The week of Thanksgiving is busy for all of us here in the USA.  I, M55, spent the early part of the week planning for the arrival of my kids who were coming home from college and graduate school on Wednesday.  I have been divorced more than two years, but my kids always come to my place for Thanksgiving as I serve Prime Rib (rather than turkey) and generally avoiding the stress and hassle of the myriad side dishes which make the holiday so much work to both cook and clean up.  My kids prefer the relaxed atmosphere of how I celebrate my holidays and it’s a fun day for us to mix some cocktails, eat good food and watch football while we catch up about their progress at college.

Since I’m back in the single dating population, I have spent a decent amount of time trying on-line dating. I’ve learned the hard way to spot red flags and scammers, so by the time I’m done sifting through that means, if I get a like or a match, I’m realistic enough to expect it to result in a real date only 10% of the time.  On the Monday before Thanksgiving, I was on Facebook reading posts about my relatives plans to celebrate the holiday. I looked down and noticed a rare like button in my dating inbox, so I opened the link and found myself looking at the profile of (call her Ana), an attractive Indian (south Asian) woman in her mid 40’s.  Ana’s location stated she lived in an area which could either be a neighborhood 10 miles from me or a city 100 miles away as both share the name here in SoCal. 

I typed a message to Ana saying that I thought her pictures were really cute and hoped she lived in the neighborhood close to me as I don’t like to date further than 30 miles away.  Ana immediately replied that unfortunately she lived in the city 100 miles away.  I wished her the best of luck in her search as I informed her that I had no interest in driving back and forth 100 miles, which in Southern California, can sometimes mean four hours each way in traffic.  Ana immediately replied that she was going to be in my city for the Thanksgiving holiday visiting friends and was available to go out for a date on Friday or Saturday if I was interested in meeting her.

At this point I was faced with a conundrum. I thought she was cute and from a personal standpoint, I’d never dated an Indian woman (though I did date a Native American for a few weeks two years ago).  Dating (and banging) an Indian woman was still on my bucket list, but I didn’t want to waste my time in going out for a date when there wasn’t going to be any hope for sex. 

I decided to cut to the chase and I asked Ana if she was looking for a friend or a hook up, noting my stance on not dating long distance.  Ana replied that she wasn’t down to “just have sex” but she appreciated that I wasn’t looking to waste my time or hers and “thought we could have some fun”.  I was honest with her and told her that on Friday night I was already scheduled to have my second date with a woman that I’d just met last weekend and that I was supposed to go tour an old hotel here in town known for its holiday lights, so I told Ana that I doubted I would be available. 

Ana replied that she thought my date sounded really boring with a wink emoji. She surprised me by sending me her phone number, then she told me to text her when I finished up my date. I replied no promises however I did say hi via text since I had her number.  After my kids departed on Friday, I picked up my date (call her Kate) at 6 p.m.  Kate is an attractive white woman two years older than me.  We had spent the previous Saturday night getting to know each other at an Italian restaurant and I had enjoyed her company, though she spoke about her grandkids more than I desired. Even though she is attractive and presentable, as we toured the hotel’s holiday lights, I soon realized that there wasn’t any spark between us.  By 9 p.m. Kate was yawning and I asked if she was ready to head home.  Kate nodded and I drove her home.  Kate politely pecked me on the cheek and closed the door behind her as I bid her good night, reminding myself to do the right thing the next day and drop her in a kind way, citing incompatibilities. 

I sat down in the drivers’ seat and still energized, looked up Ana’s number.  I texted her a quick “wyd” (what are you doing), but doubted I would get a response.  By the time my tires were fully out of Kate’s driveway, Ana surprised me by sending me an address to a billiards/pool bar 15 minutes away.  I thought “why not?” and drove over to the address on my phone. 

I pulled into the parking lot a few minutes later and walked into the bar. There were 12 or so billiard tables in the place, all occupied by groups of 4 or so shooting pool.  I found Ana seated at a high-top table next to a pool table where her two girlfriends were entertaining themselves by taking random shots with apparently no clue of what they were doing. Ana recognized me first.  She called out my name and waved me over to their table. I gave her a quick hug, ordered a beer from the waitress as she passed by then I sat down next to Ana. She was more curvaceous than her pictures had shown and even more brown and exotic looking than I expected, almost like a Mia Khalifa type of body but her skin was even darker. Her hair was shoulder length and was a pretty, almost bronze color. Her sweater revealed a big set of boobs which seemed to be straining at the fabric while her booty was nicely apple shaped against the tight skirt.  I spent a few minutes chatting and flirting with her before getting up to take my turn on the billiard table as her friends had decided they were going to team up to play against me. I put the billiard balls into the triangle and I broke it hard so that the balls would spread around the felt to make shooting easier for everyone.

I realized that Ana was pretty tipsy as she repeatedly grazed her hand over my ass every time I sat down from taking my turn on the pool table. A few minutes later I finished the game (8 ball side pocket) her two girlfriends announced that they were taking a break to go smoke a cigarette outside.  Once they were gone, Ana turned to face me.

“Do you think I’m cute?” Ana asked shyly.

I reached over and cupped her face with my right hand then decided to roll the dice and pulled her into a quick kiss. “I think you’re sexy as hell!” I replied. She smiled then pulled me in tighter and started kissing me with an urgency that I didn’t see coming, shoving her tongue down my throat with no regard for the people playing pool around us.  We finally broke for air a minute later.

“Do you want to fuck me?” She purred in a soft whisper into my ear.

I was shocked by her direct approach and nodded my head.  I paid the bar tab with cash to save time, grabbed her hand and walked outside where we found her girlfriends smoking their cigarettes.  Ana walked up to them and spoke to them in their native dialect (turned out to be Bengali) for a minute, then she turned and asked where I’d parked my car. 

I guided her to my car and opened her door.  As soon as I sat down in the driver’s seat she leaned over to kiss me again, aggressively forcing her tongue down my throat while her hand started pawing at my cock. 

“Let’s hold that thought for ten minutes until we get to my place,” I suggested, pulling away to start the car.  We made small talk during the drive about how we had spent Thanksgiving, but the sexual tension in the air was palpable.  I parked my car in the driveway of my house a few minutes later, then gave her a quick tour of my condo and of the view. She couldn’t have cared less.

“Where’s the bedroom?” Ana asked with a slight pout. “Aren’t you going to fuck me like you promised?”

I kissed her then pushed her backwards down the hall to my bedroom, which thankfully I had straightened up that morning. Once in my bedroom, she promptly kicked off her shoes and threw her jacket and purse over a chair in the corner. She sidled up to me and we started kissing, tongues dancing as her hot (and Scotch tasting) breath mingled with mine. I reached around her waist to undue the clasp on her skirt and once that was undone, managed to pull the zipper down as well.  Ana stepped out of the skirt then wordlessly pulled her sweater over her head, leaving her with only her matching jet black bra and panties.

My initial thoughts about the size of her tits proved to be true as her bra straps cross behind her neck in order to support the DD cup size. I reached around and undid the three clasps (years of practice have helped in that effort) in the back from bottom to top then she wriggled free from her bra and panties.  Her huge tits practically rebounded from the explosion out of her bra as her girls were yearning to be free. Her aureloas were average size however her nipples stood out like blackened bing cherries, ripe for sucking. I pushed her back onto my bed then I grabbed each tit with an opposite hand and leaned down to suckle one nipple then the other while my opposing hand played with the other tit.

“Bite them!” Ana commanded.  I nodded at her command with a mouthful of left tit and slowly played with her nipple between my teeth, gently increasing the pressure to see where she would tap out.  It turned out that she was somewhat of a pain queen and she finally drew a hiss of air in when I finally clamped down a little harder.

“Omigod I fucking love having my nipples bitten!” Ana yelped as I replaced her right tit into my mouth, clamping down slowly until I reached her limit.  I kneeled between her legs, still clothed, alternating biting her nipples as instructed until I felt her hands on my shirt, awkwardly tugging at it.

I stepped up and quickly took off my shirt, pants, socks and underwear in a blur of motion, revealing my now hard 6” cock. (Reader’s note, I could lie and say that I’m huge, as its certainly not a porn star cock, but I’ve always been happy that it gets the job done on more than one occasion, so why lie?).   She knelt between my legs and started giving me a blow job.  Her desire was off the charts however her technique was found wanting as she wasn’t great at maintaining any kind of rhythm.  Still, it was fun watching my pink cock slide in and out of her brown mouth so I leaned my head back and relaxed, savoring the sensation.

After a few minutes, I decided to return the favor. I leaned over and lifted her off of her knees and gently placed her back onto the bed, then nudged her panties over each hip until I could pull them off easily. Her legs were hanging off the edge of the bed so I wrapped her knees around my head while I dove into her pussy. Her pussy lips were small and more innie than outie. She tasted very sweet and was freshly shaved.

“Did you shave your pussy for me?” I asked between long licks up and down the slit of her pussy.

“Yes!  Can you tell?”  She whimpered. “I shaved it this morning in case you called me back.”

“Good girl,” I murmured, then I started focusing on her clit. Her hips instantly bucked as soon as I had pursed my lips around the little nub, alternating between sucking and licking it in a steady rhythm for a few minutes.  I felt her getting closer and watched her hands make fists on the top of my bedspread, so I knew she was close.  I decided to edge her for the time being, so I backed off licking her clit and instead put two fingers inside of her, searching for the sensitive little walnut on the roof of her pussy.  As soon as I found it she arched her back again and started scratching her long nails on either of my shoulders, sometimes digging in with her nails when I found a special spot, urging me on by raking her nails across my deltoids.

Ana seemed to be building up to an orgasm so I decided to finish her off by adding my tongue back to her clit, simultaneously playing with her g-spot and her clit at the same time.  Ana was writhing and bucking her hips into my face and I saw her face tense up and release as she whimpered that she was coming. I maintained the pace and pressure of my tongue and fingers for another minute to see if I could bring her to come again but she pushed me away, saying she was too sensitive.

I gave her a bottle of water to take a break and she gratefully took a swig, however she noticed that I was still hard so she gave my hard cock a gentle tug.

“Can you put a condom on him and fuck me with it?” She asked with a coy smile.

“I had a vasectomy a few years ago,” I responded. “Are you worried about pregnancy or STD’s?”

“Pregnancy,” she responded. “I’m literally ovulating today and I’m horny as fuck, if you couldn’t tell.”

“I may have noticed,” I replied with a grin. “But I’m shooting blanks and had a STD clear panel a few weeks ago so I’m clean. What about you?”

“Me? I don’t meet men very easily,” She replied. “I haven’t been fucked properly in a long time so I’m clean as well.”

“In that case, I’ll just fuck you bareback,” I stated, then took the bottle of water away and set it on the side table. “Where do you want me to come?”

“I love watching it spit on my tits,” Ana stated with a devious wink.

I nodded in assent, then pushed her back onto the bed again so that her ass was just hanging off the bed. I pushed her legs apart and she quickly wrapped them around my back, pulling me into her as she guided my cock into her warm, velvet pussy with her left hand.

I was surprised at how tight her pussy was given that she’d had a few kids back in her twenties. It took me a few strokes in and out, meeting resistance before I was finally able to bottom out. Ana did her best impression of a cowgirl at this point as she bucked under me while digging her heels into my ass with surprising strength. I started slow, kissing her mouth and dipping low enough between kisses to nibble on her nipples, however Ana was ready to get fucked. She alternated between moans and shrieks of delight on every thrust, which I realized was really turning me on as the last few women I’d been with were surprisingly quiet in bed. Ana had a primal desire to be fucked hard, and she had no qualms about urging me to fuck her harder with every stroke.

Normally I like to take my time and alternate between slow, sensual and jackhammer thrusts however something about Ana just told me to fuck the living shit out of this woman as hard and fast as I could.  I was glad that I’ve worked myself into better shape over the last few years (thanks fasting and HIIT training lol) so I was able to maintain the pace for a solid five minutes before I felt the pressure build in my balls. I pumped my hips a few more times then pulled out of her dripping cunt.  My cock was coated with her juices so it was easy to finish myself off with a few pumps of my hand. 

The first spurt was a doozy and hit her throat and chin, which gave me immense pride as my cock was perched right above her pussy.  The next few pumps weren’t quite as far as I managed to paint each one of her big tits with a nice glob of cum (inspired by Jackson Pollock lol) before I shot my final spurt of warm cum onto her belly.  Ana immediately started scooping up the largest globs of cum and greedily sucked her fingers. I decided to help and spoon fed her the last drops of cum that I could find on her tits before she gratefully wrapped her arms around my shoulders, pulling me into her for a long kiss.  I could faintly taste the salty aftermath of my cum on her lips, and laughed as I felt my chest hair get wet with the remnants of my hot load on her tits as we rubbed against each other.

“How long does it take you for Round 2?” Ana asked after I collapsed onto my back next to her. I pulled out a packet of wet wipes from my bedside table to clean off her chest but she pushed them away. “Don’t clean me just yet. I like feeling all gooey.”

“It will take a few minutes to go again,” I replied with a chuckle. “I’m 55, not 22.”

“Do you need to take another Viagra?” Ana asked.

“I didn’t need to take one for the first time so I don’t think I need to take one for the second time,” I replied.

Ana was impressed. “My ex needed to take them by the time he was 40 just to get hard once,” she noted.

“We’re all built differently,” I replied with a shrug. “My cock isn’t huge but it always works on command so I have to be happy with that.”

“How can I help you get hard faster?” Ana asked earnestly but with a sense of underlying urgency. “I really want to fuck again like right now.”

“Have you ever rimmed a guy?” I asked with a doubting grin. “It’s always turned me on but not all women are into tonguing a guy’s ass.”

Ana seemed to contemplate the request for a moment, then shrugged her shoulders.  “I’ve never done it but I’ll give it a try. Give me a wet wipe so I can clean your ass, then I’ll try it.”

I did as instructed then turned over and arched my back, putting my face onto the bed doggy style. Ana spread my ass with one hand while she wiped my butt clean with the other. She noted that my ass was bereft of hair like my balls and taint, which I started manscaping a few years before and regularly maintain for cleanliness now. Once Ana was satisfied that I was clean, she gingerly knelt between my legs, then spread my ass cheeks with either hand until my puckered starfish was fully exposed.  She kissed at it a few times then started exploring my ass with her tongue. 

The sensation of her tongue in my ass was exquisite. It started as a tickle but kept growing in pressure and sensation. I groaned with pleasure, then reached down between my legs to start jerking myself off. Ana got the hint, so she reached around my leg and replaced my hand with her own. Soon she was tongue fucking my asshole while jerking me off, and I felt my cock hardening towards a full erection.

“I’m hard,” I panted, squirming between her tongue thrusts into my asshole. “Do you want me to fuck you now?”

“I’m not done here yet,” Ana giggled, but her voice was muffled as she talked to my ass between tongue fucks. “Just enjoy it.”

I managed a strangled moan in reply as she thrusted her tongue even deeper into my asshole while increasing the pace of her handjob.  Unfortunately, my cock was now dry and her hand pumping my cock was starting to feel like sandpaper against the sensitive skin. I reached over and opened my side table for some lube and handed the bottle to her, but she misinterpreted the message.

“What’s this? Lube? Do you want to fuck my ass with this?” she asked in astonishment.

I hesitated, then turned over onto my back, trying to contemplate the right answer. I decided to lob the question back to her.  “Yeah. That would be fun.  Do you want me to fuck your ass with this?”

She furrowed her brow in deep thought for a minute, then handed me the lube and dove face first into the pillow next to me. “Okay, but you have to lick my ass first. It’s only fair.”

We exchanged positions so her head was face down and her ass was up.  Since I had the wet wipes on the table next to me, I decided to return the favor and clean her asshole with the same technique she’d used a few minutes before. I put my hand on her left ass cheek and pushed it wide to the left while I covered my right thumb with the wet wipe and gently inserted it into her puckered ring. She inhaled sharply, air whistling between her teeth as she adjusted to the pressure. I cleaned her for a few seconds, then tossed the wet wipe on the floor and replaced my thumb with my tongue. Ana’s body convulsed with pleasure as she felt my tongue snake itself into her asshole, then she collapsed off her elbows until she was face down on the pillow, whimpering each time I completed a round robin swoop of my tongue in her ass.

I maintained an even rhythm for a few minutes, tonguing her ass ten ways from Sunday while giving my semi hard cock a jerk every few seconds to maintain the tumescence. Finally satisfied that I’d repaid the favor and then some, I grabbed the bottle of lube off the bed next to her foot and liberally applied a coating of lube all over my cock. I applied a similar glob onto her asshole and then trailed some more lube up her asscrack so that the excess would slowly drain down to her asshole while I was fucking it.

“Are you ready?” I grunted into the back of her head.  She nodded, then reached behind to pull her cheeks apart. I gave my cock a few hard pumps to harden it as much as possible while also applying the lube onto the tip, then guided the head towards her little starfish. It took a few attempts to get past that ringed gate, but once the head of my cock penetrated into her, her body shuddered and spasmed while she cried out in both pleasure and pain.

“Ohmyfuckinggod!” Ana murmured into the pillow while her hands were making fists on my bed sheets, slowly pulling the sheet off the bed as she did. “Go slow!”  I did as commanded for a moment, slowly easing my cock into her tight little asshole inch by inch until I was at full hilt. Satisfied that she could take me, I started increasing the pace of my strokes, reveling in the sounds of her grunts and cries each time I bottomed out. My pace increased and I could feel my balls slap against her clit however Ana decided to aid her own pleasure at this point, fingering her clit with a furious energy.

“Are you going to come in my tight little asshole you fucker?” Ana shrieked as she started building herself up to another orgasm. Her legs started to spasm and I felt her feet cross behind my ass, pulling me farther in as I increased my pace until I was jackhammering her asshole. I soon felt my balls tighten and soon started shooting my hot load deep into her ass. Her asshole milked the remaining cum from my cock as we both stopped cumming, then I collapsed me weight onto her back, breathing heavily into the back of her now sweaty hair until she turned her head enough to face me.

We both laughed, then exchanged a kiss. I felt my cock shrinking by the second inside of her ass, then gently pulled myself out of her, rolling over onto my back in the same motion. I inspected my cock, which was relatively clean, then wiped myself off with another wet wipe. Ana groaned into the pillow, then rolled over onto her back and then excused herself into my bathroom. She emerged a few minutes later, then walked over to check her phone.  “Oh shit, I’ve been here longer than I thought!” she muttered.  Ana’s hands flew over her phone, exchanging texts with her friends.

“Any chance you can drive me back over to where we first met tonight?” she asked, pulling on her panties and bra.

“I don’t have any place to be in the morning,” I replied. “Are you sure you have to go?”

“We’re supposed to go shopping with her kids early tomorrow morning,” Ana stated, pulling on her shirt and pants. “Get dressed.”

I jumped into the bathroom to brush my teeth, then pulled on a pair of sweats that I lazed around the house with. I grabbed my keys, wallet and phone from my pants on the floor then grabbed two bottles of water out of my fridge as she hustled me out the door.

We drove silently back to the neighborhood where we’d met two hours before. Halfway there, Ana squirmed in her seat.  “I can feel your cum leaking out of my ass,” she observed wryly.  “I hope my friends don’t notice a big cum stain on my skirt.”

“I’m pretty sure they have figured out that we’ve been fucking,” I replied with a smile.

Ana laughed at the thought, then grabbed a few breath mints from the console of my car as we pulled up to the bar’s parking lot. Most of the spaces were empty, however her two friends were waiting for Ana in the front seat of an SUV, quietly munching on some bags of fast food I couldn’t identify.

“Call me next time you’re in my town,” Ana stated with a grin, then gave me a quick kiss on the cheek before she skipped into the backseat of her friends SUV.

I drove home, wondering what the night after Christmas has in store for me.

Happy holidays!