I boarded the train in Bridgeport, Connecticut, sat down in my seat and sent a text to Naomi to let her know I was en route to Manhattan. 

As I settled into my seat a feeling of bliss washed over me. Excited to be heading back to the city. Excited to do some solitary reading on the train ride. Excited for the rendezvous with Naomi.

My wife Jane and I moved from the city up to Bridgeport a couple of years ago. For the typical reasons that a couple approaching their fifties in Manhattan do. Namely, our son had left for college and we’d be closer to him in Bridgeport. And secondly, we were just at the point in our lives where the tranquility of suburban life was appealing.

And we were both quite happy about the decision. It was made easier by the fact that we owned a pied-à-terre in the east village. It was the first place I bought when my cofounder and I sold our publishing startup in the late 2000s. We outgrew it years ago but kept it and rented it out until our tenants moved out shortly after we moved to the suburbs. We didn’t need the extra money and wanted a place to crash when we came into the city. And so when I had to go to the city for work or got the urge to go see some live music or some art, we were a quick train ride away. Jane and I would sometimes go together, but more often than not, I’d go solo.

For the last several years, I’d been working for one of the smaller publishing houses, helping them with their web products. I was passionate about literature but my skills were in building web products, so it was a perfect gig for me in my semi-retirement. Plus, their main office was in midtown and so it gave me one more excuse to make periodic train trips down.

—

I met Naomi through my former cofounder, Bill. She was an admin at the tech company Bill started after we sold the startup he and I worked on together for years. Bill’s company was having an event one evening when I happened to be visiting and we hit it off. She was an aspiring writer and a big reader and there was a lot of overlap in what we had been reading lately and so there was a lot to talk about.

Nothing happened, but when I told her where I worked and about some other connections in the publishing world, we exchanged email addresses and I promised to make some connections for her.

We ended up exchanging a bunch of emails over the ensuing weeks and as luck would have it, one of my connections resulted in a one of her short stories getting picked by one of the big literary journals. 

She was ecstatic. And told me next time I was in town, she would buy me dinner. I told her she didn’t have to do that but I did write her next time I was coming in to the city and told her she could buy me a drink instead.

And so that’s how I ended up meeting her at the bar around the corner from the studio in the east village one Thursday night.

I was sitting down at a table nursing a beer when she spotted me and ran over. She hugged me tight and thanked me profusely for the help. She asked me for my drink order and came back to the table a few minutes later with a couple of martinis. I finished my beer while she took off her jacket and sat down. And then we clinked our martini glasses together.

She told me the sequence of events that led to her getting her story published and what she was working on next and before I knew it she was back at the bar ordering another round.

I knew Naomi was a beautiful girl when I met her the first time but she looked absolutely stunning tonight. She was tall, probably around 5’9” and quite thin, with long, willowy arms. She was half Asian and had short, dark hair, and really short bangs that are popular with all the hip girls these days. She had on a casual grey dress with thin straps.

Over the second drink, I learned a little bit more about her. She was in her mid-20s and had been in New York for a couple of years. She grew up in California, just outside of LA in a middle class family. Her mom was first generation Chinese and her dad was a third generation Californian and worked in the film industry. 

It seemed like our hangout was winding down after the second martini, but just as we finished, we realized we had both just finished the same book. And so we decided to continue the conversation with dinner at a ramen place next door.

Two martinis and a beer are enough to get me pretty drunk and the meal was a bit of a blur, but we ended up talking about our studio apartment. I think I brought it up because I still have a pretty sizable book collection. Naomi couldn’t believe we had a studio in the neighborhood and demanded to see it and the book collection and so we stumbled over there after closing out at the restaurant. 

During the walk over there was palpable tension. We weren’t holding hands but I had my hand against the small of her back and she pulled me towards her in a sort of a side hug a couple times. 

We must have looked a little strange walking together like this. Over twenty years' difference in age, about five inches in eight and probably over 50 pounds of weight separating us. But there was definite chemistry. 

The studio was pretty tiny but nicely decorated and Naomi loved it. She picked through the book collection while I prepared a couple tumblers with small pours of Amaro.

I walked back to Naomi. She had her back to me and was leafing through a book. I handed a glass to her with one hand while I gently placed my hand on her back and looked over her shoulder at the book she had in her hand. She put the book back on the shelf and turned toward me, smiled a little mischievously and put her hand around my back and pulled me towards her.

I gently kissed the side of her neck, then her jawline, and then finally our lips met as we pulled tight to each other. She cooed a little as she noticed the firmness of my cock pressing against the side of her hip.

We made out as my hands explored her hips and her lower back, and eventually I guided her over to the bed. I sat down and had her stand up in front of me. She unbuttoned my shirt and I pulled her dress up and she took over and pulled it over her head and off. She was wearing a black lacy bra and matching panties. Her bra covered her small but perfect A-cup breasts. I guided my hands along her tiny waist and up to her bra strap and unclasped her bra while kissing her neck and chest.

I lay back on the bed to take in the sight in front of me. This beautiful lady with the most perfect shoulders and arms and perky small tits that seemed to defy gravity. She climbed onto the bed and straddled me and I put my hands around her midsection while we kissed. And then moved my hands to feel her breasts. I broke off our kiss to, one at a time, kiss each breast and play with the nipple with my tongue. While I did that, she reached down to my pants and rubbed my hard cock through my pants. I slipped off my shirt while she unzipped my pants.

I lay back on the bed and she pulled my pants down and my seven-inch cock sprang free. She knelt down on the floor and took me in her mouth. Her mouth was small, though, and she didn’t get very far down, but it still felt amazing. I took in this sight for a few seconds, but then I pulled her up on the bed and kissed her and whispered in her ear that I wanted to fuck her. She went over to find her purse, grabbed a condom out of it and tossed it to me as she pulled down her panties. As soon as I slipped it on my cock she climbed on top of me. She was tight but dripping wet and we went slow but my cock was soon all the way inside her.

Despite all the alcohol I was so turned on by this tiny beautiful woman riding me that I soon came so hard I thought I would black out. 

The next thing I knew it was morning and I woke to see her dressing and gathering her things. She smiled and kissed me a little timidly on the cheek and told me that she had to get going to work.

—

I didn’t see Naomi for a while after that but we texted quite often. We talked about the books we were reading. She was writing more and eventually she started sharing some early drafts of her stories with me. They were really good and I put her in touch with some of my contacts in the publishing world and she even had a couple of them published in some magazines.

When the first one got published, the next time I was in the city, we grabbed drinks to celebrate. It was a really fun night but considerably more tame than last time and we were mildly flirting but nothing happened. I got the impression she was a little embarrassed by our one-night stand. Mainly I think it had to do with the age difference and the fact that I was married. Also, she let slip that she was seeing someone and that they had moved in together.

—

We continued texting frequently. Her writing was doing really well but she still had her day job at Bill’s company and was finding it hard to find the time to write between the job and her boyfriend.

One day I got a frantic text from her saying that she had had a huge fight with her boyfriend and she needed somewhere to stay. And so of course I offered her the studio apartment.

By that point, my wife and I were barely ever making it into the city and so it worked out fine for Naomi to stay there for an extended time while she figured things out.

But then a few days later, Jane impulsively bought tickets to a play the next evening. And we would be staying in the studio for the night and taking the train home later the following day.

I texted Naomi and apologized and offered to book her a hotel and asked her to tidy the place and told her I would compensate her for the work. She was very cool about it and sure enough, we arrived to an immaculately clean apartment with no hot young ladies in sight.

My wife and I had a fun night and really great sex when we got back to the apartment. Being back there, though, made me think about my night with Naomi. I was craving being with her again and decided to try and make it happen.

—

A few weeks into her stay at our apartment Naomi texted me and apologized for staying so long and asked if she could stay through the following month. I told her it wasn’t a problem and she asked if there was anything she could do to thank me and I told her I needed to be there in a couple weeks and asked if it was okay if she had a roommate for a night. When she replied that she was happy to have me, my cock immediately got hard.

—

The purpose of the trip was work. Meetings uptown that spilled into a dinner with some colleagues. I finally escaped around 8 and texted Naomi that I was on my way. She texted back right away and said that she was just wrapping up drinks with a friend near the studio and asked if I wanted to meet her at the bar.

I strolled into the bar to find her sitting alone at the back of the bar. She looked incredible. A simple black tank top with no bra and baggy jeans. I love how sexy baggy jeans can be. They somehow still show off her tiny, perfect figure. We hugged, ordered drinks, and sat down. I was a little surprised – and maybe it was because she had had a few drinks with her friend – but she seemed really happy to see me and kept reaching across the table and putting her hand on my arm. And every time she did, we made eye contact and my cock stirred in my pants. We were both tired and agreed to head back to the studio after the first drink.

As soon as we were inside the door, she hugged me and thanked me profusely for letting her stay there. She gave me a mischievous look and told me she wanted to make it up to me. She slid her hand down to my pants and felt my rock-hard cock. She looked up at me and grinned and unzipped my pants. I helped her slip my pants and boxer briefs down and she started licking and sucking my cock. I guided her over the bed and sat down and pulled my pants off as well as my shirt and she got on her knees and continued sucking and jerking my cock. I guided her to stand up so that I could take her clothes off. I slid her tank top off and took each of those perfect A cup tits in my mouth one at a time. Then I slid her pants and panties off and I slid my finger over her pussy as I continued to kiss her tits and nibble on her nipples. I was thrilled to feel her pussy dripping. 

I couldn’t help myself and flipped her over on her back so she was lying on the bed. I told her I was going to fuck her and asked if that was okay. She smiled and nodded and rubbed her pussy and I slid my cock in. We both gasped in ecstasy as my cock easily slid all the way in. We kissed as my body lay on hers and I thrusted in and out of her.

With how amazing it felt to slide my cock in and out of her, it took all of my willpower not to cum immediately. I decided to slide her over to the edge of the bed so I could fuck her standing up. It let me admire her lithe body and watch her small tits jiggle as my cock slid in and out of her, while also buying me some time since this position didn’t usually push me over the edge.

I started pounding her harder and I could feel her pussy grip on to my cock ever so slightly harder. I started to let up a little bit, worried I was going to cum but, sensing this, she told me that she was close to cumming and to fuck her harder. She started to wriggle on the bed and I could tell she was cumming and that put me over the edge. I pulled my cock out and my cum exploded out. The first couple of lines of cum sprayed on and between her tits and then another spurt hit her cheek and then a final few more covered her stomach.

After taking a few seconds to gather myself, I apologized for getting cum on her face, saying that was the most I’ve cum in a long time. She laughed and wiped it off with her finger and then licked it off with her tongue and gave me a mischievous grin. I told her how fucking hot that was.

We cleaned up and got dressed for bed. Me in my boxer briefs and her in her panties and sheer white tank top. 

—

In the morning, I woke up early and hopped in the shower. By the time I went back to the bedroom, Naomi was awake and sitting up in bed and reading her phone. Seeing her in her tank top, nipples poking out, made my cock hard again. I tried to conceal it as I dressed, but Naomi noticed and put her phone down and crawled over to the bed and grabbed my cock with her hand. She started rubbing it and jerking it and commented about how hard I was. I told her how irresistible her body was and how horny she made me. She smiled and started sucking me. Her mouth was small but she was able to take me fairly deep. She also licked my shaft and balls, which drove me crazy. It wasn’t long before I could feel I was on the verge of cumming. I told Naomi and she just kept sucking. I exploded in her mouth and she kept sucking—the cum dripping out of her mouth and down her neck.

I told her I wanted to return the favor and pulled her panties off. I kissed her small thighs and worked my way to her pussy. I looked up at her and she smiled, the cum still visible on her chin and neck. She took off her tank top. I went to town on her pussy, circling her clit with my tongue. All the while fondling her tits with my hands and tweaking her nipples. It wasn’t belong before I could feel her pussy loosening and erupting in an orgasm. By then my cock was rock hard again and we proceeded to fuck again. We started in missionary and then she got on top and rode me until she came again. She told me she was too sore and tired to fuck any longer but told me to cum on her, so as soon as she slid off my cock and lay down, I straddled her and came all over her tits. She scooped some of my cum off her and licked her finger and smiled her mischievous smile.

—

After she showered, we hugged goodbye and went our separate ways. 

As soon as I found a seat on the train at Grand Central Station later that day I texted her thanking her for the fun night and morning and she wrote back saying that it was the least she could do for me for allowing her to stay at the studio. 

I had already sensed it, but it was the first explicit reference to the transactional nature of our current situation. And it got me thinking about where I could take this. 

I thought about it as the train worked its way underground up to Harlem and my cock stirred in my pants as I thought about our night together. As the train emerged from underground, I decided to be bold. I wrote her back and said that if she was going to continue to thank me like she did, she could stay there as long as she wanted.

A few minutes later she wrote back and said that as long as I let her stay there, I could come down once or twice a month and do whatever I wanted to her. 

—

I was reliving all this as my train passed through the same part of the Bronx going in the opposite direction. My phone buzzed with a reply from Naomi. She and the studio were all ready for my monthly visit.