training course was tomorrow, so I hurriedly replied back to say that I can attend and received an immediate reply thanking me for the confirmation.

None of my colleagues from our Boston branch had been invited so I would be travelling alone, something that made me feel a little nervous as I rarely leave my home state on my own.

I looked up the address of our Head Office and booked a hotel room just a few blocks away from Head Office.

Later that night I packed my clothes in a small hand luggage case, and choose my suit and tie for the next morning.

I felt a little nervous when I woke up on Tuesday morning. I shaved and showered and splashed my face with my favorite aftershave. I looked in the mirror, adjusted my tie and thought to myself, boy you look good and you smell great too.

On arrival I made my way to reception and was guided to the training room where I was greeted by Gavin, the head of HR and our trainer Jemima.

Gavin was a good looking tall black man, well dressed, and his hair was perfectly groomed. He welcomed everyone into the group and explained that the company were starting to roll out Diversity training and we were the first group to be trained.

Gavin introduced Jemima, she was a perfect 10 for me, with glamourous Asian looks, maybe she was from Korea or the Philippines, I had no idea to be honest but she was beautiful and in her late twenties.

Jemima was slim, maybe 5 feet 10 inches tall with long flowing black hair. Her short black skirt was matched with shear black pantyhose and black high heels.

Her breasts were amazing, maybe a double D cup, covered up by a thin white blouse, and she walked with a shapely wiggle of her hips.

I noticed that a few of our group were giggling when Jemima first walked into the room, and her voice was a little camp at times but she was so beautiful it was love at first sight for me.

At one o'clock we had a buffet lunch and Gavin and Jemima took time to chat to each candidate but I felt Gavin was taking more time with myself than the other candidates which left no time for me to have a conversation with the lovely Jemima.

He asked about my thoughts on diversity and my attitude to minority groups and seemed to like my polite answers. He also seemed keen to know which aftershave I was wearing?

Later that afternoon at 5pm the course was completed and Gavin arranged for a minibus to take us trainee's for dinner.

On arrival at the restaurant the beautiful Jemima sat down on my right hand side.

My heart pounded, I couldn't think of a word to say, I was completely awestruck.

I couldn't take my eyes off her beautiful body and her sexy legs, her scent was amazing too.

I had never dated a woman who wore pantyhose and I was longing to touch her hosed legs, but that would have been too risky as I didn't want to create a scene if she objected.

I did however manage to take a couple of group photos and a couple of cheeky up skirt pics. I had to wait until Jemima was talking to the person on her right hand side, then in selfie mode I quickly photographed her gorgeous legs and skirt, ideal for getting off too later I thought.

The food and drink was served and other than than Gavin and Jemima who remained sober the drink was free flowing, and to be honest I probably had one too many glasses of wine but it helped to relax me.

Once the dinner was over we returned to Head Office, it must have been about 8:30pm by then, we were generally feeling a little tired after a long day and I was looking forward to checking into the hotel and resting while having some personal time to look at the cheeky photos I took of Jemima in her short skirt and pantyhose.

Gavin kindly offered me a lift to the hotel which I accepted, and he came into the hotel with me to make sure everything was fine, but all was not. There was chaos at reception as a group of ten customers who were standing by their cases were arguing with the hotel reception staff.

A manager came down, explained that there had been a burst water pipe which had flooded six rooms and we wouldn't be able to check in today. The manager explained that all monies paid would be refunded onto our credit cards within the next forty eight hours.

I was a little shocked and asked Gavin where the nearest hotel was located and he kindly offered that I could stay at his apartment for the night. While I was considering his kind offer he grabbed my overnight bag and quickly walked with it too his car. I quickly followed and we travelled the short distance to his apartment.

I felt a little uncomfortable about this arrangement after all I barely knew Gavin but felt hopeless to turn down his kind offer, after all he was a senior manager of the company so I felt I couldn't really refuse him.

All seemed normal as we entered his apartment until I spotted that there was only one bedroom and the sofa was very small, barely big enough for two persons to sit down on, so there was definitely not enough room for me to sleep the whole night there.

Gavin explained that his partner wouldn't be home until 11:00pm and that as they had an Emperor King size bed there would be plenty of room for the three of us to share and that we could easily sleep and keep to our own space. This concerned me at first as I felt uncomfortable with sleeping with another man but after a few moments I became very excited to see how beautiful his partner was as I would be sharing her bed too.

Later on in the evening I went to the bathroom, there were blue and pink toothbrushes, perfumes and aftershave and a pair of black silk stockings hanging over the shower curtain. I now had no doubt that Gavin's partner was female and that any worries I had about Gavin hitting on me tonight were wildly off the mark.

After two gin and tonics I asked Gavin if I could retire to bed early and Gavin agreed that was fine. He said he would wait up for his partner to come home before coming to bed.

I hadn't brought any pajamas with me as I always slept in my briefs so I undressed and changed into a fresh pair of boxers from my overnight bag. I then turned off the light and climbed into the very large double bed and moved to the far end. I tried to stay awake to get a glimpse of Gavin's partner when she changed for bed but after all the alcohol I had drunk I soon fell asleep.

Later that night I was woken by voices, one was Gavin and the other a female voice. I heard the clink of glasses as they drank together and some frequent giggling. Then what may have been thirty or forty minutes later and with the bedroom light still off there was movement and more giggling. I felt the bed sheets being pulled back as Gavin and his partner climbed into bed. There was also a womanly scent in the air which seemed familiar.

I laid there all curled up and pretending to be asleep on the left hand side of the bed facing the couple. Luckily for me the female has positioned herself in the middle of the bed.

About ten minutes later I could hear Gavin whispering in her ear.

"Don't worry he's asleep," he said.

Then it went quiet, other than for the sound of a jar being unscrewed.

I could feel some movement in the bed then the sound of silk panties being pulled down over nylon stockings. Another movement of the bed and then an "Uugh, uugh, uugh, Aaaah!" She moaned softly.

It was the sound of Gavin penetrating his partner.

There was some gentle rocking and a low moan with every push into her. She was faced down, he was laying on top of her and gently pushing his cock into his partners ass. I assumed it was her pussy at the time.

The gentle fucking of the two partners made me excited and my cock became very hard indeed. About ten minutes later there was three firmer pushes into her, she moaned quietly biting the pillow below her face, then the movement slowed to nothing, and all was quiet again other than for Gavin's heavy breathing.

Gavin rolled off her, I heard her kiss him and then she moved her head below the quilt, the sound of licking and sucking followed as she sucked his cock, sucking cum into her mouth, savoring the last traces of his cum and her own scent before she turned over and faced me.

There was an aroma of sex and lust in the air and my cock was as stiff as a board. I faked a yawn then turned and faced the other way, ready for sleep, in my favorite position on my side with my knees slightly bent.

I guess she waited for Gavin to fall asleep because I felt a stockinged leg touch the back of my knee and she snuggled closer to me. I felt her soft breasts against my bare back.

Next a stockinged foot played footsie with my feet. I was so excited. Where was this going to go. An arm wrapped itself over my waist and inside my briefs and firmly held my stiff cock.

I could feel the lace of her suspender belt above the top of my briefs and the straps where they were attached to her stocking tops. This was new to me, I had never been to bed with a lady wearing stockings and suspenders. I could not see her but the feeling of her silky nylons and lace suspenders was wonderful.

I could detect the fragrance of her perfume in the air with a musky sexy odor from her recent sex.

Her hand stroked my cock. Oh boy that's just what I had needed at that moment. Then her hand let go and she gently she tugged down my briefs to below my ass. My cock sprang free.

I could feel her lacey suspenders against my back, her stockinged legs against my legs, then all of a sudden I felt what seemed like a soft cock push its way between my ass cheeks and it rested there for a while.

Her arm returned to my waist and stroked my cock. OMG I thought to myself, she must be an Asian ladyboy or trans woman. I had a decision to make, do I panic and jump out of bed and make a scene or do I stay put and see what happens and find out what it feels like to be fucked in the ass?

Then I felt the soft skin of a hard and now lubricated cock line up with my ass and steadily push forward, putting pressure onto my ring which held firm.

"Relax," she said as she applied more pressure.

My ass was being stretched and it felt like it was on fire. OMG how big was this cock, it felt like my ass was being torn in two as I felt her cock head enter my tunnel, stretch and push through my sphincter then push home several more inches.

Surely she was all the way in?

I moved my hand to behind my ass and touched her long hard seven inch cock. To my surprise and horror there was still four fingers length of cock left to go inside. Oh my how can I take any more I thought?

"Are you OK hun?" she asked in a soft tone.

While spooning me she then pushed the last few inches home. I felt like her cock was probing all the way up into my stomach.

"You like it babe?" she whispered, not wanting to wake Gavin from his sleep.

It was the same voice I remembered from the Diversity training course. Of course it was Jemima, she must be a ladyboy, that's why the other trainee's were giggling I assumed. Anyhow this was no time to ponder diversity while my ass was being impaled by a long thick cock.

"It hurts a little, please stop!" I said, and she did.

Now she rested her cock fully inside of me, giving me time to adjust to the invading cock. The feeling gradually turned from a burning pain to a feeling of fullness and later enjoyment.

She resumed her thrusting motion, slowly at first, then a little faster and then her hand left my cock and held my stomach, pulling me back towards her cock.

On each thrust I gave a low sex moan, and then after about 15 minutes it happenned, my ass started to contract, twitching, squeezing around her cock, milking her cock, she slowed down her movements and enjoyed my ass gripping her meat. My cock had earlier been seeping pre-cum and then wow!!! I came over my chest and then cum onto the sheet below. It was the most amazing orgasm I have ever had as a wave of intense pleasure spread over my entire body.

This was all too much for the lovely Jemima who's cock was being gripped by my ass and milked, another new sensation for me, her cum lubricating the inner walls of my ass.

I could feel her cock twitch and throb then spurt several times, as her warm fluid eased the soreness inside of me. She held me firmly around the waste, keeping her self inside of me for as long as she remained hard.

"Is that you Jemima?" I asked.

She said "Yes honey, I realized by the way you looked at me and then took those naughty up skirt photo's at dinner that you had a crush on me, but please don't mention it to Gavin, he's still sleeping babe."

I said "Your so beautiful, I couldn't take my eyes off you all day," and she replied

"I hope that you enjoyed your first ladyboy experience? And losing your anal virginity to me was an honor I will never forget. Your ass was so accommodating and tight and those contractions when you cum squeezed me and made me orgasm too."

"Oh yes it was amazing," I said.

"I could tell you enjoyed it, and it was immensely pleasurable for me too!"

I turned around and cuddled her, kissing her and feeling her awesome breasts.

"Can I suck your cock please?" I asked her.

"Yes honey but let me clean up first."

"No need to Jemima, I want to do the same as you did for Gavin tonight."

Gavin was still snoozing and knew nothing about my sex with Jemima or so I thought.

I put my lips around her cock and they opened wide letting her in.

I gently licked her shaft then the head and let another two inches inside my mouth until her head was close to the back of my throat.

I sucked a little cum into my mouth and there was also the taste from her fucking my ass which should have been disgusting, however this was the cock which had taken my virginity, a cock which had given me a stretching and burning pain but then immense pleasure, and it was attached too a lovely female body; I felt submissive to her lovely seven inch cock and enjoyed the experience fully.

We both went to sleep contented and waiting to see what would happen in the morning when Gavin woke up.

END OF PART ONE