I travel a lot for work. It can be fun seeing different cities and different lifestyles, but after you've seen several hundred, they all begin to look the same. And night after night sitting around hotel rooms loses it's glamour after awhile. You see the same movies on pay per view and eat the same food and life becomes routine and dull. After a long day of work in another podunk town, I come into the hotel bar and belly up to the bar. I look around the place and see her. In fact, every guy in the bar sees her. She's dressed very nicely in a very conservative skirt, blouse & jacket. Her dark hair is all business - pulled back in a pony-tail. She looks so prim and proper - like a "goody two shoes."
All of the guys are trying to buy her drinks & talk. And all of them are failing in their attempts. It seems that I'm the only one in the place, that's there to have a drink & wind down. She can overhear some of my conversation with the bartender & can tell I'm the kind of guy that enjoys a good talk. I'm not hitting on any of the women, just little chit chat with the bartender. Well, she comes over and sits down next to me. She apologizes, but says she would like to "use" me. She tells me that if the other guys see her sitting with me - they will leave her alone.
We talk & talk -- about everything & nothing. I tell her that I'm married and she says she is too and that seems to make us both feel a bit more comfortable. After telling our life stories, our discussion migrates towards sex. Just general things: turn-ons, turn-offs. It isn't erotic talk - more like a sex help show. Somewhere in the conversation, I tell her about my wife & I having "mutual masturbation" sessions. During these times, we lay in bed, with the lights on and start touching ourselves. Our goal isn't to make ourselves cum, but to do things that will make the other person cum. We aren't allowed to touch the other person (until we both orgasm and we start up the 2nd session of the night). I also tell her that when I'm on the road, I don't sleep that well & that I usually have to masturbate before I can fall a sleep. Well, we talk until past midnite & decide that the night has to end. During our conversation I have concluded that she is definitely not the "goody two shoes" that I original thought.
As we are parting, I make a comment that its good we're leaving now because "I need some time in the room to 'unwind' before I can fall asleep." She remembers from our conversation what I'm referring to. She seems amazed that I said that & turns a little red - but I can see she's trying to figure out if I'm telling the truth or making a joke. She knows I'm married, so she know I'm not expecting anything from her. While a part of her finds it kind of repulsive -- the thought of a guy sitting there with a hand full of lotion stroking his hard cock, grunting and groaning, trying to get himself off -- deep inside, there's a part of her that is excited by the thought of watching this. She asks if I'm serious? I'm not ashamed & tell her that I am totally serious.
Now she's really intrigued and asks if she could watch me while I do it. I figure she's just teasing me, so I say "sure, come on along." She follows me to my hotel room & when we get there, she surprises me by actually going in. Well, now I'm getting nervous because I didn't really think she'd go through with this. I order a bottle of wine from room service (trying to see if she's really going to leave) but, she stays. I change out of my suit & into my pajamas (which are really just shorts & a tee shirt).
The wine shows up & we each have some wine. Just enough to relax the situation. I'm really nervous because I've never done this in front of anyone before (except my wife) but, the wine is helping. I take off my clothes and lay back on the bed. She takes a seat in a arm chair facing me. She can see that I'm swelling up, but I'm not really hard. I start by rubbing my thighs & running my fingers all along the length of my cock and across the head. Slowly it turns into a massage, rubbing the palm of my hand on my cock and fondling my balls. Every once in while, I wrap my hand around the shaft, give it a squeeze or a few strokes. This continues for a few minutes and she notices that I'm still not getting totally hard.
She asks if there's anything wrong. I ask her if she would mind at least taking her jacket off, because she looks like that "goody two shoes" again. It makes me feel like I'm jerking off with my sister watching. She surprises me by not only taking her jacket off, but asks if she can have one of my dress shirts. She turns her back to me and removes everything but her panties and pulls on my dress shirt. She tried to be coy by turning her back, but didn't realize that I can see her front in the room's mirror. Not a tan line on her body! She is slim but not skinny. Small pert breasts and dark brown nipples and areolas. She had not yet buttoned up the shirt and stretched her arms back to remove the pony-tail. Her hair falls down onto her shoulders and around her face as she buttons up the shirt. She looks incredibly sexy and I totally change my mind about the goody two shoes thing. She takes her seat in the chair again sitting right across from me.
I immediately get totally hard. She notices this and it gets her tingly and she can feel herself getting wet. As she watches me stroke my cock, she can't help but run her hands across her own body. I tell her" "if want to play with yourself that would be OK." I reason that my wife can't be upset, because the only difference between this and a chat room is that we're in the same room. We're still just doing this to ourselves. "My wife won't mind" I keep saying over & over to myself. I'm going to tell my wife about this, but I'm not planning on telling her we were in the same room together - that we chatted on-line. After a little more stroking, I convince her to try it. She runs her hand over her breasts and swings one of her legs over the arm of the chair. One of her hands goes inside her shirt - while the other is inching down to the top of her panties. One finger is slowing making its way under the waist band toward her moist pussy.
