I met with Tabby on two other occasions after meeting her that night at the professor's. It was evident that after our third encounter that neither of us really knew where to take this relationship and mutually decided it was best to end our little fling. I was not heartbroken at all. I knew things would eventually run dry with her.

As winter came along, most of my weekends were spent alone. Sal and Sophie were typically homeward bound leaving me and my sexually perverse mind to wander. I often thought back to that first weekend after meeting Tabby. The self-suggested dare lingered in the back of my mind. I had slowly but surely started to stockpile items I felt were necessary for me to fulfill my fantasy. I had found andadult novelty store about thirty minutes from campus. The front of the store was primarily gag gifts and fifty-year-old birthday paraphernalia. The back of the store was a sex shop extraordinaire.

My first visit started with minimal makeup and no real visible female clothing. I felt the need to get a feel for the general acceptance of a crossdresser before walking in as a girl. Each visit I added another layer, a little more eye liner, a deeper shade of lip gloss, and slightly more feminine attire. Sometimes I would browse and other times I would make a purchase. I had added two dildos to my collection, both much more lifelike than what I owned, but it was when I purchased the third one that I had a breakthrough with the guy behind the counter.

“So, you’ve been coming here for almost three months now and I have to ask, are these for someone special or do you have some kind of dildo collection?” the clerk asked.

I laughed before answering. Figuring this was a guy who worked at a sex novelty shop asking me about the dildos I was buying. Why not be honest?

“If I consider myself special, and I do, then yes, they are for someone very special,” I said with a coy smile.

“That’s what I figured. My name is Mark, I’m actually the owner of this place.”

“Hi, Mark. I’m …”

While I figure the pause was far less than I imagined, I felt like I was silent for minutes.

“Did you forget your name?”

“No. I’m Jenni.”

“Well, Jenni, I think you and I both know that’s probably not your real name. I have watched you come in and out of my store for the last few months. You did not look like a Jenni when you first came in but you’re getting closer. Maybe if I told you you’re welcome to come in any time you would like, Jenni, that might make things easier for you.”

I felt relieved and let out a deep breath.

“Well thank you. I appreciate the offer. And yes, I think it would help me quite a bit.”

Mark and I had an enjoyable conversation and whether I wanted to hear it or not, I got the history of his life in what he called, the “adult toy” industry. He in turn, found out all about Jenni and eventually I let slip that I was looking for some information to help complete a dare that I had made to myself months before. Four months later, I was ready to try something I had never done before. Mark was ready to help.

I had become a little more withdrawn at the apartment and it was noticeable to Sal and Sophie. I was determined to slim up and worked hard to drop nearly twenty pounds. Each would frequently ask if everything was OK. I would politely say yes and that I was just stressed from school. The reality was that inside, I was never more alive. I would frequently pleasure myself with my collection of dildos and on occasion, would even use a fruit or vegetable as a suitable substitute.

My visits to the porn shop started to increase and with each visit my look became just a bit more risqué. Mark and I developed quite a friendship to the point where some nights I would just hang with him there, people watching, and shooting the shit for hours. It was never sexual with Mark. He was married to a woman named Kate who was of all things, a nurse. They seemed like an odd but really happy couple. And strangely enough, fully devout. Mark was great for always shooting straight with me when it came to my outfits. He knew what I wanted to do and was sometimes painfully truthful about my attire.

It was early March and while it was still relatively cold out, there were pockets of warm days that started to come around more frequently. One Friday night, I felt like it was the night to finally test myself and find out just how far I was willing to go to achieve my desire. Mark had convinced me that a certain short black mini dress, with a waist length leather jacket, and a pair of ankle high booties was the look I should go with. My makeup was so incredibly overdone and my hoop earrings big enough, my look could only be described as hooker-esque. And that was exactly the look I was trying to accomplish. I stopped at the porn shop to say hi to Mark.

“Holy fuck! Oh my god you look fucking hot! Incredible.” I got Mark’s stamp of approval.

Two college guys casually made their way to the front of the shop to see what all the fuss was about. They mulled their way around the shop glancing my way as they did.

“Can I help you guys with something?” I asked.

Red-faced embarrassed, they said no and quickly disappeared to the back of the shop again.

“You should go suck those two off before they jerk each other off,” he said loud enough so the boys would hear. “Please be careful out there. I can’t believe you want to do this. But god damn, you should be able to accomplish what you want pretty easily.”

After a little small talk, I was off. Mark had educated me on where to go downtown and certain boundaries I should not go past. I had driven through the area enough to have had everything planned out. Now it was about executing my plan.

Several months before, while I was feeling sorry for myself, I was convinced that I wanted, no, I needed to have sex with a stranger. I wanted to walk away from sex not caring if I ever saw that person again. I wanted cheap meaningless sex and where there was no relationship. I’d even just give a guy a blowjob. As long as there no “Can I call you?” after, I was good. I was tired of all the silly games being played. I just wanted sex. And I was going to do it in the most non-committal way possible, on the streets, with a stranger.

I had driven around the area I had targeted enough to know where to park and the general area that I would position myself. I took a few laps around the area and saw two girls who I had seen before. Otherwise, there wasn’t anyone else out on this weekday night. I parked my car in a nearby lot and started toward a particular corner that seemed far enough away from the regular girls but still in an area that would generate some traffic.

I realized as I walked, there was something about the sound of my heels on the sidewalk that completely turned me on. I was overly conscious about my walk, making sure it was both confident and feminine. I knew my legs were killer and my ass looked perfect, peeking out from underneath my jacket. My heart was absolutely racing. I had only walked two blocks, but it seemed like ten by the time I finally reached the spot I was calling my starting point.

I started conservatively standing near a building on a street corner. After getting my bearings, I decided I would walk around a little, staying well within my designated circle. As car after car passed, I realized that most were checking me out and that turning a trick was far more difficult than I imagined. After about twenty minutes, I slowed my stride and started to feel a groove. I would start and stop walking with the flow of traffic. Even if I did not find anyone, I was out on the street, dressed like a slut for the world to see. I felt incredible and very alive.

About two hours in, two cars had stopped to talk to me. One guy wanted to sell me crack and the second was a guy who just wanted to tell me that I was an ugly whore before speeding off. I kept an eye on a clock that was displayed on a bank sign as I walked. I watched it slowly get later and later. I swore I would stop playing hooker by midnight, but the clock told me it was well after midnight, and I was in no hurry to go home. I ran into a girl who introduced herself as Amber. She did not look much an Amber but who was I to judge. We talked for a few minutes until a car pulled up alongside of us and rolled the window down. Amber walked toward car, and I started to walk away.

“Honey, this one is for you if you want it,” she said.

I stopped and turned back to see a normal looking guy driving a normal looking car. This is what I was there for, right? For some reason I wanted to walk the streets and prostitute myself out to a stranger. Why? I really wasn’t sure but there I was, and it was now or never. I walked back toward the car, my heart rate picking up as I approached Amber and the car.

“Girl, he’s kind of cute if you ask me. He’s got cash and condoms too, if you want.”

“Thanks Amber, what more could I want?” I asked as I leaned over and looked in. He was a professional looking guy, maybe in his thirties. He wasn’t what I would call hot but very normal looking.

“So, what are you looking for tonight sweetie?”

“I really just want my cock sucked and I’ll pay you one hundred to do it,” he said in a very nervous almost shaking voice.

I hadn’t even thought about the money part of things. He was going to pay me to suck his cock. This was great.

“You ain’t a cop, are you?” I asked, figuring it was a fair question to ask.

“No. I just want a blowjob from a hooker like you.”

“OK honey, you want to go somewhere to do this? What did you have in mind?”

“You’re call. But private.”

“OK. How about that parking garage across the street?”

“That will work. Do you want a ride or are you going to walk?” His awkwardness was amusingly delightful.

“You can drive me, if you don’t mind.” The lock popped up on the passenger side door and I climbed in.

“Suck it good, baby girl,” called Amber as I pulled the door shut and blew her a kiss.

There I was, in the front seat of a stranger’s car, driving to a parking garage to give him a blowjob for cash. I was mind blown, my heart was racing, and I was really fucking horny. I thought to myself, please let him have a nice cock. My night would be so complete.

“So have you done this before?” I asked as if this was second nature to me. I figured that would be a good question to lead off with to see who I was dealing with.

“No, I haven’t. My girlfriend just broke up with me and my revenge on her is getting a blowjob from a hooker. Are you OK with that? And can we not talk about it?”

“I’m all good sweetheart. I can definitely help you out,” I replied as he turned left into the parking garage. “Go to the third floor,” I said, sounding like an old pro. He did as he was told.

“When we get up there, park anywhere you want and put the money right in between the seats. Whatever you do, don’t hand it to me directly.”

Why? I have no idea, but it sounded like the kind of thing a hooker would say. He parked the car and did as I asked. He placed down what appeared to be five twenty-dollar bills that I picked up and put in my purse.

“Front seat or back? Which would you prefer?” I asked.

“Let’s do it right here. I’m sorry I’m so nervous and jumpy. I have never done this before and I’m mad and nervous.”

I put my index finger to his lips and gave him a “shhhh.” My other hand reached between his legs and felt his cock which I could see getting hard as we were pulling in. I repositioned myself in the passenger’s seat and told him to pull his sweatpants down. His cock was nice. It was about six inches and perfectly erect. The shaft was undersized in its thickness compared to the head which was very large.

“Take a deep breath and enjoy. She was a bitch for leaving you,” I said as I lowered my lips down on to his cock. I slowly moved my lips past his head and slowly took inch by inch until he had filled my mouth and throat. He moaned as I let my tongue run circles the shaft a few times before slowly withdrawing.

“How does that feel?” I asked.

“Perfect,” he replied.

I took his cock in my mouth again, slowly starting to move my lips up and down his shaft. I attached my lips and made my way back to his monster head, licking it and gently kissing the very tip. My hands cupped his balls as I licked downward, eventually taking one and then the second ball in my mouth. I stroked his cock slowly as I sucked on his sac, his balls quivering in my mouth as I did. He leaned his seat back allowing me a little more room. I slowly sucked his dick, in no hurry to have him cum. I looked up to see his eyes closed and his right hand squeezing the arm rest. I enjoyed his cock for about ten minutes, slowly building him toward cumming before easing back to lick his balls or kiss him around his cock.

Figuring he couldn’t hold up much longer, I took all of his cock in my mouth and started sucking up and down at slightly more rapid pace. I could feel him start to swell a little more, his balls shaking as I fondled each of them.

“Oh god, I’m going to cum,” was about all the warning I got before stream after stream of sweet cum shot into my mouth and down my throat. I swallowed the first load quickly and as I did, I could feel him shooting more cum into my mouth. This guy had quite a load. It tasted fantastic. I licked up and down his shaft while gently stroking him, trying to get one last taste as I did. I kept licking and played with his balls for a moment, sucking on each of them one last time before licking back to his head, kissing his tip oh so softly, and licking up the last drop. I gently pulled his sweatpants up over his now limp dick. I sat back down, adjusting my dress, wiped a little cum off my cheek and touched up my lips.

“I hope you enjoyed that. You were delicious.”

“Oh my god that was amazing. Way better than my wife when she gives me head.”

“Get the fuck out of here. What was with the bullshit about the girlfriend breaking up with you? You should have just told me you were cheating on your wife, and I would have let you fuck me for the same hundred,” I said laughing.

“No way?! I have another hundred.”

“No way, now it's two hundred and I want it in my ass.” His eyes grew big, and I could tell he was excited. “But not tonight sweetie. I gotta get back on the street.”

“Yeah, that’s cool. Anyway, I have to get back home. Can’t keep a pregnant woman waiting.”

“So, your pregnant wife is at home and you’re out getting your cock sucked by some girl off the street?”

“Please don’t judge,” he started to respond before I cut him off.

“Judge you? Sweetie, I’m out on the streets sucking dicks for cash. Who am I to judge? Just be kind enough to drive me back down to my corner if you would.”

“Can I really fuck you in the ass for two hundred dollars though?”

“Why don’t you bring your money and those condoms next week, same time, and we’ll see what we can do.”

He seemed thrilled at the prospect of having anal sex with me, telling me his wife hated it in the ass. He drove me back down, thanked me as I climbed out of his car, and drove off as soon as the door shut. I took a deep breath and figured I’d walk back to my car and head home. I had accomplished what I had set out to do, the only problem was that I liked it. No, I loved it. There was a thrill, an excitement in being out on the street, completely vulnerable, and out on display. I was being paid for sex. I was a half block away from where I had parked and decided that even though it was after 1am, I would make one more pass around the block and look for Amber. I was hoping for someone else to stop me but after another twenty minutes of walking and no takers, I headed to my car to go home.

As tempted as I was to stop by the sex shop and share my experience with Mark, I was exhausted. Turning tricks was a lot harder than it looked. I realized playing it safe probably made it a little more difficult. Blocks from where I was at, there was a much heavier presence of girls, drugs, and police. I chose to steer clear for my first night out. By the time I got home, my feeling of exhaustion gave way to an incredible wave of horniness. I did a shot and climbed into bed with one of my favorite toys to pleasure myself. Would there be another night on the street? Only time would tell.