Homeless. But Not Helpless. (MF)

Last month, while traveling for work, I had one of those experiences that I never thought would happen to me. My job sends me out to different parts of the country to help set up new computer networks for companies. I usually will spend several weeks training their personnel and setting up the network interfaces. During this time, my company pays for my hotels, meals and travel expenses. It makes for a very lonely life. Probably why I never married or started a family.

Over the years, it was just easier to hire a prostitute to satisfy my needs and be on my way. Had a coworker of mine always said, ” You are not paying them for sex, David. You are paying them to leave when you are done.” I know it is a shitty attitude to take, but in my line of work. he was most definitely correct.

Anyway, I had just started a new job that was going to have me outsourced for three to four weeks. Normally, I will find a nice extended stay lodge or hotel so I can have a kitchenette and possible small living area. That was what I had found myself checking into one the day before my job was to start. My routine usually has me unpacking everything and then going to the local Walmart for supplies.

From time to time, I may find myself in a not very nice part of town, per say. This particular Walmart had quite a few homeless people hanging around outside. It is an unfortunate reality we live in now a days. As I was walking out to my rental car, I got approached by one of these homeless individuals. She was youngish; maybe mid to late 20’s. Dirty red and matted hair, wearing clothes that looked like they had been worn for months. She asked if I was interested in some company? Now, this was most definitely not my first rodeo. So, I knew what she meant.

I was going to say no. Every instinct told me to say no. Hell, even my nose was screaming at me to say no. However, my cock had the last say so and he was telling me to go for it. As I was putting my groceries into my rental, I asked her what she was wanting? She looked up at me and said she just wanted a place to get cleaned up, a meal in her belly, and a soft bed to sleep in for a night. And, if I was so inclined, I could pay her what I felt she was worth and she would leave the next morning. If I had not been so horny, I would have passed. But it had been several months since I had gotten laid. So, I told her to get in, and we headed back to my hotel.

During the short drive, she told me her name was Rose. She had been kicked out of her parents’ place for reasons she would not talk about. That was four years ago. Since then, she had been living with friends and sleeping on couches. However, she messed up and ended up having sex with her best friend’s boyfriend. In fact, the best friend walked in on them while he was balls deep inside her, filling her with his seed. Well, word got around to all her friends that she could not be trusted, so her places to sleep dried up almost overnight. The streets had been her home ever since.

Once back at the hotel, Rose excused herself to take a shower. While she cleaned up, I had all her clothes sent for laundry, including the ones in her bag. Then, I got on the phone and had Chinese takeout ordered and a booze delivery set up. Rose asked to use one of my razors that I had bought at Walmart. Since I like my pussy smooth and hairless, I quickly agreed. As the shower turned off, both the food and alcohol arrived. Now, I had hopes that Rose would clean up well enough for a nice night. However, the girl who walked out of the bathroom was not the same one who went in.

Rose came out wearing her hair up in a towel and absolutely nothing else. Even though I had given her a T-shirt of mine to wear. For the lack of a better word, Rose was stunning. Curvy in all the right places. Big DD tits that held up to gravity very nicely. Thin waist and round hips. The kind of hips guys like to grab onto while banging a chick from behind. And puffy pussy lips, completely devoid of hair that peaked out as she walked across to the table. She walked directly up to me and kissed me. Not a little peck on the lips like I was expecting. But the full tongue in my mouth kind of kiss.

We sat down and we both ate until we were full. Rose told me more about herself, and I gave her the Cliff Notes version of my life. Much to my surprise, she understood completely about me never getting married. Once she finished her third Jack and Coke, she got up from the table, grabbed my hand and lead me over to my King size bed. Rose pulled off her towel, letting her dark auburn hair fall down to her shoulders. As I stood there dumb founded by her beautiful body, she began to pull off my clothes.

Once she had stripped off the last of my clothes, Rose took my cock into her mouth. Using techniques that someone so young should not know, she had me close to blowing my load within minutes. I did warn her I was about to blow. Did not matter to her even a little bit. She stopped and smiled, said, “Let’s get this one out of the way. We have all night.” And with that, she resumed sucking and stroking my cock.

I grabbed the back of her head and pushed her head down my shaft as I exploded inside her mouth. To Rose’s credit, she managed to swallow every single drop as I flooded her mouth with my cum. Once I started to soften, she let go of my shaft and went to go get us both another drink. We both laid back on the bed and talked some more about nothing in particular. About the time we finished our new drinks, Rose noticed that I was hard as steel once again. She quickly deposited our cups on the side table and was about to mount my cock when I told her that I had a box of condoms in the nightstand drawer.

Rose looked me dead in the eye and said, “I have no problem using them. But you don’t need them with me. I have Turner Syndrome and can’t get pregnant. And, if you are worried about a STI, I got checked last month and have not had sex since then.” Once again, my brain was screaming “Get a Fucking Condom”. However, my cock wanted to take this beautiful creature raw and dam the consequences. And, as usual, my cock won.

Rose could tell what I wanted just by looking at me as she slowly impaled herself on my pole. Now, I do not have the biggest cock on the block, but I have been told that my girth can be painful to some. I could tell Rose definitely appreciated that fact as she moaned out loud the entire time, she rode me. Slowly, Rose fucked me as we kissed and I played with her huge tits. Once she quickened her pace, she could no longer contain herself and arched her back as her orgasm hit her hard. And me being the opportunist that I am, I quickly pulled one of her pencil eraser sized nipples into my mouth and sucked on it hard as I felt her pussy constrict around my cock.

We fucked like this through several more orgasms until she pulled herself off my shaft. Rose landed beside me with her legs spread wide. I most definitely did not need an invitation. I immediately climbed on top of Rose, pushing my cock deep inside her wet pussy in just one push. Rose wrapped her long legs around me, pulled me down to her face and said, “Now, fuck me until you finish deep inside me.” Then, she pulled me down further and pushed her tongue into my mouth.

I fucked Rose with everything I had. In fact, she had two more screaming orgasms before I finally finished and painted her vaginal cavity with my cum. Once I could breathe again, I pulled out of her well fucked pussy and laid down beside her. About that time, my work cell went off. My boss had sent me a message saying that the place I was heading to the next morning would not be ready for me for another 48 hours. However, I was under contract and would be paid regardless. I replied and said thank you. It was at this time an idea hit me.

“Rose, I don’t have to report to work for another two days. How would you like to stay with me another 48 hours?” She actually giggled and leaned over to kiss me. “Would love too. What are we going to do to entertain ourselves for two whole days?” she said with an evil grin. Little did I know that one little text message was going to change my life.