Author: JennAnon

The “Lay”over Pt 1 [Fm]

Two full days of meetings, drinks, and meals was finally coming to an end. I was at my final dinner meeting with my new boss and some team leaders anxiously waiting for a text from Tim that he had landed. Fortunately, my hotel wasn’t that far from the restaurant and I was able to go back between work and dinner and freshen up and put on the lingerie that he had bought me.

My watched vibrated and without looking, I excused myself to the ladies room. Tim had just landed and was heading to the hotel and was going to shower. He told me that if I was able to escape dinner, to join him in the shower. I told him that I would do my best and returned to the table. Read more »

Waiting for the “Lay”over [F]

It had been weeks since Tim and I had been together, and we were finally going to meet up for a night. I was flying out to the west coast to meet my new director and team for a series of meetings, drinks, and dinners. Tim was traveling and scheduled a layover for an evening, before heading back out in the morning.

I landed late Sunday evening and headed to the hotel. Tim had booked me a room and I told my firm that I was staying with a friend. I checked in and the concierge handed me a FedEx box, not thinking about it, I went up to my room and took a shower. During the shower, it dawned on me that my company didn’t know where I was staying and the box was from Tim. I quickly finished wrapped myself in a towel and tore into the box. He had bought me some sexy lingerie with a note “I can’t wait to see you in this and out of it”. I immediately tried it on and got turned on looking at myself in the mirror and thinking of what he was going to be doing to me. Read more »

Role Play to Reality (3) – Wake Up !! [FM]

Part Two
https://old.reddit.com/r/gonewildstories/comments/bnep4i/role_play_to_reality_round_2_fm/

I woke up to Jake talking on the phone. I watched him pace back and forth yammering away to his boss. He looked at me and gave me the “one-minute” finger and went back to pacing. I grabbed my phone and saw a LinkedIn notification. Tim **** from **** Co in CA wants to connect. I accepted his request. When Jake finally got off the phone, he told me that he had a change of plans and was meeting with this “super big” client for lunch and he’d meet me at the airport. He was racing around the room getting dressed and throwing his stuff in his suitcase. He went on to tell me about the meeting and then he told me about the game he watched last night with our alma mater winning in the last minute. I snapped back about him being tired. He said he was tired and didn’t want to deal with my little fantasy bs, so he chilled. He then “told” me it would be great if could take his wheelie to the airport and I responded that he’s a big travelling businessman and if he leaves it in the room, it’s gonna stay in the room. He didn’t even apologize as he walked to the door and told me we can discuss this tonight. Read more »

Role Play to Reality – Round 2 [FM]

Part One

https://old.reddit.com/r/gonewildstories/comments/bn6hh4/role_play_to_reality_fm_long/

I woke up to an empty bed. The lights were off in the bedroom and I looked out to the living room to see Tim on the couch in a robe looking at his phone. He looked up, smiled, and greeted me. He then told me that I had been asleep for about an hour. I got out of bed and went to the bathroom peed and wiped myself with a warm face cloth. I walked out the living room and checked my phone in my purse. No messages, calls, or emails. I slid it back into my purse and walked over to the couch. Tim offered me a robe and I declined as I snuggled up next to him on the couch. He told me that he was getting caught up on emails. I jokingly asked how many pictures he took of me when I was asleep. He showed me his camera roll and I told him I was offended that there was not even one. He laughed as I leaned in to kiss him. We kissed for a while, then I slide my hand in his robe and began gently rubbing his hardening cock. I untied and opened his robe and began kissing his chest working my way down. I started licking his shaft and could taste the remnants of our sex. I was getting turned on. I began sucking his cock and Tim fondled my breasts. His hand then slid down and he began playing with my pussy and I spread my legs to give him more access. I was immediately getting turned on and began moaning with his cock in my mouth. I came up for air panting and then went back to devouring his cock. He placed his hand on my head and I moaned as his hips gently thrusted his cock deeper into my mouth. His finger was probing my pussy and it was dripping wet. I finally separated and climbed on top of him and slip him inside of me. I began working him slowly inside of me as he sucked on my breasts. His hands were grabbing my ass and would occasionally come up and kiss me. Read more »

Role Play to Reality [FM] (Long)

My boyfriend Jake had a business trip down south and I decided to take a few days off and relax in the sun while he networked and played golf. I arrived late Thursday night and planned to spend Friday and Saturday with him, but it being a business trip, he had booked himself solid through the weekend and left only Saturday night for me.

So, Saturday night comes and Jake arrives back at the hotel tired from drinking and golf and wanted to hang out for the evening and order room service. I was like a caged animal and wanted to go out. I had been very forward with him about going out and he had promised. We had talked about spicing up our sex life. We tried light bondage, I bought a vibrator, which I think intimidates him, and we talk about role playing. He wanted to do the naughty school girl/professor and I wanted him to pick me up in a bar. I told him that I didn’t even need dinner, I just wanted him to pick me up at the bar and have his way with me that night. After going back and forth for a few minutes, he finally relented and agreed to doing the role play. Read more »