Good girl in stripper heels. [M/F] | 2016

My sessions with Chloe ultimately ended after about a year. She was an amazing sexual partner and exactly what I needed at that point in my life. But as I put some distance between me and my ex and I started dating again, going to see Chloe wasn't the necessity it once was.

After being single for a couple of years and a career change that saw me working normal hours, I dated a coworker for the better part of six months.

Andi was slim with a small waist and a little ass, and was maybe a small B cup. 23 years old. She stood 5' 2" and was very cute and sweet. Maybe 110lbs. Had a bit of an Amy Smart vibe about her.

If I've got a type, it would be trashy women. Tight clothes, fake tan, overly elaborate hair. Andi didn't fit this mold. She was a small town girl that had recently moved to the city and while she'd had boyfriends, I got the impression they were the under the covers with the lights off kind of guys. It wasn't like she wasn't a fun, willing partner. She was just inexperienced.

It makes me sound like a jerk but she was more into me than I was into her. I was genuinely fond of her but in my mind, I didn't have any long-term interest. I treated her very well, though. I got the impression that I was her first boyfriend that was considerate and was concerned about her needs (emotional and physical). I think she trusted me and felt safe with me and this made her more open to experimentation.

We'd been dating for a few months when I suddenly came into some money. I asked Andi if she wanted to go to Vegas with me and she jumped at the offer. She'd never been but had long wanted to go.

I'm a fan of going to Vegas mid-week because it feels like it's less busy and the hotels and casinos have more time for me. We'd been in town a couple of days when I offered to take Andi shopping.

There used to be a place not far off the Strip that sold shoes to strippers. It might still be there. I'd been to Vegas a number of times before and the store was a hit with whoever I was with at the time. This wasn't any different. Andi tried on an unending assortment of shoes and, after some convincing from the sales girl, took a spin around the stripper pole that was in the store. In the end, she settled on a pair of black heels with just a bit of a stripper platform to them. What she really liked, though, were the long straps that wrapped around her calves again and again. She had great legs and they looked amazing in the shoes.

Across the street was some kind of cheap clothing store with knockoffs of brand names. Of all things, I needed a pair of socks so we ducked in there real quick.

I grabbed what I needed but had to go looking for Andi. She was looking longingly at a black dress with red trim and a matching red flower on it. I told her to go and try it on.

She came out of the dressing room smiling and excited. She looked great. Again, my prerequisite for a dress is tight and short and while this didn't tick those boxes, it was sexy. Modest by Vegas standards, it was a departure for Andi. I bought it along with my socks and we went back to the hotel to lay around the pool and do a little gambling.

We had a late lunch and I told Andi I had plans for us that night but wouldn't say what. We went back to the room to get dressed and Andy put on her new outfit while I put on a suit.

Andi had never been to a strip club and I thought Vegas was the place to rectify that. Without giving her a hint, we went to a nearby club called Treasures. It used to be if you called the club, they'd send a limo for you. The car was waiting for us outside our hotel and dropped us right in front of the club.

She was really shy when we first walked in but that wore off after a few drinks. Her cheeks were flushed and she laughed non-stop when I bought her a lap dance. She watched as I got one next. At first she watched the girl gyrate on my lap but soon she instead started watching me. We held each other's gaze and Andi started rubbing the inside of her thighs near her knees and I knew it was time to go.

Outside in the parking lot, Andi was pleasing tipsy and I had a buzz going too. A girl on her way into the bar told Andi her shoes looked hot. This gave Andi a big ego boost. The limo was gone (presumably picking up more customers) so we took a cab back to the hotel instead.

Andi was giggly and laughing when we got into the taxi. "That was fun!" she kept saying too loudly. I put my hand on her leg and started moving it north. She spread her legs just a bit and got quiet and bit her lip. I could see the cab driver sneaking peeks in the mirror.

"What are you doing?" she teased.

"Whatever you want," I breathed in her ear.

She shook her head. "Whatever YOU want," she said.

I've learned to jump on those opportunities when presented. "Take off your panties," I said.

"When?" she asked, a little confused.

"Now," I said.

She hesitated. She wanted to please me but was shy. "He'll see," she said, referring to the cab driver.

I caught him watching in the mirror and told Andi he was too busy driving to pay attention to us. Taking the hint, he suddenly hit the horn and started swearing at an imaginary incident in front of him.

Andi bashfully wiggled her panties off her hips. I could see she was a little wild eyed, worried that the driver would say something. When she got them as low as she could get them without pulling them past the hem of her dress, she asked, "What now?"

"Take them off and give them to me," I instructed.

She paused to gather her courage and then tried to kick them off in one smooth motion but they got caught up in her new shoes' straps. In a little bit of a panic, she finally got them off and then tried to nonchalantly pass them to me. It was a little, black, lacy thong. I could feel they were damp as I put them in my jacket pocket.

I moved in to kiss her neck and snaked my hand up between her legs. Her pussy was shaved bare. "You're nice and smooth," I muttered to her. She just moaned and held my hand between her legs through her skirt. I teased her, gently petting her without giving her any direct stimulation.

Arriving at the hotel, she made an effort not to flash everyone waiting for a ride when she stepped out. I paid the cabbie and he told me to have fun.

Hanging off each other, we zigzagged through the casino to the elevators that would take us to our room. The elevator arrived and we got on. We had it to ourselves.

The inside of the elevator car was mirrored. I stood behind Andy and wrapped an arm around her. We looked at each other in the mirror. I kissed her neck while my free my hand dropped to her dress and I started to slowly hike it up. She didn't notice what I was doing until she was exposed and when she did notice, she didn't care. "I'm so horny," she said and started to absentmindedly touch herself. We didn't realize we were at our floor until the car stopped and the door opened. There was no one else in the hallway as we hurried to our room, grabbing and groping each other.

We barely made it inside the room before we were shucking off our clothes. Andi stepped out of her dress but I stopped her when she started to take off her shoes. She jumped at me and helped speed up the removal of my suit.

Still groping each other in the doorway, Andi said she liked the mirror in the elevator and wished we had one over the bed. Making do with what we had, I took her into the washroom and bent her over up against sink so that she was only inches away from her reflection. I also had her put one leg up on the counter so her pussy and asks were fully exposed.

I got down on my knees and ate her from behind. I gave her pussy my full attention, only using my mouth. Eventually, I started licking her asshole while pushing a finger into her box and rubbing her g-spot. Andi loved having her ass eaten and she was a squirter but I don't think we'd ever tackled both simultaneously.

Her hips were grinding air and the leg she was standing on started to tremble. I slid a single finger into her little ass while still fingering her cunt and she went into hysterics, moaning and gasping and squirting on the gaudy marble floor in the bathroom. Trembling, she turned and sat on the counter, leaning back against the mirror her face was just pressed up against.

"Did you like that?" I asked, full well knowing the answer. She nodded yes. "Want to try something bigger back there?" I wanted to know.

She paused before answering yes. I could see she was nervous and I promised we could stop any time.

I got my shaving bag and dug out a small bottle of Astroglide and proceeded to grease up my cock along with her asshole. She loved watching me stroke myself and starred contentedly until I pressed my head to her backdoor.

"Ready?" I asked. Still looking down, she nodded and I started to push myself into her. She'd make an involuntary gasp or whimper and I'd pause, letting her adjust to the sensation.

"Ever done this before?" I wanted to know.

"No," she admitted. "It hurts a little but don't stop."

We eventually worked our way up to lazy thrusting. She had both hands around my neck and our foreheads were touching. Her mouth open and her breathing shallow, she whispered that she wanted to ride me.

I sat on the closed toilet and waited for her to join me. She was setting the pace. She took the lube from the counter and slathered more on my cock. "I can't believe what you're doing to me," she said softly before turning around and sitting back down on me. She still went slow but it was quicker than when we started.

"You like it, don't you?" I wanted to know.

"Yes," she admitted. I couldn't see but knew she was rubbing herself.

"Put two fingers inside yourself."

"This is so dirty," she said before putting her fingers in her pussy as instructed. "I can feel you with my fingers," she said in amazement. She started riding faster and pushed her fingers in deeper. I knew she was going to cum. "Be loud baby. Wake up the neighbors," I whispered in her ear.

With that little bit of encouragement, she started moaning loudly. There wasn't any dirty talk but she was making guttural, primal noises. There was no doubt anyone in the hallway would be able to hear her.

I was at my limit."Can I cum in your ass, baby?" I asked. She nodded yes so I grabbed her lithe hips and pulled her down onto my hardness as I fired rope after rope of jism up her ass. We sat there in the afterglow for a moment before she stood up. A great glob of sperm fell out of her and onto the floor. She took me by the hand and lead me to bed where we collapsed in a sweaty, intertwined mess.

"I love you," she said just before dozing off. I answered by kissing her forehead. She fell asleep still wearing her stripper shoes.