Uber Tales - Bachelorette Party

I want to thank Nthusiastically for her help editing this for me. Much appreciated!

*****

"Harder!" she shouted. "Faster!"

I wanted to give her exactly what she wanted, so I increased my effort. She was bent over the back of the car, her hands on the trunk, as I pounded her from behind.

How did we get here? A nameless girl on the side of a nameless road. And why are we both naked? There were questions, too many to dwell on, so I let them pass by unanswered. Instead, I just kept on pumping into her, feeling that pressure build up until I couldn't hold back any longer. One final deep thrust into her and...

I woke up.

As was the case with all of my erotic dreams, I woke right before reaching my climax. Just in case it was different this time, I checked the sheets to make sure I hadn't left a deposit. In my pubescent wet dreams I would cum in my dreams and awaken to find that I had actually spilled my seed. Since then I've somehow trained myself to wake up before I climaxed to avoid messy sheets. No, nothing there this time except a few drops of pre-cum on the head of my rock hard member. There would be no sleep for me until I took care of that, so I did what I had to do. I closed my eyes and tried to get back into that dream. Spreading the pre-cum over my shaft, I took a couple of hard and deep thrusts into her. That was all it took. Bedside Kleenex and all is well.

As I dozed back off I thought more about the specifics of the dream, but as is the case with dreams, the details got fuzzier with time. While I didn't know the name of the woman or the location of the roadside activity, I knew why I kept revisiting the dream. It started three weeks ago...

I drive for a ride-sharing company. I live in New York City, in Brooklyn, outside of Manhattan. While many of my rides stay on Long Island, a good number of them lead me into the city, especially on weekends.

This weekend was no different. It was late on a Saturday night. I had been driving since early afternoon and had already decided that the next pick up, if it had me heading back towards home, would be my last of the day.

The request came in to pick up 'Sue +3', Sue and three other riders. Four riders were the maximum my car could hold, so it would be tight with one rider in the front and three in the back, but increasing the riders also increased the chance of getting a tip. I was familiar with the location for the pickup, which was at a club in midtown, so I didn't need the navigation app. As I pulled up to the curb outside the club, a woman waved at me. I rolled down the window. "Are you Sue?" I asked, to confirm the pickup. "No, 'she replied, "I'm Cindy. I'll go get the rest of the group. Be right back." And she disappeared back into the club.

I've been in this situation before. "Be right back" can be a matter of minutes or much longer. I learned that I could turn on the ride once I made contact with the rider, so I did. There were multiple drop-offs, but the first was in Brooklyn, so I was going to be headed towards home. So far so good.

Cindy came back outside with three other women in tow. All four were attractive and were dressed for a night out on the town; with low-cut tops and short skirts, there was plenty of skin showing. I'd guess that they were all in their early 20's except Cindy, who looked to be a little older, perhaps in her late 20's pushing 30.

I got out of the car and held the back door open. Three of the women climbed in, and by the lack of grace in which they did, I sensed that they probably had more than their share of alcohol over the evening. I internally repeated my late night mantra: 'Please don't be sick in the car...Please don't be sick in the car'. It's happened before and it was not an experience that I wanted to repeat.

Cindy was left at the curb, so I walked around to the passenger side and opened the front door for her. Unlike the other women, she entered gracefully, with her short skirt showing a good portion of her thighs. I got the feeling that she was the more responsible party in the group, perhaps the 'designated driver' per se.

Getting back into the car I introduced myself and got their names back, albeit a bit slurred and with lots of giggling. The only name that I was sure that I caught was Sue, sitting between who might have been Tori, or perhaps Tammy or Toni, and Debbie, or perhaps Betty. I locked the first drop off location into the navigator and headed out of the city.

Sue and her backseat friends kept up the giggling and talking. I've found that people feel they can say anything in front of a car driver, or cabbie. I guess that it's similar to people feeling free to discuss anything with their hairdresser or bartender. The talk among the three in the backseat let me know that they had just left a bachelorette party. A male stripper was the entertainment, which was a surprise that Sue seemed to have organized.

"He had to be the hottest guy in the world!" exclaimed Debbie/Betty.

Tori/Tammy/Toni added, "He totally filled up his banana hammock!"

"His hammock overflowed (giggle)."

"Thank God you had the nerve to release him". Apparently, Sue had taken the initiative of revealing his cock.

The talk continued in the backseat, although in the front seat Cindy wasn't joining in. I caught fragments of their conversation; "That had to be the biggest dick I ever saw - at least in real life", "I couldn't get my hand around it", and "It kept getting harder - and bigger." From what I gathered Sue had not only been the instigator of the entertainment, but she was the one that kept taking it up a notch. She was the first to touch him once she removed his hammock, the one that supplied the can of whipped cream, and the first one to lick some of it off of him.

"That was definitely the biggest cock I've ever had in my mouth," she said. "I'd have liked to see if it could fit elsewhere."

When she said that I caught a glimpse of her in my rear view mirror. She was looking back directly at me with an almost evil grin. I broke contact and glanced over to Cindy. She looked over at me; she seemed to be a bit horrified and a bit apologetic. I returned a look of 'whatever' and shrugged my shoulders.

The conversation and giggles continued until I was at the first drop off spot. It was Tori/Tammy/Toni's and Debbie/Betty's and at an apartment complex; they either lived together or were having a sleepover. I helped them out of the car as it could have taken them a while longer to get out on their own accord. I got an eyeful of Tori's breasts as she leaned over a bit too far. She was very well endowed and they almost escaped her blouse. I also got a handful of Debbie's ass as she fell against me trying to stand up. She giggled; apparently, she was the main source of all that giggling. With one on each side of me, I helped them up the steps to their apartment and made sure they could get it unlocked. Once inside they were on their own.

Back in the car, I entered the next drop off location into the navigator. It was for Sue and showed as being a 10-minute drive.

The noise level in the car decreased dramatically; at the very least the giggling was over. But Sue wasn't finished describing her evening.

"Seriously, it was the biggest..." She paused. I looked at her in the mirror and saw she was once again staring at me. "The biggest COCK I've ever seen." She exaggerated 'cock' for effect, looking to see how I'd react. Turning towards Cindy she continued "And I can't believe you wouldn't even touch it."

Without turning around, Cindy responded to Sue, talking straight ahead. "I told you there were too many cell phones snapping pics. I can't afford to have pictures like that hit the web. And besides, I did touch him."

"As I recall, just once," Sue said. "And he was still in that ridiculously tight banana hammock. You also missed out by not tasting some of that whipped cream. Soooo delicious!"

Cindy replied to that with "I don't like whipped cream." Her tone implied, at least to me, that that was the end of that conversation. Sue didn't pick up on that and added a final remark. "Your loss."

There was a lot of tension in the car from then on, and less conversation. I actually thought Sue might have dozed off a bit as I lost sight of her in the mirror for a while. But when I pulled over at her stop she was wide awake, waiting for me to give her a hand out of the backseat. Following Tori's lead earlier, she leaned far forward, making sure I got an eyeful of her breasts. One slipped totally out of its confines. "Ooopsie!" Sue said, and after she was sure that I got a chance to check it out, she made a show of slowly tucking it back in. And as she slid out of the seat she somehow arranged it so that her already short skirt got hiked up a bit. I couldn't be sure, but I think she was going commando.

She turned towards Cindy in the front seat and said: "Don't forget to leave the gentleman a nice tip!"

One thing I was sure of, as I helped her walk up the steps to her house, was that I could have had my way with her. She had her hands all over me, grabbing my ass on the pretense of falling down, putting her arm around me for support and then grabbing my thigh. My guess was that she was horny from the evening's activities and wanted to be fucked. And under other circumstances, I might have done just that. But she was pretty drunk; if she was sober, the outcome might have been different.

Back in the car, I updated the navigation app to see where Cindy's drop off was. It said she was 35 minutes away.

I thought of two things. One - I was going to make a nice chunk of change from this already long ride. And two - that I felt a little bit sorry for Cindy in the way that her 'friends' had treated her.

She spoke first. "I'm sorry for Sue. She's pretty much always like that - not the shy one at all - but after a few drinks she's totally off the wall."

"It's ok. I could tell they were all pretty hammered." I said. "But you... not so much?"

"I've had more than my share, but, yeah, I guess I'm the 'responsible' one in the group."

"I guess you didn't have a good time," I said.

"I take it that male strippers aren't really your choice of entertainment."

She laughed. "Actually I enjoyed the show. And Sue was right; he was hung like a horse!" She looked over at me and smiled. "And I did want to touch him, but I really worried about the cell phones." She explained that she had just finalized her divorce and was still on edge about being seen out and about. Also, she had a teaching position at the local community college and if pics got out it could be a bit of a mess.

"Would it make you feel any better if I told you that most likely the guy was gay?" I said. "From what I hear many of them are."

She laughed then said "Well, that could explain why it took him so long to get excited. I would have thought that with all those women touching him he would have gotten hard pretty quickly, but it took a while."

"It could also be that he was a 'professional' and had a lot of self-control," I said which got another laugh from Cindy. "I'm not a professional; I know I'd have issues right away."

I was enjoying driving Cindy. She had a very easy relaxed attitude and I found it interesting that we were able to talk openly about, well, to talk openly about strippers and cocks and erections. I had originally pegged her as being shy, but now that it was just the two of us I realized I was probably wrong about that.

I offered to turn off the Uber app for the rest of the ride; a freebie because I was enjoying the conversation and because it was my last ride of a long day. Cindy told me not to because Sue is paying for it and 'she can afford it'. Also if Sue looked into the billing she might question why the ride ended short of the final destination, her house.

I said, "I take it that Sue was pretty proud of herself for taking the initiative tonight."

Cindy replied, "Yeah; not exactly anything to be proud of."

She continued. "I actually would have liked to participate in the action. I think they thought I was being a prude, but I had my reasons for abstaining. If they only knew."

There was a moment of silence, as I didn't know how to respond. Then, before I could think of something clever to say, she asked if I could do her a favor. I said "Possibly. What is it?"

Again there was a moment of silence from her. I sensed she was hesitant; undecided if she wanted to ask the favor. I tried to ease it from her. "It's ok to ask. I'll answer honestly, one way or the other."

Cindy looked over at me and blurted it out. "Can you be my stripper?"

I was shocked and again I didn't know how to respond. I realized that I had been wrong in my evaluation of her. She might have been shy at first, perhaps hesitant, but now she was definitely asserting herself. Perhaps that was because she hadn't asserted herself earlier in the evening.

Before I could think of anything to say she reached over and put her hand on my thigh. She said "I have to let you know that I lied earlier to Sue, just to shut her up. I actually do like whipped cream; I love whipped cream!" And then she asked again "Will you be my stripper tonight?

I understood what she was asking. I felt like I had to put up at least a mild protest, though truth be told I was warming pretty quickly to the idea. I told her "I'm not a stripper and not even close to stripper material." Cindy moved her hand further up my thigh, cupping my crotch, and said: "I bet you'll be just fine." It's hard to argue with a woman when she's got your balls in her hand. Smiling, I said "OK - I'll give it a try." She returned my smile.

She dropped her hand back down to my thigh as I continued to drive. We were already in her neighborhood; the app actually said we had arrived. Cindy reached into her purse and came out with the garage door remote. I saw the house ahead and turned into the driveway just as the garage door was opening. And as soon as I had pulled all the way in, Cindy hit the remote again to close the door behind us. I turned the app off, finishing the ride, and Cindy led the way into her house.

We stopped in the living room. I took in the décor; based on what was in the house, as well as the size of the house and the neighborhood we were in, I had to assume that either she or her husband, or both, had money. She noticed me looking around. "He doesn't live here any longer. I assume that he's shacking up with his secretary. How much of a cliché is that?"

I didn't respond, just turned toward her and asked: "So, how does this work?"

Cindy laughed and said "I guess I haven't really thought it through. I'm going to make myself a drink. Would you like one?"

I sounded like a good start. 'Sure, I could use a stiff one. I have some catching up to do."

My choice of words was unintentional but Cindy picked up on it. She glanced down at my crotch "OK, I'll see if I can get you a stiff one."

She continued. "The CD player is behind the cabinet over there." pointing to the corner. "Why don't you pick out some music?" She went into the kitchen and I went over to check out her selection of music.

I didn't see anything labeled 'Music to strip to', but I found a CD of jazz ballads. I enjoy jazz, so if nothing else it might help me to relax.

Cindy came back with a scotch for me and white wine for her. I downed mine quickly.

She walked closer and unbuttoned my shirt, then sat down in the closest chair and said "There. I got you started. Go on.."

I started swaying a bit to the music. I'm not much of a dancer so I tried not to imagine what I looked like. I was just trying to get into it, slowly removing my shirt. Once off I threw it towards Cindy. She shouted "Bravo!", then motioned me back towards her. As I stood in front of her she ran her hands up my legs, over my crotch, until she got to my belt. She undid it, unsnapped my jeans, and pulled down the zipper. "Ok, back in your hands," she said, motioning me back away from her.

I backed away and tried to be seductive as I lowered my pants. I was wearing boxer briefs, which are my underwear of choice but admittingly not the sexiest. I doubt that I had succeeded in being seductive but I was far along on the way to an erection, so I was showing pretty well.

Cindy eyed me over, from top to bottom, with her gaze ending at my crotch. I slowly turned around to give her a view of my ass. As I had told her I was definitely not 'stripper material', but I did occasionally work out and had some muscle definition. I wasn't ashamed of my body and at the moment I was far past any pretense of being shy. Cindy said "Mmm", then reached over to her purse and pulled out her cell phone. "I'd like to preserve the moment. Is that OK?" Considering that photo taking was one of the things that turned her off to getting touchy-feely with the stripper, I was a little surprised at her question. "No face shots - I promise" she added. "And you can go through the pics and delete any that you want."

I said OK and Cindy started taking some pics.

Then she motioned me over to her. Setting the camera aside for a moment she put her hands on my hips and hooked her thumbs under the waistband of my underwear. She looked up into my eyes and with a devilish grin slowly started to pull my shorts briefs down.

My dick, while not fully erect, was far from flaccid. I keep myself pretty well groomed and was glad that I had manscaped just a couple of days ago. I had shaved my balls and around the base of my cock, leaving just a small patch of closely cropped pubes.

Cindy must have approved. She cheered "Yeah!" and applauded, then picked her phone back up. She took a couple of pics then touched me for the first time as she took a pic of her hand around by shaft. Her soft hand immediately caused a reaction from me; my cock started to expand. Cindy smiled and said, "You know that's very unprofessional, right?" I smiled back and replied, "You can't say I didn't warn you.."

She said "Hold that pose... I'll be right back."

She hopped up from her chair and left the room. True to her word she quickly returned, obviously holding something behind her back.

She returned to her chair and said "I do indeed love whipped cream," and showed me a can of Reddi Whip. This was getting very interesting.

When I'm fully erect my penis has a distinct bend upwards and it was rapidly reaching that point. "So unprofessional.." she repeated with a smile.

She reached for me, and, holding my shaft down so that it was level, sprayed a dollop of the whipped cream right on the tip. The blast of cold caused my cock to jerk a bit, but she held it firmly down. Switching the can for her cell she took a couple of pics of my 'tasty' cock. She seemed intent on documenting this entire encounter.

Cindy put the cell down and said "Mmmm. I think we're both going to like this." She moved her head closer to me and stuck out her tongue. Before she made contact with the whipped cream, I stopped her and aid 'Hand me the camera. I have a good view from up here." She smiled and handed it to me. She stuck her tongue back out and started to lick the whipped cream off of me as I took some pics. Somehow she managed to get most of the whipped with very little contact. I wasn't going to settle for that so I reached down and took the can. I moved her hand off of me and let my hard cock spring back towards my belly, then sprayed a hefty line of whipped cream on the underside, from the tip down to my balls. She smiled, and without a word started licking it up. She started at the base and with each lick, my cock jerked a bit more. By now I was fully erect and as hard as I can ever remember being. As she took her time working her way up my shaft, I was a bit concerned that I might explode before she finished. I held off and eventually she licked all of it off of me as I continued to take pics.