When my 28[F] lingerie blog led to a week of fucking an older man 40[M] in Boston. [PART 1]

It was June of 2018. The month had been uneventful and was coming to a close. It was a lazy morning, and I absentmindedly opened my Tumblr blog and typed ‘men in suits’ while I slowly slid my pajama pants down my legs. Tumblr was my go-to when it was time to touch myself, and I had a fantasy of being a slut for a successful older business man. A listing of blogs came up. One, I noticed, had a profile photo that caught my eye… A man in a brown suit, just from the shoulders down, adjusting his cuffs. I clicked to his page. His bio told me his name was Drew, and he was 12 years older than me. A reblogged gif of a woman getting sensually fucked with a hand around her thiroat was the first image. My fingers found my clit. I hit the follow button.

Two days later, I got a message.

“Hi there. Thanks for the follow!”

“Of course! :)”, I replied. Shortly after, a follow back came through, as well as methodical likes on my posts. I could tell he was making his way down my page. My blog was a passion project of posts of me – lingerie, silhouettes, nudity… Far classier than what now resides on my reddit profile. But, then again, I like to think that sensuality still shows through.

A few hours later, another notification appeared. “How is your week going?” Small talk. Actually…appreciated. When you’re a woman that posts her naked body on the internet, there’s no shortage of men diving into your inbox to describe what they’d like to do to you. It becomes repetitive. Sometimes, even boring. But this… the restraint and normalcy, even when I knew he was staring at my lace-clad tits… I loved it. I responded, and our first conversation was born.

At first, we talked about innocuous subjects I still love to this day. The typicals of the weather in California, where neither of us lived. The joys of Excel spreadsheets and formulas. The Employment Lawyer at work that had given a sexual harassment prevention training and followed it up with a LinkedIn message telling me how good my ass looked in my jeans. Despite the opportunities, the conversation never went sexual, but was ripe with sensual tension. Have you ever gotten turned on talking about v-lookups? I have.

Shortly after we began talking, I left to spend 9 days solo thru-hiking a section of the Appalachian Trail. He knew I was headed hiking, but not much more. I let him know I’d check in every now and then to assure him I wasn’t murdered or eaten by bears, but service would be slim. He told me later that he thought it was just some coy way of shutting him down and ending the conversation. ‘She didn’t message me back? Well, makes sense, she’s walking in the woods for eternity.’ It wasn’t the case. In the woods, I was thinking about him. After two days and 43 miles of hiking, I got cell service. I texted my family first, and thought about sending a message. But… for some reason, I held back. I just told the man I’d be gone for 9 days. 48 hours seemed too soon. I posted a photo of my naked legs (and ass) on my page, appreciating them for carrying me 42 miles thus far, and he messaged me the next morning.

“Hey! How’s it going so far?”

Seeing his message made me giddy. I filled him in on my trip – my 31 mile first day due to a creepy guy at a shelter, my 12 mile hike to the next stop with a shitty blister, my eagerness to keep going… It was exciting to share. We kept in touch every few days as I kept going, finding cell signals here and there in the peaks and valleys. Half way through my trip, I was running down a trail and almost landed on a four foot rattlesnake. As I internally screamed loud enough to wake the corpse of Helen Keller, I slowly backed down the trail and let the snake pass. Immediately, I whipped out my phone, took a photo, and sent it to Drew.

“Well, 10.5 miles in today and just almost stepped on a four foot long rattlesnake. Or as we call them in the trail running world, danger noodles.”

“Jesus woman”, Drew responded. He would later tell me that this was the moment that made him certain he was enthralled with me. That he told himself he couldn’t screw this one up. I had never anticipated ‘danger noodles’ to become my most successful unintended pick-up line.

When my hike finished, it became normal for us to chat on and off throughout an entire day. Our conversation became increasingly flirtatious and filled with sexual innuendo. We were driving each other crazy by not just jumping in, and we both loved it. Have you ever been edged emotionally? God, it’s fucking amazing.

Eventually, it happened. We talked about what it would feel like to run our hands down each other. We talked about his cock and how thick he was, and my reputation for being a bit of a small crawlspace rather than a hallway. I wanted him so badly. Our video calls became frequent and increasingly sexual until we were masturbating with each other. The thought of touching him for real was electric in my brain.

A few months later, I had a conference to attend in Boston. “What a surprise!” Drew shared. “I’m supposed to be in Boston that same week!”

Drew was not, in fact, supposed to be in Boston that week. In fact, the reason he said he needed to be there – to review a building being built – wasn’t being built at all, and isn’t even planned to start being built until 2021. I caught on immediately that he had no reason to be in town other than me, and played coy to go along with it. I wanted him.

That week, I made it to Boston first. Before he left, I’d made an offer for him to cancel his hotel room. I’d gotten a nice B&B room in a beautiful part of town, paid for by my company. It had a big bed, so why not? “We’ll be hanging out a lot anyway, so even if we’re just friends, it’ll be fun!”

There was no fucking way I was going to let this be just friends.

Drew flew in the next day. I dressed as sexy as one can when attending a professional conference – a tight dress and heels that apparently made an impression, as the President of one of the Screen Actors Guild divisions asked for my number during the conference. I turned him down. Me, a woman with a successful older business man fantasy. That’s how committed I was.

The conference was almost over when Drew messaged. “I just got to the hotel room. Dropping off my stuff and I’m on my way over to you.” I ran to the bathroom to make sure I still looked as good as I thought I did. Jesus christ I was wet. Was I supposed to be this wet? I felt like I was trying to open the next SeaWorld franchise. I left the bathroom with my wetness making my thighs slick under my dress.

My phone buzzed. “I’m here”. I was on the third floor, and assumed he’d be waiting in the lobby. But, as I got on the escalator, I saw him at the bottom about to head up to me. We locked eyes and froze for a second. We were both real. We were both here. He made a joking motion to get on the up escalator as I was coming down. It broke the ice, and we both laughed. I got to the bottom and immediately hugged him. He felt exactly as I had hoped. As we walked to the next escalator together and stepped on, I put my hand on his back. Just that touch made me gush even more.

To get descriptions out of the way, well… You can see me. I’m a 5’11” athletic woman with bright blue eyes and a pretty great ass. At this time, I had a pixie cut I spiked up into a faux hawk. Drew was a typical 6″2′, 40 year old business man with a dad bod midsection and athletic legs. With my heels on, we were eye level.

We left the lobby and started walking the streets back to our room. We’d made a promise before we got there – our clothes stayed on until after dinner for three reasons: 1. We both loved edging and denial, and making us both wait even longer for what we knew was coming was so fucking hot; 2. We knew that as soon as our clothes came off they weren’t going back on until the morning; and 3. We were in fucking Boston. You HAVE to get good food. Our walk back felt like asking your crush out in middle school. We were both giddy and high on life. I kept turning to look at him just a little too long and almost ate shit on the sidewalk. Our fingers brushed past each other as we walked closely, neither of us knowing if we should take the other’s hand. Once we got inside the room, we both sat down on the couch together, me closely against his side and his arm around me. Do you remember in high school when you didn’t know what to do with a date, so you’d show them random things in your room? Well… We did that with our phones like two teenagers unsure of who should make the first move. As we sat and talked, our faces got closer and closer until I couldn’t take it anymore. I put my fingers lightly against his cheek, leaned in, and put my lips against his.

That moment felt like it lasted forever. We couldn’t stop. I straddled him, sliding my dress up to just below my ass. He didn’t know yet, but I hadn’t worn panties, so, without thinking, my wet pussy was directly against his khakis. I ground my hips into him, desperate to feel his hard cock through his pants. His hands slid under my dress and pulled my ass towards him. We both moaned into each other as the passion of the past few months almost overtook us.

I was the one that broke the kiss first and leaned back. “So, uh… We have a decision to make.” I leaned in to his ear and softened my voice. He could feel my breath against his neck. “We can stop right now and go get that dinner and drink we have planned, or we can take our clothes off and you can fuck me on this couch.” He paused, looked in my eyes and said, “…Are you hungry?” Me, being the tease I am, said yes with a wink. I slowly crawled off of him, revealing the puddle I’d left on his lap. He still hadn’t realized I wasn’t wearing panties. “Oops”, I said. Seaworld had found a new location.

Drew changed his pants and we went for dinner in town. We ended up at a swanky bar with sexy waitresses. I sat against the side of Drew and whispered in his ear how hot it would be if he watched me fuck one of them. “Just so you know,” I said “I’m not wearing any panties”. His eyes went wide, he got rock hard, and it led to us making out in the middle of the bar with my hand touching his cock through his jeans. The waitresses watched. I loved the feeling of being the hot young girl all over her older guy. We agreed we couldn’t fuck in the bar, so we paid out tab and left, slowly walking back to the room while our hands continued to run all over each other. The tease had been long enough, and I couldn’t fucking wait.

Source: reddit.com/r/gonewildstories/comments/kg8agy/when_my_28f_lingerie_blog_led_to_a_week_of