From Homeless to Sexy Sissy Slut

Afterward I changed my outfit for him. This time into in white leggings and a cute black sweater and white tennis shoes. We sat on the bed together, Gary still naked. I got a warm wet wash cloth and cleaned him up.

"When I saw you I knew you'd look good but I couldn't have imagined you'd be so sexy and good sexually."

"Thank you, master." I said with a grin.

"That was just for playing. Listen, there's something I'd like you to do tomorrow."

"You name it!"

"Actually there's a few things. The first thing I want you to do is get online and find yourself an apartment preferably close to this area. I'll take care of everything. That's a priority. Second, and this is a little more daring, I'd like you to go down to a bathhouse."

"Bathhouse?"

Gary nodded, "there's one just a few blocks away. I'll meet you there but not go in with you. I'll discuss what I want in a text tonight."

"Okay, well first of all that don't have access to online. I'll have to go to the library. And what's with the bathhouse?"

"Let's take a ride, you need a cell phone and a laptop."

Going outside dressed as I was could probably have been the biggest thrill I have ever had in my life. Boys and men were turning their heads to look at me. The cell phone salesman could barely go through his whole pitch without staring and smiling. And the computer store, I know for a fact I saw one guy staring so much he had a hard on.

This was truly an amazing experience.

Gary left me that night with a new iPhone, iPad and a debit card with one thousand dollars. He said his last girl got greedy on him and one night she tried to rob him with a male accomplice. He couldn't understand why she would want to ruin such a good thing when he would've given her anything she wanted as long as she played by his rules. And he wasn't even that strict. In the end, he suffered a black eye but didn't lose any money from the attempted robbery.

Gary told me a lot about himself over the last few hours. He lived an hour north of Denver. His life was a bit complicated. Divorced, 2 grown kids, several businesses that he was mainly the financial backer. But this part of his life he had to keep very discreet and secret.

So he left me alone around 9 and I began going online. He also urged me to buy clothes of my choice.

I can't say how long I was up but it was at least 3 more hours. I received a text detailing what Gary wanted to happen the next day.

I was a little intimidated by this but I was also excited to be out. It took a total stranger less the an hour to help me find the real me. I did feel like I owed the to him but I also asked him if this is what's always going to be like, he said no. This was mainly for me to enjoy my new "self". That I had always been a boy, now I was a gurl and I should embrace it.

Then next afternoon I was entering Phil's Bath and Spa around 4:45. I had no clue what to expect from this place but I knew what Gary wanted from me. I was greeted by a man no taller than myself but he is portly and loud. Nice enough but way too loud for me. He gave me a tour starting in a spacious locker room. Lining both walls were changing stalls and a bench. To my right were showers, lining around a big shower room. Currently someone was taking a shower, but I couldn't see anyone. As we exited out the other end we were in a brown tiled hall, white walls and every 10' was a door. In all there were about 12 doors. I followed him all the way to the end which he opened a fire door and now we're in a hot brown and white tiled expansive pool room. Directly in front of me was a medium sized pool. On either side were hot tubs. Just before each hot were massaging tables. At the moment both tables were being used. Men of every shape color and size were scattered about the room. And I could see only a couple had a robe or towel covering them. The rest were all naked. Not a lot, maybe a dozen or more men. And I didn't see Gary. He could've been in the sauna.

The far wall facing us was a glass wall, steamed up but the man pointed out that's the sauna.

I noticed as we were standing there two couples of men, one engaged in oral while the other was sitting facing each other obviously playing with each other. I also took notice of one of masseuse' giving special attention to his client while another man stood close by, hard cock just inches from the clients face. But he didn't seem to notice.

The last thing he showed me was a lounge. Tv, pool table, vending machines and couches. Nobody was in here at the moment.

Finally we wound up back at the front desk in a small entrance room. He went back into a room with an opening and did some quick paperwork then asked me for ID and 75$ membership fee. My first time is free. Any time after now, 30$.

A few things Gary asked me to do before heading to the bathhouse was to paint my toenails and fingernails. My toenails I did in a nice cherry red. My fingernails, gloss. The next thing I was to do is pack an outfit for after so we could go eat. And lastly, insert the buttplug Gary had left for me. Then once I was about to go in, I was to ask for a short robe. I wasn't sure why but when I did the little man gave me a wry smile and wink then after he gave me a key for room 6 and my 2 towels, 2 wash clothes and 'small robe' he said "have a good time sweetie but be safe."

I thanked him and entered after he hit an electronic button to open the door. I was again in the locker room and I was all alone.

I was to strip naked "as per the rules of the house" and then in only the small robe I was to enter the pool house. Then I was to find a man, any man, with a big cock and make eye contact and give a knowing smile, he stressed serious eye contact. Gary explained how this is the key to scoring with anyone. Then I was to take my robe off, take a quick dip in the pool and if available, get a massage. Whoever I had made eye contact will join me. He guaranteed this.

If however there was no available table, just go to the man and get on my knees and give him the best blowjob I can. He told me in the text that I give an amazing blowjob and anyone in there would be lucky to get one from me.

He had ground rules, no swallowing, nobody allowed in my boypussy and only one man. Once I had made the guy cum he was to cum on my face. I was to then retreat to the showers, then to my room. Gary said he would find me.

I understood now about the small robe. It's a white cloth robe, pretty normal except for me, it's mid to high thigh hemline. It's a females robe.

That was fine with me I would be able to show off my smooth tan legs and cherry red toenails. I had added a silver anklet before I left.

I always found myself closing my eyes, taking a deep breath before trying something new and this time was no different. Before I walked down the hall to the pool room I did this then gathered my strength and made my way down the hall. I pushed through the door to the pool house and did my best catwalk toward the pool. Not too fast and definitely not too slow. Gary had said I will have enough attention on me so no need to give a dramatic entrance.

I scanned the room casually and there, on the other side of the room sat a dark skinned gentleman, mid to upper fifties with a grey in his thin black hair. He was an extremely good looking black man with a goatee and bright white smile. We never lost I contact and I do believe I blushed.

His confidence was obvious as he sat with his legs open, his flaccid penis at least 6" as he continued to smile at me.

I walked to the edge of the pool very aware that I had become the center of attention and I must say, I loved it!! I opened my robe, let it drop off my narrow shoulders then daintily climbed into the water. I took a casual lap up then back before I climbed out. I made a point to bend so my pink buttplug was visible for anyone looking.

Then I retrieved my robe and wrapped myself and looked over my shoulder. Both massage tables were taken but both men on them offered to move for me. I smiled and shook my head thanking them. Then without hesitation I turned on the ball of my foot and walked to the gentleman I had first noticed.

His smile was casual as I approached and neither of us said a word. I stopped just before him, leaned in and put my hands on his knees to help me kneel between his legs.

I kept eye contact as I opened my mouth and licked the head of his cock. It twitched.

Then, I wrapped my hand around the base lifting him to me and I took the whole flaccid member into my mouth. It only took a minute before I had a 9 1/2 cock fully hard going down my eager throat.

I began stroking with one hand while I made love to the head of his cock. Occasionally I would deepthroat him causing him to moan then I would go back to work on the sensitive head and underside. I worked kisses under to his balls then back again. Then I would greedily take him all in my mouth down to the base.

This lasted for awhile, our eyes keeping contact when I could. I began bobbing my head and jacking him off at the time and I could feel him begin to tense.

"I'm close..." he said in deep voice.

I sucked on mainly on the head, using my lips and tongue.

"On your face Baby." He said.

I nodded and continued to stroke him with my face just inches above his huge cock, our eyes locked on one another.

Then he shot his warm milky cum all over my mouth, my nose and face as groaned aloud. I kept stroking him until he slowed me to a halt. He was spent. I wiped my eyes, kissed the head of his big beautiful cock and got up and left.

I loved the attention I received as walked casually out of the pool room.

Gary was pounding my tight boypussy in my little room calling me his cum living sissy slut. At last he came shooting his load inside me. I felt him and pushed back to get every bit.

What had just happened in the pool room was what Gary wanted too. He wanted to watch. It didn't matter who he just wanted to watch me blow a big cock. That made him so horny he fucked me so hard in that little room.

I had decided whatever Gary wanted I would do.