I was planning to be in Philadelphia on business and on a whim decided to post in Reddit for some company. After regular travel, the hotels and chain restaurants all feel the same and having someone to hang out with makes it much more bearable. To my surprise, Emma messaged me back. She was also on a business trip and looking for a similar connection.
First a little about me, I’m early 30’s guy, 5’10, 160 pounds. I stay healthy but don’t have that 6-days-a-week-at-the-gym body. Before our trips Emma and I exchanged messages. She was 5’1, early 20s, and pleasingly curvy. Dark brown hair, and even with her eyes that seemed to say “fuck me please” she had an innocent look to her.
She had recently finished college and was focused on her career. In college she didn’t do much dating and now with her busy life she rarely crossed paths with anyone she found attractive. Her first boyfriend lived across the hall of her freshman dorm and since they broke up during her sophomore year, it’s been just her and a vibrator. After more messages were exchanged she confessed that due to struggles with anxiety she wasn’t looking for PIV sex but instead wanted to comfortably explore a new body and feel warm hands touching her.
We made a plan. She would meet me in the bar at my hotel, we’d chat, and if we clicked, she’d come up to my room. Then, we would take turns. I would tell her how’d I’d like to be touched, she would decide if it was something she was comfortable doing, and if so, the fun would commence. We would continue switching back and forth until we were too tired to continue.
I had an extra hard time sleeping on my flight to Philadelphia. I checked into the hotel and tried my best to focus during the day’s meetings. I was able to sneak out early, take a shower, and rush down to the hotel bar. I was about 30 minutes early but she was already there looking nervous while at the same time sexy in her skirt and a low cut, black top that gave a tempting few of her lightly freckled breasts. The conversation was tame but fun. Talked about work, our frustrations with the moron in the white house, and favorite foods. When our glasses were empty I invited her up and her “yes” sounded like a nervous relief.
The ride up the elevator was awkwardly quiet but once we were in the room with the door closed it all felt more relaxed. I was surprised how nervous I felt when I embraced her, pressing my body against hers. She wrapped her arms around me and let out a tiny sigh. As we kissed I explored her body with my hands. Feeling her warm back and down to her ass. She stepped back an in one motion pulled off her shirt and unclipped her bra exposing her breasts and small, hard nipples.
We fell to the bed and she said that I should first ask her to pleasure me. I quickly agreed, stripped to my boxers, and asked for a massage. It felt amazing. She rubbed my back and my legs. I was hard when I rolled onto my back. She smiled and caressed my thighs. For her turn I gave her a foot massage.
It didn’t take long for the massages to escalate. Per her request I spent about 10 minutes exploring her breasts with my tongue. She gasped and arched her back toward me as my mouth first grazed her nipples.
We were both completely naked when my turn rolled around and I asked her to lick my balls, taint, and (if she was up for it) ass. She smiled as I lay back against some pillows. It felt amazing. Over the course of about 15 minutes she focused completely on my pleasure. Licking my balls, sucking one then the other, drawing circles with her tongue on my taint. I was as hard as I’ve ever been and dripping pre-cum when I felt her tongue press against my asshole. I couldn’t help but moan as she gently pressed her tongue against my sensitive skin.
For her next turn I returned the favor. Exploring her every fold with my mouth, but not yet licking her clit. She looked in agony as she pressed herself towards me, moaning, dripping wet, and begging to cum.
As I put my mouth around her clit and at the same time pressed a finger inside her she immediately came. Moaning and thrusting against me. Her orgasm must have lasted at least 30 seconds and when it finished she lay quivering on the bed. But not to be outdone she quickly changed positions to focus on me.
Starting with my balls in her mouth she placed a hand on my still hard cock. I knew it would only be a short time before I came. Firmly holding the base she lowered her mouth on to me. The warm wetness of her mouth and motion of her tongue quickly pushed me over the edge. As I came she took me further into her mouth swallowing my cum.
The rest of the night continued to be amazing. She had two more orgasms and I had my first prostate orgasm. She ended up sleeping over and more orgasms where shared in the morning. After breakfast I had to check out and fly home. I hope we cross paths again.
Source: reddit.com/r/gonewildstories/comments/8bs9xc/the_most_relaxing_hookup_mf
Great story dude. Sound like an amazing time
Planning to be back in the area? Ever meet up with a couple? You sound like fun
This was super hot! I love a slow, teasing build-up that doesn’t always have to end with piv. Also congrats on the prostate orgasm! I’ve only had one but it’s really unlike any other orgasm I’d ever experienced.
Prostate massages are the best! You sound like you found a winner
How did she get you the prostate orgasm? With fingers? Need details :)