As far as motel rooms go, this looked like a very nice one. The mattress appeared to be new, the décor was very modern, and all the light bulbs worked, at least the ones that were turned on. I was making these observations while a truck driver named Jerry was fucking me doggie style, carrying on about how I was his “little princess slut” and “little baby fuck hole.” I could only imagine that where Jerry was from, both were wonderful terms of endearment. However, the only thing “little” in the conversation was Jerry’s penis. It was a penis which, even when fully erect, was only about four inches. Poor Jerry was really the little one in the room.

After Jerry came, he produced another one hundred dollar bill and asked me to stand in my bra and panties next to the bed telling him how naughty he was while he jerked himself off. While not very well endowed, I would give Jerry credit for staying power. As he was about to cum, he called for his slut to come and take his cum shot in the face. I did as he requested, and after moving into position, felt his cum shoot on my nose and cheeks and then slowly sliding down my face. Just over sixty minutes after arriving, I had freshened up my face, was zipping up my knee high boots, and heading out the door four hundred dollars richer. Jerry was lying on the bed talking to himself about the “best night” he had ever had in his life. I let myself out.

I didn’t make it to the bottom of the staircase when Amber, my street friend and confidant, came running around the corner of the motel looking for me.

“Oh, thank god. I thought the cops got you!” she yelled.

“What the fuck are you talking about?” I asked as I was adjusting my panties under my skirt.

“Undercover cops out tonight. A bunch of girls over on Fifth got scooped up. I would be really careful tonight.”

I gave Amber a hug and told her to be careful as well. She headed back to the street, and I was walking straight for my car. In the four blocks I had to walk, two squad cars drove by, one unmarked car slowing down to look my way, the second turned around and headed back toward me. I didn’t want to draw attention to myself by turning around to look but within seconds the car pulled up alongside of me slowing down to my pace. If the black mini skirt and boots didn’t scream “street whore” I’m sure the hoop earrings and the sheer top did the trick. This was not what I needed to happen.

As quickly as they had pulled up next to me, they sped up, turned their lights on and did a U-turn. They sped off in the opposite direction. I made it back to my car safely and exhaled. Jerry was my fourth trick of the night and the most profitable. I counted out my money to the tune of six hundred and twenty-five dollars for four hours work. Not bad for a college job. As I drove home though, I started to think about risk and reward. This was a great night, but others had been much less profitable. The police scared me. All it would take is one bad night and I’d be fucked. What was supposed to be a one time dare in the pursuit of meaningless sex, had turned into a two month exploration in the world of street prostitution. With graduation well within my sight, I decided it was time to pull the plug and start to move forward with the rest of my life. By the time I arrived back at the apartment, I had firmly decided my prostitution career was over. At least for now.

*****

I felt I needed to reconnect with Sal and Sophie and apologize for being incredibly absent the last two months. I don’t really think they had any idea of the dark hole I had jumped into, and I didn’t even know where to start trying to explain. Sal and I hadn’t seen a lot of each other and when we did, he usually commented on my weight loss and asked where I had been. I hadn’t seen Sophie in over a month. The next day, Sal and I had a cup of coffee before heading out to class. I spilled the beans on my whereabouts. He was in shock at first, but he quickly became very inquisitive about my experiences. I went on with a detailed accounting of some of the best and worst nights, ending with a good laugh. I asked about Sophie. Sal said she had been going back and forth to home quite a bit to interview for jobs and to help her brother with some things. I swore to him that he would get his roommate back and my days as a working girl were over.  

That weekend, Sal was working Saturday morning and had to drive home for an award dinner honoring his uncle that night. Since he was driving straight there, Sal came home and got all “tuxed up” for the occasion. He and Sophie were obnoxiously cute together when they wore sweats. I could only imagine how great they looked together all dressed up. He was off and said he wouldn’t be back until Monday morning. That would mean I would have two days to myself. It was perfect for the sexual detox that I felt was in order.

After a great afternoon workout, I came home, had a bite to eat, and pampered myself with a relaxing bath. For the first time in a long time, I was very content to just chill. My mind wandered as I lay in the tub. I was thinking about the last few months, my pending graduation, and the real world that was ahead of me. Even with all of these other things that occupied my thoughts though, I couldn’t get the image of Sal in his tux out of my mind. He was very Italian, traditional, and very handsome. I always thought he was a good looking guy but never thought about him in a sexual way. Until that moment. Lying in the tub, I couldn't get my mind off Sal.

As I was drying off, I was debating what I should wear. While sitting around in a tee shirt and shorts being a dude seemed like a great idea, I found myself sliding into a pair of white panties and shortly after, fastening the clasps of a white lace bra around my chest. I sat down at my makeup desk and figured there was no need to go all out with my makeup, but my face felt naked without it. As I sat in front of the mirror applying mascara to my lashes, I found myself getting turned on thinking about Sal.

I eyed a certain black cocktail dress and heels in my closet. I even laid out a garter belt to add a little extra spice to my attire. But I promised myself a casual night and ultimately a pair of black leggings and a loose fitting sweater won out. As I opened a bottle of wine, poured a glass, and fell into the corner of our couch, I knew I had made the right call. I slowly had a few glasses, listened to music and around 11pm was more than ready for bed when I heard a key being put in the front door lock. At first, I was thinking Sal and his girlfriend had come to spend the night, but I was surprised when it was just Sal.

He grabbed a beer out of the fridge walked to the living room and gave me a look as he plopped down in the chair next to me.

“Well fuck, you look cute, don’t you?” slightly slurring his words as he took a drink from his beer. "Oh and good, you're drinking."

“Thanks. But what the fuck are you doing here? Where is Sophie?”

“Sophie broke up with me, at her house, when I was there to pick her up for this stupid dinner I had to go to. Of course, had you been around the last few months instead of pretending to be a hooker, you may have known we were having trouble.”

“Fuck you for that. But you're right, I had no idea, and I’m sorry.”

Unknown to me, things had been falling apart with Sal's girlfriend and she chose to break the news to him that night. He didn’t take the news well. I had stopped drinking my wine long before he had finished his fourth or fifth beer, trying to help him talk through his situation. Finally, we decided we would pick things up in the morning.

“Well, I’m not sure your family would have accepted me as a replacement, but you should have called. I actually had something a little more formal all laid out to wear just in case.”

“Bullshit. You just thought you’d have the weekend to play dress up, or whatever it is you do, by yourself. Because you thought I’d be gone and thought I don’t dig what you do. I admit, I didn’t get it at first. But fuck man, you are really convincing as a chick. And if dudes were paying you for sex? Fuck man, who am I to judge?”

Obviously, Sal was drunk.

“So go, get on with what you were going to get on. Let’s see what you got for me. I mean you look cute but let’s see some sexy.”

I told Sal to wait right there and went down the hall in my room to change. I tried not to take too long changing into the little black dress I was eyeing once my garter belt and stockings were in place. I slid into a cute pair of heels and sat at my table to touch up my make up. I figured I was in the room for at least fifteen minutes and that there was a good chance Sal would be passed out by the time I finished. He was not.

“Holy shit. You look really fucking hot,” he said. And then he just stared.

I did look great and still felt a little buzzed. If there was ever a time to be with Sal, maybe even just suck his cock, this was it.  

“I must admit, I was almost ready to just chill in a shorts and tee-shirt and give 'being a girl thing' a rest for a while. But these past few months have made me realize how comfortable I am when I’m like this. Before I knew it, I was made up and sipping wine. I figured this dress was a little too formal for sitting around.”

“Oh man. Amazing. You look amazing. But yeah, OK.”

"OK. Yeah, here we are."

There was a moment of awkward silence as I sat down across from him. I wanted to kneel in front of him and suck his cock so bad. I imagined him shooting a load of cum down my throat and me swallowing every drop.

“I think you should go to bed Sal," I said as I put my hand on his thigh. "Sleep this off and we’ll sort things out for you in the morning.”

He put his hand over mine, paused for a moment, and then nodded in agreement.

We said our good nights as we both walked into our rooms. I admit it took everything for me not to follow him into his room. However, I left my door slightly ajar, figuring if he were at all interested he may just wander over. I had a feeling the night wasn't quite over. Maybe he would find the open door inviting enough to come in. I could hear him mulling his room for a minute and then there was silence. I took off my shoes and was unzipping my dress when he walked in.

“I am so sorry for ruining your night,” he said before rambling on about how technically, his night was ruined as well.

“Why don’t you make it up to me and help me with this zipper. It’s a tricky one to get undone,” I said with a laugh.

He walked in and took the zipper in one hand, held my shoulder with his other and slowly worked it down my back. I turned to face him.

“Thank you for being you. You’ve been a great roommate; I’m sorry about the last few months, and I really hope you and Sophie can work things out. And we should really both get to bed.”

“God damn. I seriously never realized how hot you are.”

I knew Sal was wasted but when he put his hand on my shoulders and my dress dropped to the floor, I knew this was going to happen. I stood in front of my roommate in my garter, stockings, bra and panties. I reached to touch his chest looking him in the eye and then slowly glancing down to the obvious bulge in his pants.

"Virgin white?" he said with a chuckle as he ran his finger down one of the bra straps.

“We really shouldn’t” I suggested.

“Really shouldn’t what?” he answered taking my hand and moving it between his legs. “So you would fuck a complete stranger, but you wouldn’t fuck me?”

My hand could feel his cock growing in his pants. I closed my eyes for a moment before closing my palm and fingers around it, softly squeezing my grip on it. I could feel him getting harder.

“Listen, it’s not about me wanting to fuck you,” I said as I slowly stroked his cock over his pants. “It’s about if you want to fuck me. Don’t do it if you’re going to regret it in the morning.”

He answered by undoing his belt and starting to take off his pants. I let go of the light grip I had on his cock and helped him get them off. His big hard dick was sticking through his boxer shorts. I had seen him naked before and new he was well endowed, but I had never seen him erect. He looked to be at least eight or nine inches of beautiful cock. I slowly slid his shorts down to the floor and remained on my knees in front of him.

I started to stroke his cock and looked up at him. “We can’t walk this back. Wherever this goes, it goes. And tomorrow? Tomorrow is a new day.”

Sal’s only response was to pull my head toward his throbbing hard on. I willingly took as much of his cock as I could, enjoying the moment more than I think Sal knew. I sucked his cock, licked his head, and ran my tongue across his balls for a few minutes before standing up and taking him by his hand.

“I have always wanted you. All of you. Tonight, I get what I want,” I whispered in his ear as we both collapsed onto the bed.

Sure, I lied. But in the moment there was no other thing that I wanted more than to be with Sal. His cock was perfect. His body was toned and muscular. As we kissed for the first time, my hand found his cock again and started stroking it. After minutes more of kissing and touching, I slowly started licking down his chest and stomach. I licked around the tip of his cock and softly took his head in my mouth. My lips kissed gently against it before sucking down the shaft. I sucked up and down his shaft before deciding to suck on his balls. After taking each one in my mouth, I came up for air.

“How far are we going to take this?” he asked.

“All the way. Or seriously, get the fuck out now right now and go to bed.” I was not messing around. Neither was Sal.

Sal answered with a much more forceful kiss than before, pulling me back onto the bed.

"Oh Mr. Tough Guy now?" I asked with a spry smile hoping he would take my hint that I was perfectly fine if things got more physical.

He pushed me down and held me around my neck as he forced his tongue into my mouth. I moaned in delight and willfully accepted his advances. My hand found his cock again as we kissed. His other hand was grabbing and rubbing my ass. The ferocity of the kiss and the foreplay was a complete turn on. My rock hard cock sprung out of my panties. I went down on him again as he fed his entire rock hard cock into my mouth and down my throat. I gagged as he held my head on his dick. I tried to come off it but he held me down causing me to gag again. My response was to dig my nails into his ass. He in turn ripped off my panties, fully exposing my hard on.

He pushed me down on the bed, my head on the pillow looking up at him. He inserted a finger and then second into my asshole. He spit on his fingers and then reinserted them. It didn’t take much for me to be incredibly wet and ready for his cock but his masterful finger play was a new sensation I really loved. He lifted one of my legs and slapped my ass as hard as it had ever been hit. As he repeated it again and again, I could feel a warming sensation on my left ass cheek and knew it was swelling. The pain was sensational.

I was so focused on the hard slaps that I had failed to recognize Sal's fingers were no longer inside me. I felt the tip of his dick start to push against me and then without much warning he thrust his entire cock inside me. I was so caught up in the burning sensation left by his hand prints on my ass I didn't immediately react to his cock completely filling me up. When I felt his body slap up against me and knew he was completely inside, a new feeling overwhelmed me. I could feel him swelling even larger than I thought he would be. I quickly realized that eight or nine inches may have been well over ten.

He started to fuck me, slowly at first, pulling his cock nearly all the way out before thrusting it back inside me. After a minute, the intensity of his thrusts picked up. He pinned my legs against my body giving him additional leverage to repeatedly slam his cock deeply inside of me. The sensation I felt throughout my body has never been duplicated. My body was paralyzed, moving only as his body thrust against mine. He held my legs together and toward my head with one hand and his other had made its way under my bra to pull on my very erect nipples. He would pinch them incredibly hard before pulling them. Every thrust became a little harder and deeper. My own cock was erect, pulsing and slapping against my stomach.

“Play with yourself while I fuck you!” he demanded.

I started jerking myself off to the same rhythm of his thrusts. It wasn’t long before I was coming all over myself. Sal rolled me over, fully mounting me from behind. My stomach was lying in a pool of my own cum. Our quiet but intense sex became loud and aggressive. I was screaming at him to fuck me harder, give me all his cock, and fill my pussy. He would yell back that I was a filthy whore, at times tightening his hands around my neck and throat or pushing my face down into the pillow, leaving me fighting for a breath and gasping for air when I could get free. It was the most intense sexual experience I've ever had.

I’m not sure how he was able to control himself for as long as he did. Nearly twenty minutes had passed since his first penetration, and I knew he was close. His hips were thrusting his cock harder and harder into me. Our flesh slapping against each other. My ass was burning. I yelled for him to fill me up with his cum. I wanted it all inside me. Moments later he exploded. His cock was buried so deep that I felt every stream of cum that left his cock shooting deep inside me. We lay there in silence for at least ten minutes. He started to speak but I stopped him. His cock was amazingly still very hard and still very much inside me. It was the first time I really thought about the sensation of giving myself up to a man and wanting his cum inside me. My mind fantasized about being impregnated by him. I was in unique space I had never been in before and I loved it.

I told him I wanted it again.

Rolling me over again on to my back, he pulled my feet up and reinserted his cock into my ass. It wasn’t long before he was swelling inside me again and we were back at it. The second time was even more aggressive than the first time. His massive cock was filling my sloppy cum drenched hole. He verbally became so demeaning, calling we a worthless slut and a fucking whore while he wrapped his hands around my neck and pushed down on my face with the palm of his hand. The ferocity of his slaps across both of my ass cheeks became violent. I could feel tears swelling in my eyes. He ravaged my cum drenched body. His thrusts against my ass and legs began to hurt. His muscular thighs were pounding against my body. I was begging him to shoot his cum inside me again which he did, much quicker the second time. As painful as it was, the pleasure was sensational. We kissed for a moment before we both passed out from exhaustion, his cock still buried inside me.

****

I woke up the next morning looking like a hot mess. My ass hurt like hell. My body had never been so sore from sex like it was that morning. Sal was awake and gone. I didn't even hear him get up. He had left a note for me by the coffee pot that simply said, “You are amazing. Thank you.” He had gone home to try and salvage his relationship with his girlfriend, an attempt he would admit was unsuccessful. We never had sex again and what happened that night was never discussed.

A few months later, we both graduated from college. The final month of school was depressing. I knew I could not bring my lifestyle home with me. I contemplated moving elsewhere but I knew I had to spend a little time at home to get things in order. I didn't have any kind of plan beyond some crappy guest services job at a hotel I was able to land. I packed up all of my clothes and donated them before my parents came up to see me graduate and help me move back home. I spent a lot of time contemplating my college years and my secret life I had led as Jenni. I didn't know what the future held and figured for now, it was so long my friend, until we meet again.