[B/S] A Familiar Connection – MF, Slow Buildup – Part 1 of 4

(As always, please pardon the grammar errors. This chapter is pretty tame, but it’s setting the stage for our fun.)

I woke up and checked my phone, reviewing the new e-mails in my inbox. One e-mail was from the resort hotel that I was scheduled to visit in three weeks. I reluctantly opened it, already knowing what it would say: “we’re sorry, but with the current COVID outbreak, we’ve cancelled your stay.” Although this was expected, I was still disappointed. On the positive side, I now had a week of vacation scheduled which I needed to fill.

But before we delve deeper, I should provide some background. My name is Harry, I’m a mostly-heterosexual 34 y/o man living in San Francisco. I’ve lived in the Bay Area most of my life, but have never settled down or gotten married. I enjoy the city’s active social scene, and the adventurous playmates I’m able to spend time with. Since my girlfriend and I broke up last January, I’ve been in a bit of a sexual lull because the swinger clubs are closed (fuck COVID). I had hoped to meet some people at the resort, but that’s no longer an option.

With the quarantine, I’ve been feeling pretty isolated. I only have one sibling, an older sister, and we lost our parents in a car crash about ten years back. My sister Tanya is 36, and lives with her husband Brandon in a suburb south of the city. They don’t have any children and their house is pretty quiet, so I’ve been going over for dinner every two weeks. We have a pretty strong relationship, but the isolation of quarantine has hit Tanya pretty hard too. Every time I visit her home, she seems morose and doesn’t laugh as much as she once did.

Since the passing of our parents, Tanya and I had come to rely on one another for emotional support. We don’t have much local family, and I spend holidays with her and Brandon. As I laid in bed, I made a note to check on Tanya and see how she’s doing next time we have our family dinner.

As the thought left my mind, I checked my NSFW Reddit account and within a few moments, had a healthy erection. I hadn’t been intimate with a woman in over two months, and the drive to feel smooth skin under my fingers was becoming an obsession. My cock throbbed at the thought of hearing someone’s moans and heavy breathing beneath me. Before long, I checked one of my favorite subs, which was for Redditors looking for hookups in the Bay Area.

As I scrolled through the posts, one caught my attention:

“[F36] Looking for discrete playmate, hopefully big and virile.”

Intrigued, I clicked on the post and immediately laughed at the poster’s username: u/TightlipsSinkships. I checked their post history and noticed the account was three years old, but that they had no posts and very comments.

Her post said that she lived in the Bay Area and was suffering from cabin fever, and had been looking for an anonymous hookup. She mentioned that she had never done anything like this before and just wanted to go slow. Finally, she mentioned that she was married, but that she had her husband’s permission to explore something casual outside their marriage.

Reading her post, I was certainly intrigued and sent a chat message introducing myself. In that first message, I described how I was also feeling a bit cooped up, and that physical contact sounded especially good right now. I also mentioned that my job is somewhat sensitive, and that I’m only interested in discrete and anonymous activities. As I pushed send, I didn’t think I’d ever receive a response.

To burn off my horniness, I hopped on my stationary bike and road a few miles. As I rode, I couldn’t help but picture a beautiful woman spread before me, calling my name.

A few hours later, while working at the office, my phone suddenly dinged with the familiar sound of a chat notification. I opened my phone to see a response from Tightlips:

“Thanks for the message, sounds like we might be a good match! I know this might sound weird, but I’m not ready to meet in person quite yet. Can we just chat for a while and see if we click?”

I responded: “Of course, I’m happy to go at your own pace. I know you want to remain anonymous, so I won’t ask for personal information. Let’s just have fun and see if there’s a connection.” After I sent my response, I kept checking my phone to see if she’d responded. I don’t know why, but I was almost timid, hoping that she’d liked my message.

Shortly thereafter, I received another message from her: “are you experienced with discrete hookups? This would be my first.”

In response, I told her a bit more about myself and some of my sexual history. Between long term relationships, I’d often served as a bull with a few hotwife and cuckold couples in the area. In a few instances, I’d even played with the husbands while the wife watched and helped.

As soon as I mentioned bi contact with husbands, TightLips immediately perked up and kept asking me questions on the subject.

Over the course of the day, our messages became more and more frequent, as we slowly shared our sexual histories and our fantasies. That evening, after I described being with a married woman the year before, Tightlips wrote: “You won’t believe this, but I’m soaking wet.”

In response, I wrote: “Can I see?”

Tightlips responded: “Yes, but no face.”

Reddit chat doesn’t support photos, and we quickly moved our discussion over to Kik.

Within a few moments, I received a photo notification through Kik. With a bit of excitement, I opened it up. Suddenly, my phone’s screen was filled with a beautiful pink pussy, with tight lips and small tuft of light brown hair above her clit. From reflecting light, it was easy to see that she was soaking wet, a small puddle of pussy juice and grool down towards her ass. She’d pulled her panties to the side to take the photo, and it was clear from the wet fabric that she’d been wet for some time. The light colored fabric was dark with pussy juice.

Staring at the photo, my hands trembled a bit and my mouth watered at the sight. Sitting on the couch, I struggled to resist stroking my cock, my erection straining against my sweatpants.

My phone chimed again: “Your turn” she said.

Pulling down my sweatpants, my cock quickly sprung out. I kept things pretty closely shaved, but it looked pretty good tonight. I am circumcised and about 7.5 inches on a good day. My balls tend to hang pretty low, especially with the Summer heat.

Placing my hand around the base of my cock, I took a photo. Looking at it, there was a big drop of precum leaking out of the head. Hoping that she’d like it, I pushed send.

Almost immediately, she responded: “I need to taste and feel that. You look amazing.”

Before signing off for the evening, I asked her “what can I call you?”

“Call me Kelly.”

Lying in bed that evening, I couldn’t think about anything other than Kelly. At least a few times, I opened up my phone just to look at that gorgeous pussy again. I fought the urge to stroke my cock, hoping that I’d get the chance to meet her in the next week or so, and wanting to save my cum for her. Despite my persistent erection, I eventually managed to fall asleep.

The next morning, I woke up to another phone notification, and another photo. This time, Tracy had sent me a photo of her toned thighs right after she had stepped out of the shower. Her legs looked athletic and toned, with a nice copper tan. She was barefoot, but I could see her toes had been painted with French tips. I’d never really noticed a woman’s feet before, but everything about this photo drove me wild.

I response, I took a shower and then took my own photo. I made sure to flex my quads and calves a bit, showing off my athletic cyclist’s physique.

Throughout the day, we continued to share messages with increasing frequency. Almost every other hour, I’d receive a photo notification from Kelly, slowly revealing more and more of her nude body. In a few photos, it was clear that Kelly was at work and taking photos in the office bathroom. My cock throbbed at the thought of this cute woman, stripping off her clothes and being an slut in the office for me.

As we continued chatting, we ran out of casual and anonymous topics to discuss, and started planning the details of a hypothetical meeting between us. Kelly was very concerned about protecting her anonymity, and asked whether I’d let her wear a small black lace mask over her eyes. “Absolutely” I said, “I want you to be totally comfortable.”

I told her that I’d rent a hotel room, and that she could simply visit and have a drink with me. I told Kelly that if she wanted to take it further, that was entirely up to her. As the days went by, I could feel her get more and more excited. She even sent me a photo of a dark blue cocktail dress and black heels, which she planned on wearing.

Finally, she asked “when are we doing this?”

“Friday night, three days from now.” I responded. “Fairmont Hotel, downtown. 8:30, I’ll send you the room number that night.”

“I have one more request though” I said.

“What’s that?” she responded.

“I’d like to see a full length shot of you, as much as your willing to share.”

After pushing send, I could see that she had read my message, but she wasn’t typing a response. I worried that I’d overstepped the bounds until “ding” and a photo came through.

In the photo was a beautiful woman with light-brown hair and an athletic figure but thick thighs and a few curves. Her natural breasts were gorgeous, dark areola with blue and red veins showing through her pale skin. From the photo, Kelly had the tan-lines left by a pretty conservative one-piece swimsuit. As my eyes moved lower, I could see that she’d shaved all of her pubic hair off and that her pussy lips were peaking out. Cleverly, Kelly had positioned her phone so that it covered her face, protecting her anonymity.

As I examined her beautiful photo, I suddenly noticed another photo hanging in the background in Kelly’s master bathroom. It was a panoramic photo of Lake Tahoe, taken from the chairlift at Heavenly ski resort. I knew the subject well, because I had taken that exact photo three years before. I had also given a copy of that photo to my older sister Tanya and her husband as a Christmas gift.

As the realization washed over me like a wave, my heart nearly burst out of my chest. Here I was, cock in hand, staring at my sister’s beautiful nude figure on my phone. I didn’t know how to react, the loud sound of my pulse in my ears, my chest heaving as I tried to control the adrenaline.

My mind raced “should I tell her…Should I say something…will it ruin our relationship forever?”

I could barely move for ten minutes as I considered these questions and the morality of what I should do. Suddenly, another message popped up:

“Did you like it?” Kelly (Tanya) asked.

“I love it.” I responded.

“Good, because I’m looking forward to feeling your hands on my body and your cock inside me Friday night. Get a good sleep.”

With that, I set my phone down. My hands still shaking.

“Would I fuck my own sister? Would she even want to fuck me?” I didn’t know the answer, but I had a plan for answering both those questions.

Source: reddit.com/r/eroticliterature/comments/i07jj1/bs_a_familiar_connection_mf_slow_buildup_part_1