I moved to a new city for a new job about a month ago. All I’d done in that month is get settled into a new apartment, and work. I was single, reasonably attractive, not completely without charm, and I now had a pretty good job; but I was having no luck finding women to go out with me. I had broken up with my previous girlfriend because she hadn’t wanted to move with me when I had gotten my new job. No, career. If I played my cards right, this was going to be my forever job. Like most people in their 30s, I’d had a variety of jobs since getting out of school. So when I had landed this opportunity, I had been thrilled.
However, I didn’t have any friends yet in my new city. I mostly worked with older people that had kids and families. Someday that may have been in my future, but not right now. I had been tempted to try online dating, but that seemed daunting. I had met my last girlfriend at work, and we’d been together for four months before we had broken up. I hadn’t been on any dates since.
One Friday night after work, I decided to hit up one of the local bars near my apartment. I had tried to talk to a few women, or buy them drinks, but they were all in groups, or had boyfriends. After about an hour of listening to the cover band, and three beers later, I decided to call it a night. While I was driving home, a neon sign caught my eye. All it said was “Gentleman’s Club.”
It was in front of a squat gray brick building with no frills or decorations. I shrugged and pulled into the parking lot. I figured “what the hell, at least I can see some tits before going home.”
I went inside, paid the cover and sat at a booth alone. It was a pretty dingy place, and not very crowded, even for a Friday night. A waitress wearing only black panties, high heels and pasties on perky tits came over and took my drink order. There was a large stage in the middle of the room with a busty young black girl dancing on a pole, and two smaller stages next to it. Each one had a dancer performing for a small group of guys. Most of the dancers were probably in their 20s or 30s. Some were walking around looking for any customers that wanted a private dance. Occasionally, a dancer would take a guy’s hand and lead them to another room behind a curtain for private dances. I was looking at the curtain when the server brought me my drink, I tipped her $5 and went back to watching the show.
After a few minutes, a petite Asian girl came over and asked if I wanted a private dance. I hadn’t even been there ten minutes, so I declined and told her to check back after a little while. I watched a couple more dances on the main stage and tipped the performers each time they came by. I noticed on one of the side stages, there was an older performer. She was easily the oldest stripper in the club, but not unattractive. She was white, probably 5′ 6″, had dark black hair and was currently taking her clothes off a piece at a time. She had huge boobs. Easily DD or larger. Large areola and semi-hard nipples. Thick thighs, and extra pounds around her stomach and ass. Not fat, but definitely not skin and bones like some of the other dancers. After she was finished dancing the MC announced that her name was Midnight. I was going to tip her because I thought she had danced well, and I she was more my type, but she didn’t come by my booth.
I watched the show some more, and noticed Midnight approach a group of young guys, probably all in college. I could tell she was asking if any of them wanted a private show, but they all shook their heads. I saw the look of disappointment when she turned away. Same thing happened at the next table. And the next. She looked around, spotted me alone, and started walking over.
When she got to my table she smiled and said “hey there, enjoying the show?”
I said “I am, it’s my first time here. Would you like to sit down?”
She nodded and sat down across from me and said “thanks, my feet are killing me in these shoes.”
I said “they don’t look very comfortable.”
She laughed and said “I don’t wear them for comfort. They make my legs look good though. I’m Midnight.”
She was right, the shoes made her legs look nice. I said “I’m Will. How’s your night going?”
Her smile dimmed a little and she said “not great. It’s a slow night and I’m making crap for tips. And no one wants a dance from someone old enough to be their mother. Young customers tonight. There’s usually a few older regulars that don’t mind, uh, experience.”
I asked “how much are the private dances?”
Her smile perked up and she said “$100 for topless. $150 for fully nude. Would you like a dance? I need to make about $250 tonight to cover my rent and you’d really be doing me a favor if you said yes.”
I smiled and said “I tell you what, I’ll give you $250 for a long dance if you tell me your real name.”
She laughed and her blue eyes twinkled when she said “what? You don’t think it’s really Midnight?”
I grinned and shook my head.
She smiled too and replied “it’s Stephanie. Let’s go.”
She took my hand and led me to the curtained area and we entered a dimly lit room that had a comfy couch in it. When we walked in, the loud music from outside was muffled. I took the cash from my pocket, counted out $250, and handed it to her.
She put it in a small purse I hadn’t noticed before and said “thank you. You’re a life saver. Want me to get started?”
I said “before you do, can we talk for a few minutes? I’m new to town and haven’t really met anyone.”
Stephanie sat next to me and said “I’d love to, most guys barely even look at my face in here. All they care about is seeing my tits and pussy.”
I chuckled and said “I want to see those too, but I can wait a few. Have you been dancing long?”
She replied “on and off for about 20ish years. When I was younger, I’d make $5-600 a night easy. Now that I’m old though, half that is a good night.”
I said “I don’t think you’re old. And I think you’re hot as hell. Big chest, backside, and pretty eyes. What else could I want?”
She smiled and said “you’re sweet for saying that, but most guys seem to like fake tits rather than my natural girls.”
She shook her chest and asked if I was ready for her to start. I nodded and she said “no touching, club rules.”
I told her that I understood and laid my hands on the couch cushions next to me. Stephanie went over to a sound system and turned on a slow soulful song and started slowly dancing and gyrating in front of me. She swayed in time to music and pressed her ass onto my lap. The friction of her movements on me made me start to get hard. After half a minute of that she stood up and faced me. She undid her green bra and cupped her breasts without letting me see them at first. She made the bra fall to the floor, but still cupped her nipples. She straddled me and let her palms fall away from her nipples. Her tits looked even better up close. They sagged some, but I expected that. Boobs that big can’t defy gravity. Her areola were pebbled and roughly as big around as silver dollar coin. Her nipples were hard and about the size of a thimble. Their pink color was a nice contrast with the pale flesh surrounding them.
I longed to put one in my mouth, but I wasn’t about to touch her and have the show cut short. Stephanie draped her huge boobs in front of my face, giving me a fantastic view. All the while, she was dry humping my crotch. The song ended and she sat back down next to me.
I said “your boobs are magnificent.”
She laughed and said “magnificent! Haven’t heard that one before, thank you. They were even better 10 years ago.”
I said “I don’t see how, they’re perfect to me. And I just examined them very closely.”
I was surprised to see she blushed a little and said “well thank you. Ready for the next song?”
I nodded and she started a classic rock song next. Stephanie danced faster to this song, which caused her large tits to bounce and sway even more. She turned around and bent over so I could get a nice view of her round ass that was barely covered by green panties. As she danced, I could also see the outline of her pussy lips. God it was hot. She stood back up and looked at me over her shoulder. I smiled at her and she tucked her thumbs in the waistline of her panties. She then bent over, taking them off and fully revealing her big, pale ass cheeks, and her outer pussy lips. My cock was hard as a brick inside my pants. After I got a long eyeful of her ass, she turned around and I finally got to see her fully naked from the front.
She had a trimmed black triangle of hair above her pussy that looked amazing. I love hairy bushes. She then straddled me again and rubbed her naked cunt on my cock through my pants. Her arms were wrapped around my neck and her tits were right in front of my face. Stephanie really seemed to be getting into the dance when the song ended. My breathing was faster and I had sweat on my forehead.
I said “your body drives me wild. I really prefer hairy bush over shaved too. That was a nice surprise.”
She replied “good, a lot of guys aren’t into it. Especially younger guys. Time for your last song.”
She started a new classic rock song and dance walked toward me. I ached to touch her, but I kept my hands on the couch instead. She stepped onto the couch, putting one foot on either side of me. Her pussy was directly in front of my face as she stood in front of me and slowly gyrated her hips. I groaned as her cunt was only a few inches away from my mouth. I wanted to jam my tongue in so badly. I was breathing even harder at that point, and I could smell how aroused she was getting. She really was getting turned on, I thought. I was painfully hard as her pussy nearly brushed against my lips. She used one hand to spread her lips wide so that I could see her inner lips and clit. She was wet and I could see her juices glistening on her pink lips. I could hear the song about to end and I knew that beautiful snatch would be taken away.
As the song ended, she sat back down and said “three dances is usually the end of private dances.”
I sighed wistfully and said “okay, thank you, that was incredible.”
She asked me “what’s next for you? Back to the show?”
I replied “no, I think I need to go home and jerk off, you made achingly hard. Then I’ll probably go get some late night breakfast. I’m starving now.”
She said “those both sound good.”
Was that an interest in coming with me? I looked at my watch, it was 12:16. The club was open til 2am. I said “it’s probably a big nono at the club, but would you care to join me?”
She said “that is a big nono, but I think I would. I’m turned on, and I think you deserve more than just those three songs for helping me out with my rent. 8kll leave early tonight. Give me 10 minutes to change clothes, and I’ll meet you out front.”
Hell yes, this was turning out to be a good night after all. I went to my car, ran my fingers through my hair and put a couple of mints in my mouth. After about 15 minutes, she walked out and looked around. I flashed my lights and she headed toward my car and she got in the passenger side. Stephanie had changed into a pair of jeans that hugged her big ass and a tight t-shirt. I was pretty sure she wasn’t wearing a bra. She pulled the visor down and looked at her reflection.
She said “thanks again for buying that dance. I was $300 short and had barely made $50 all evening. And thanks even more for not being a creep in the Champaign Room. I thought for sure you were going to expect me to blow you or something in exchange for the money. But when you were ready to leave afterward, I knew you were probably a decent guy.”
I said “I think I’m pretty decent. Honestly, I’m new in town and really wanted someone to talk to. Don’t get me wrong, the dance was great and I wanted nothing more than to grab your boobs, but I would’ve been perfectly happy just talking to you. It’s been pretty lonely since I moved here. So thank you for coming with me.”
She said “I knew you were different when you asked my real name. In all the years I’ve been ‘Midnight’, you’re the only guy to ever ask me that. Before we go eat though, I want to thank you properly.”
Before I could say anything, she reached over and rubbed my cock through my pants. I was still semi-hard, and quickly became fully hard again. I let out a soft groan as her hand moved.
She said “there’s a parking lot around the corner that’ll be empty, go over and park.”
I did and she unbuttoned my pants and pulled my cock out. She stroked me a few times, smiled, and said “I don’t ever do this. Lots of guys always try of course, but I always turn them down. I like you though, and it’s not every day that an actual gentleman walks into a gentleman’s club.”
I wasn’t about to stop her but I wanted to make my intentions clear and said “okay, but only as long as you want to and not because you feel obligated.”
She leaned over and kissed me on the cheek before she lowered her head down to my lap. While still stroking my dick, she started to lick the head. My hips bucked once in response. Then she sucked me into her mouth. I felt her tongue swirl around the top half of my shaft as she sucked and her I saw her cheeks cave in. I moved my hand over to her ass to rub it through her jeans since she was on her knees in the passenger seat.
I asked “is this okay?”
With my cock still in her mouth she let out a muffled “mmhmm” so I continued to rub and squeeze her big ass as she blew me. Stephanie had started to bob her head up and down with her lips suctioned firmly to my shaft, which made loud sucking and slurping sounds. This was easily the best blowjob I’d ever received; Stephanie really knew how to suck dick. She’d only been sucking me for about five minutes and I was already close to busting. Mostly because I had been so turned on from her dances and cunt right in my face earlier. I wanted to hold out longer, but right then, she took my whole cock into her mouth in a deepthroat.
I’m a little above average size-wise in my pants. Not porn-big, but I have to buy Magnum condoms, so I’d only ever been with one girl in the past who could deepthroat my whole dick. I moaned out loud as I felt her lips on the base of my shaft.
I warned her saying “fuck I’m going to cum!”
She raised her head up until just the head of my cock was in her mouth and used her hand to stroke me hard and fast, using her other hand to tickle my balls. I squeezed her ass harder and let out a low groan as I started cumming into her talented mouth. She let out a surprised “mmm!” sound as my first burst of spunk shot into her mouth. She kept stroking me, working out five or six more shots into her mouth.
Finally, my orgasm subsided and she lifted her head up and let go of my prick. When she looked at me, she had her lips pursed and I knew my cum was still in her mouth. Stephanie opened her mouth a little to show me my white cum pooled in the bottom of her mouth before she swallowed it all.
She coughed on it and gagged a little saying “damn! That was so thick!”
I apologized saying “sorry, it’s been over a week since I’d gotten off and I was really turned on by your dances earlier. I hope it wasn’t too bad.”
She said “oh no, not bad at all. It was just more than I was expecting. If you want, you can take me back to the club now.”
Crestfallen I said “I thought you wanted to go get breakfast?”
Surprised she said “oh I do, but I thought after that you might be done with me.”
I said “no way, not unless you want the night to be over. Let’s go eat and then if you’d allow it, I’d very much like to return the favor.”
She grinned and said “okay, let’s go.”
I put my cock back in my pants, started my car, and drove to an all-night diner she knew. We chatted while I drove. She was divorced, had one adult-aged son, and had a small apartment where she lived alone. I told her that I had no kids, and had never been married. I told her about my new job as an office manager at a real estate firm. Stephanie was funny and easy to talk to and we made one another laugh. I pulled into the parking lot of “Anne’s Diner.”
I said “I wonder if Anne is working at 1 in the morning.”
She chuckled and said “I’m pretty sure that’s just a name. But this place is great. A lot of the dancers come here after shift.”
We went inside and sat at a booth. A server came by and we placed our orders. OJ, sausage, toast, and pancakes for me, coffee, bacon, hash browns and eggs for her.
She said “the waiter probably thinks I’m your mom.”
I said “oh come on, you’re probably not that much older than me. What? 45? 47?”
She laughed and said “you’re sweet. But I’m a few months shy 59.”
I was a little surprised because she really didn’t look that old. I shrugged and said “so what? I don’t care if you’re older than my mom.”
Stephanie grinned and said “if you don’t think it’s weird, Will, neither do I.”
Just then the food came out and our conversation died a little as we ate. The breakfast was excellent. You can’t beat a good diner breakfast. Once we finished eating, we sat and talked for a while longer.
I asked “would you like to come back to my place?”
She nodded and I left cash on the table before we left together. I held my elbow out and she hooked her arm in mine. I drove us to my apartment that was only a few miles away. I unlocked my door and she looked around. There were still moving boxes and nothing on the walls yet. She sat on my couch and I asked if she wanted anything to drink, but she declined. I sat down next to her and she scooted next to me and started kissing me.
As she stuck her tongue in my mouth, I slid my hands up her shirt. She wasn’t wearing a bra and I finally got to squeeze her big tits. I massaged them and gently pinched her nipples. She moaned into my mouth and then broke the kiss. I lifted her shirt up and she raised her arms up so I could lift it over her head. Her big boobs had a little sag to them, but I loved them. I went back to squeezing and kneading them. Her eyes were closed as she enjoyed the massage.
After a couple of minutes, she opened her eyes and said “what do you want do next?”
I said “I want to do down on you. I was dying to in the club.”
She grinned, stood up and took her jeans off. She wasn’t wearing any panties either and said “don’t have to twist my arm!”
Stephanie sat back down on the couch and spread her legs wide. I put a couch pillow on the ground in front of her. Her pussy was nearly dripping as I knelt in front of her. I lowered my mouth down and licked her from the bottom of her lips all the way to the top. She shivered once and let out a sigh. I pressed my mouth to her pussy and pushed my tongue into her. My nose was pressed into her bush as I licked her. I moved my tongue upward and found her clit and she let out a loud “oh!” as I flicked my tongue on it. Her pussy lifted off the couch cushion and forced my mouth onto it harder. She was nearly panting at that point.
I kept up my stimulation as I inserted two fingers into her wet pussy. She grabbed my hair and made a groaning sound. I plunged my fingers in and out faster as she held her breath. She pulled my face harder onto her pussy and I felt her cunt contract on my fingers harder. I tasted her get even wetter. A tangy, salty taste. I didn’t really enjoy the taste, but it wasn’t totally unpleasant. I kept up my licking and fingering as she came. She let out a deep, long moan and her breathing gasped out. She clamped her thighs almost painfully around my head as she rode out her orgasm. I stopped licking her but kept slowly fingering her.
She flopped back against the couch and said “you can stop. Fuck that was so good. It’s been months since someone else has gotten me off. It’s usually just me masturbating in bed, or in my bathtub.”
I grinned and replied “glad I could make you cum so hard.”
I stood up and my cock was tenting the front of my pants. She saw it and leered at me. She sat up and unzipped me. I let my pants fall and stepped out of my shoes, pants and underwear. My prick stood straight out and she took me into her mouth for the second time that night. It felt great but after just a few seconds, I stepped back out of her mouth’s reach. I wanted to get into her pussy. She leaned back and I spread her legs, allowing me room to kneel between her legs. I guided the head of my dick into her pussy entrance. I slid it up and down a few times to lube the head with her juices. I gently pushed in until my entire length was inside her.
We locked eyes as I entered her and she sighed when my balls brushed against her ass. I didn’t move at first. I just enjoyed the feeling of heat and pressure of her cunt engulfing me. Stephanie was tight, soaked, and warm. I hadn’t had sex in nearly five months and was glad that she had blown me earlier. If she hadn’t I probably would have cum too early.
I reached up and started squeezing her boobs again as I started sliding my cock in and out of her in long strokes. I pinched her nipples and she smiled up at me. I looked down and watched my dick hump into her wet cunt. It was making a squishing sound as I nearly pulled out completely before thrusting back in. It was such a sexy sight and sound.
She said “mmm, your prick is perfect. Fuck me harder.”
I picked up my pace and started humping into her harder. The faster thrusting made her tits bounce up toward her neck and then back down toward her belly button. My hips were making a slapping sound as I slammed into her over and over. I could feel my orgasm starting to build. I kept my pace up though.
I used my right thumb to find Stephanie’s clit and started rubbing it. She let out a moan and said “god, that’s good, keep going. Make me cum on your cock. Fuck.”
I thumbed her clit faster as I slammed in and out of her cunt. Her hair was sticking to her forehead because she was sweating. Abruptly, she pushed my hand away from her clit and her second orgasm started. She arched her back up from the couch and her pussy contracted around my plunging cock. Stephanie let out a string of groaning curses as she came hard from my fucking.
I managed to hold off and continue to stroke in and out of her more slowly until she had stopped cumming. When she was finished, I pulled out and jerked off a few times. My dick was sticky with her cum as I stroked. After a second, I grunted and came on her stomach. My first shot hit near her belly button. My second landed in her cleavage. I stroked out three more shots onto her black triangular bush. I was huffing and puffing and I felt sweat drip down my back. Stephanie was splattered with my spunk from pussy to chest.
I said “that’s the sexiest thing I’ve ever seen.”
She giggled and said “you came like a champ! Can I get cleaned up in your bathroom?”
I nodded and showed her where it was. I pulled two wash rags off the rack and wet them with warm water. I handed one to her and left her in the bathroom. I cleaned my cock off and went and laid on my bed. A minute later, I heard the toilet flush and she walked into my bedroom. She laid next to me and rested her head on my chest.
I asked “want to sleep here, or do you need me to take you back to the club?”
She asked “can you take me in the morning?”
I said “sure. If you’re game, I’d like to take you out. If you’re not interested, I understand though.”
She looked up at me and asked “you want to date a stripper that’s old enough to be your mother?”
I said “no, I want to date a beautiful and interesting woman. Your age and what you do for a living don’t matter.”
She smiled and said “oh, well, okay then.”
She fell asleep in my arms and I nodded off shortly after.
***
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