Lynn - Part 1

An intimate dinner, a few probing questions and a rush to her hotel room... I'll call her Lynn. She was 26 years old, long dark hair, big brown eyes, pretty face, petite (about 5'1", if that), slender, with breasts that I guessed to be a B cup (or, perhaps more accurately, an A+). She was a marketing assistant in one of our regional offices and I'd met her casually when I traveled to that location. We'd never exchanged much more than routine pleasantries, no flirting, just brief "office talk." I had noted that she seemed to be what I liked to term "effervescent:" alive, alert, energetic, with a quick smile, personable and friendly. Married or single I didn't know for sure, but I did note the absence of a wedding ring, so I assumed she was single. I, on the other hand was (and still am) married, 42 years old at the time and not exactly a Tom Cruise lookalike. On this particular occasion, Lynn was visiting the home office (my base of operations) to work with me and a couple of other coworkers on a special project. The team put in some very long hours and at the end of the week, we were pretty tired and ready to knock off for the weekend. Lynn was scheduled to fly back home on Saturday. During the week I had gotten to know her a bit better and my initial assumptions about her being fun, lively, personable and friendly were confirmed. I should also mention that in ways that were subtle, yet noticeable, sexy and sexual would also be appropriate adjectives. Maybe even "wild," although this may have been more imagination and fantasy on my part. Still, there seemed to be something, a vibe, a hint, of naughtiness about her. She didn't talk much about her personal life and seemed to prefer to spend the evenings alone in her hotel, having declined offers to join one or another of the team for dinner and drinks. On this, her last night in town, the other members of the team were only too eager to head for home at the earliest opportunity, leaving Lynn and me to wrap up the project. Knowing it was her last night, I offered her a "thank you" dinner and, much to my surprise, she accepted and we soon found ourselves in one of our city's better restaurants, located right in her hotel, sitting fairly close together in a horseshoe-shaped booth. After some minutes of the usual small talk, I steered the conversation to her, asking her about her family, college, interests, etc. She responded willingly and openly and I asked if she were married, involved or single. "Single now," she responded. "I just broke up with my boyfriend a couple of days before coming here...and am not really interested in getting involved with anybody for awhile." I offered my sympathies about her break-up and she offered (having had two drinks, one a Long Island Iced Tea, by this time) that "well, when things are bad both in the bedroom and outside, there's not much reason for keeping it going." I quickly agreed, mentally honing in on her "bedroom" comment, which seemed to be a subtle (and maybe unintentional) opening to explore this subject further. "So now you're sleeping alone and liking it better?" I asked, attempting to convey with my tone and manner that such a question was just part of casual conversation. "Well," she responded, with what can only be described as an "impish" smile, "you don't always need a partner to have good sex, right?" It was an effort, but I managed to avoid spilling my drink as she said this. At that moment, our dinner arrived and the conversation was momentarily interrupted. But only momentarily; I wasn't about to let this opportunity (if it was an opportunity) pass unremarked. "That's true," I said with a smile, "sometimes it's even better without a partner." "Definitely!" she responded, laughing, "and you don't have to worry about if he's in the mood or able to do it...if you know what I mean...especially if he gets jealous or whatever when you just go ahead and do it yourself." I hadn't expected such openness, such candor (and maybe some teasing as well?) and the increasing tightness in my slacks indicated that her words were having an impact beyond the merely conversational. Continuing my attempts not to show my prurience and arousal, I chewed a mouthful of food for a few moments before responding. "Well, a lot of guys would consider it a turn-on, not something to be jealous about. A lot of women aren't so open about it." "Yeah, I know," she said, "it's really kinda silly that something we all do is considered to be some kind of big taboo or something, but I know what you mean about women - and guys, too - being freaked out about the subject." "Well, I must say, I'm glad you're not...if you don't mind my saying so, I'm rather enjoying this conversation." A sexy smile was her only response and I decided to continue. "And I must admit that I'm kinda curious..." "Oh, yeah? About what?" The tone of her voice conveyed an invitation, a tease, even a dare. She was now on her third drink (a margarita this time) and it was obvious that the alcohol was fueling her lack of (verbal) inhibitions. I waited a few moments, not wanting to seem too eager (although the swelling in my pants was getting increasingly difficult to ignore). "Well, OK, here's a question: how often do you do it?" Her smile was absolutely devilish as she answered...and evaded. "Somehow I knew you were going to ask that. So what is it you want to know, how often I masturbate?" She knew damned well what I wanted to know and knew that I knew that she was teasing me. "And if I tell you," she continued, "are you going to tell me?" Just hearing her say the word "masturbate," was as if I had been suddenly given a large dose of testosterone, IV. For several seconds I was, quite literally, unable to answer (perhaps because my tongue was hard?). Eventually, I was able to respond with some coherence: "Fair is fair, you tell me, I'll tell you." Now it seemed as though it was Lynn who was a bit tongue-tied. She was actually blushing and hesitating, not looking directly at me, as if pondering whether to respond, knowing that this conversation could very easily lead to more than just talk. After what seemed like minutes of silence, she looked up, took a deep breath and answered. "Well, this is kind of embarrassing...I mean, I've never really talked this openly about it before, at least not with a guy I'm not involved with." Again, the hesitation, the silence. I, too, was silent, deliberately so, my non-response an unspoken challenge for her to continue. A long swallow of her drink, then: "OK, if you really want to know...at least once a day, sometimes more, depending if I'm seeing someone or not...and sometimes even then. I mean, when I feel like doing it, I just do it. It's really no big deal. Now how about you? How often do you do it? I mean, you're married, right?, so probably not all that often, right?" Her teasing and inviting smile was back, her cheeks still red and I could see a deep pink flush on her upper chest (she was wearing some kind of scoop-neck shirt and slacks). Obviously, I wasn't the only one getting turned-on by this conversation. "Actually," I answered, I do it almost as often as you do. My wife and I only have sex a couple of times a week, if that, so I'm a 'do-it-yourselfer' the rest of the time." (I felt that I needed to be as candid as she was if I wanted the conversation to continue - as well as maybe, just maybe, progress to more than just talk). "Really?" she responded. "I would've thought maybe not as much...but then, like I said, it's no big deal." Wanting to keep the conversation focused and moving right along, I quickly asked: "Ready for the next question?" "Go for it." "How about last night...did ya do it then?" "What d'you think?" Again, the laugh, the implicit tease. "I think 'definitely'" I told her. "And how about today...?" "Oh, yeah, like I had time today. We hardly had time to pee, let alone anything else." She paused, then asked, "So how about you? Did you do anything last night?" "No, dammit. I was too tired to do anything, which is pretty unusual. So," I continued, "I guess that means that tonight we'll both be busy, right?" "Ya think?!" She answered, leering. "Well, I gotta tell ya, after this conversation there's no way I could NOT..." I hesitated, unsure of whether to be really explicit, then, perhaps helped by my drinks (it wasn't only Lynn who was enjoying the bartender's expertise)..."jack-off." "Oh, god, this conversation is such a turn-on," was her response. "Tell me about it; I don't think I could stand up without tipping the table over," I told her. "Yeah, well I probably look like I wet my pants..." She looked at me, expectantly, as if wanting me to take the conversation to the next level (whereever that might be). "You're lucky, your room is right upstairs. I've got at least a 30 minute drive home." I paused..."or...well..." I paused again. "Or well what?...Are you thinking what I'm thinking?" Damn, she did have a talent for saying while not saying. "Maybe..." was my feeble and equally evasive response. "Maybe what? Go ahead and say what you wanna say," Lynn urged. "Do you like to watch? I mean like do it with someone, together?" There, I said it. Not precisely direct, but direct enough. "Omigawd...I sure hope you don't think I do this all the time...but, yes, I like that...a lot. Watching and doing it together, I mean." Her voice was husky, low, her breathing markedly faster, her tone of voice conveying an invitation. "How about tonight?" I asked, my heart pounding so hard I'm sure she could've heard it. This was the "moment of truth," a bit bold on my part, but nothing ventured, nothing gained. And my intuition told me that she wouldn't decline. Or would she? Maybe I was a bit too bold, a bit premature. But a hard cock tends to cloud judgment and what was said was said. I was literally trembling, waiting for her answer. At that very moment the waiter appeared, asked if there was anything else and left the check. To say my pulse was racing would be an understatement. Lynn grabbed the check, signed it to her room, quickly scribbling her name, stood up and grabbed me by the hand. "Let's go right now before I change my mind," she virtually commanded. I needed no urging and we literally ran to the elevator. Continued