I hate traveling for work. What I do can be done remotely. I'm the guy relaxing at the coffee shop, or the library, sitting in the mall, anywhere I have a decent wifi connection and I'm good. On rare occasions I have to travel onsite and it sucks. This particular time was a favor for a friend. He had too much on his plate to do the job so it fell to me. Kiss the wife, hug the kids, off I go to San Diego.
The whole flight I kept starring at the letterhead on the proposal. I could swear I knew the logo, knew the name of the firm, but couldn't place it. Even when I made it to SD I couldn't quite figure out how I knew that firm. Hotel didn't do early checkin, no big deal it's a roller an a backpack I can manage. I debated about renting a car an then just hailed a cab. The firm was massive, huge lobby, hot receptionist. She took my name and told me it'd be a moment.
It wasn't until I heard the click of the heels, the gasp, and the soft voice that it clicked and I knew why the name was familiar. Standing behind me was my ex from high school. Yay awkward professional environment. She found out that morning that I'd be the one handling the job. Her boss assigned her as my babysitter while I was here. Jane didn't think it was funny, her boss probably did. Jane offered a tour of the place. I asked where I could leave my bags and the receptionist stashed them for me. I kept pace so I wouldn't stare at Jane's ass. She'd grown from the high school girl into a beautiful woman. I noticed the ring, lucky guy. She rattled off about this office or that person and I just nodded and kept going. I was here to fix the system, everything else was a distraction.
After the tour I offered to buy Jane lunch. I admitted I'd taken a cab and that I hadn't checked in yet. Just to make it overly awkward I threw in "not a date" and the smile on her face said I'd hit my mark. I was fine with taking a cab but she offered to drive. We picked up the bags and headed to some Thai place. Lunch was great. Conversation was all business until that ran out. Then things went personal. I was married, I had kids. She was married, had a little girl. We stayed away from the "since high school" cliche. I think both of us wanted to avoid talking about that part. Eventually I picked up the check. Again I offered to get a cab so as not to inconvenience her. She insisted on dropping me off at the hotel.
It was in the hotel parking lot where I sensed something was wrong. Instead of just dropping me off she parked on the side. She seemed distracted and suddenly started sobbing. She'd caught her husband Brad cheating 2 weeks ago. They were not separated. Her daughter was up with her parents for the summer and she really didn't want to go home to an empty house. I was the shoulder to cry on and I let her sob it out. I offered dinner plans and asked if she wanted to share the room. Room was already booked. She smiled and asked if I'd rather stay at her house. I started to talk about the cancellation policy and she laughed. The firm did a lot of business with this hotel, she could fix it with a single call. Hearing her laugh made me feel better. I hadn't realized we were holding hands, but I did notice her hand on my thigh. She rubbed a little bit and smiled. I didn't fight it and pretty soon my pants were unzipped.
She had her phone in one hand and my cock in her other hand. I could hear the lady's standard hotel greeting. Jane rattled off her friend's name and the lady said it'd be a moment. Jane smiled and started sucking. When her friend came on the line she popped off and started jerking me hard. She told her friend she needed to cancel the room. When the friend started talking she popped back on. 20 minutes of off and on and me having to be as quiet as possible. Once Jane hung up she worked her magic. She knew how close I was, and she didn't care. It felt amazing to drain my balls in her mouth. She stayed on a few moments longer and sucked me dry, swallowing every last drop. I tried not to laugh when she said "hope you wife doesn't mind I borrowed you".
