Maggie Introduction

Men are strange. Some stranger that others. Some men want to show off their women (wives, girlfriends, mistresses, whatever) to arouse envy. Some want to test the loyalty of "their" women by suggesting to other men that "their" woman is available. In this case, if the woman succumbs to the desires of another man, she fails the test. Still other men harbour a fantasy (explicitly held or not) of being cuckolded, becoming aroused at the idea or the fact "their" woman being intimate with another.

I don't know for certain which category he fell into, but Maggie's boyfriend seemed pretty desperate for me to meet her, even if only online (separate continents). Maggie was unsure, but because I was older, and thus merited a display of respect accorded an elder, and because her boyfriend really seemed to want it, she agreed to chat with me.

She was by turns shy, sweet, nervous, and engaging. Maggie let it be known she deeply loved her boyfriend, and that she was his. We chatted about her goals, dreams, her family, her relationship with her boyfriend. It was a pleasant chat, with no overtones of what was eventually to come.

Maggie comes from a conservative family, and gave the impression of being a very modest woman. Her boyfriend seemed more cosmopolitan, and Maggie and I eventually chatted about how that clash impacted the physical aspects of her relationship with her boyfriend. Hesitantly, she acknowledged that she was a virgin, but that she and her boyfriend has experimented. The experimentation was rather constrained, as she admitted she'd received, but not given, oral. Whether her limited experience was attributable to her conservative family or inherent modesty, she was delightfully innocent.

Her boyfriend had told me that Maggie just didn't do pictures. He didn't mean nudes. He meant that Maggie would likely never willingly give me a picture of herself. She'd probably always be an enigma, words on a screen, as far as I was concerned. So of course, this was the first point I tested. After a small number of chats, I prevailed upon her to share a photo. What I received was a picture of a very pretty young woman, with a tentative smile, and a positively delicious form.

When Maggie asked what I thought of her, I told the truth. That she was pretty, and very attractive. She was surprised I'd say that to her face (so to speak). I told her there was more to be said, but I didn't know if she'd be comfortable hearing. She was shy, but wanted to hear what I had to say. I explained how I wanted to touch her, given the chance, what I would do with her. She was shocked, and for a little while it seemed she might stop speaking with me.

She told me she was torn. She deeply loved her boyfriend, but she was, much to her confusion, drawn to this strange older man. She wanted to understand more about what I meant, and began to come to chat with timid question about, for example, what doggy was, and why some older men like to be called Daddy by younger women. She also worried that my knowledge of her undying affection for her boyfriend would make me withdraw, as if my knowing that she'd never leave him would have conclude she'd never submit to me fully - my words not hers.

However, in the end, her curiosity, or suppressed sexuality, won out and she wanted to know more. Our visits often became explicitly sexual in nature. I explained how I would touch her, instructing her to touch herself in keeping with my words. Hesitant at first, she became more compliant, more willing to explore. And far from her boyfriend's prediction, she began to send pictures of herself. Clothed, yes, but images that none-the-less conveyed sensuality and a sexual hunger just below the surface.

Once, she sent a picture wearing clothes that revealed her thighs. What beautiful legs she has. She was simultaneously mortified and aroused at her audacity. We spoke more about how an older man might use a younger woman to their mutual pleasure, and acted on those conversations in our virtual bubble.

One night, as I described what I'd do with her, she obeyed my instructions and masturbated to orgasm. She commented on how wet she was, how aroused, and I insisted she show me how wet her fingers were. A delightful glistening web of desire stretched between her fingers. How I wanted to taste them, and the source of the desire between her legs.

We discussed making a point to meet. She reminded me that she'd never leave her boyfriend, but that she would submit to me because I was older, humble, and deserved respect. The chats about meeting up led to orgasms and more, modest, photos. Though out, Maggie's shyness came through in her use of abbreviations. "F me please" "my p is wet" "is your c hard" were all Maggie's preferred way to "talk dirty."

We separated for a bit. Circumstances were such that we could not continue. She never left my mind, nor, apparently, did I leave hers. I missed her, and it turns out she missed me. She found her way back to me after an interval of time. Her boyfriend had moved away, and she was feeling alone. She said they were together, but had broken up. Their relationship was unclear, in flux. We however quickly regained our rhythm, conversing about life, dreams and, of course, my using her.

I reminded her that I would insist on seeing more of her. Rather than a categorical no, as in the past, Maggie asked that we go slow in that direction, and that she was very nervous. She reminded me that she was from a very conservative background, and what I was requiring was hard. Our first few nights of visiting brought a few modest pictures. One point, after she'd obeyed instructions and had an intense orgasm, she sent a picture of herself wearing a bra. I asked for more, and the next I knew, I was confronted with a beautiful, wild face of woman unlocking a new level of sexual desire, and a glimpse of her breasts.

A few short nights later, Maggie was feeling bold. She threw caution to the wind, following my instructions to eventually wrack her body with several orgasms, all while fully naked. She rode her pillow, then rubbed her pussy, finally fingering herself, cumming with each exercise in self-pleasure.

I reminded her that I had yet to clearly see her breasts. No hesitation this time -- her pert 34B breasts and perfect brown nipples promptly appeared on my screen. "Happy?" She asked. "Happier if I saw your wet pussy too" I replied. The next image was her hips, thighs, and mound. So bold, so daring. Her display stunned her and aroused me.

She reminded me that she still had deep feelings for her boyfriend and that she was only doing this with me because she respected me. No other man would see what I had, no get the obedience and respect that I did from her. And then, in a departure from her usual abbreviated dirty talk, she said she wanted me to fuck her. That she'd do exactly what I said.

True to her word, she followed my directions and had a leg trembling orgasm. I told her that now was the time to share her pussy with me. A mild protest of be nervous was shortly followed by a picture of a dripping wet pussy, with so much cream that it seemed she'd been cream-pied.

Maggie was both proud and shocked by her wanton conduct. This was further than she could have imagined and set the stage for us to plan to meet.