Lee’s Date

Things were fairly tame for most of my life until I met Lee. Things really got a bit wild when I had an experience at a friend’s cabin with her. Lee, my lover, is in her late forties and I in my mid fifties. We very much enjoy our time together. Although we are having an affair and not together officially, we both love each other very much. If I had my way, she’d leave her husband and we’d be together all the time, but I’ve come to the realization that isn’t in the cards for us. She loves her husband too and won’t leave him. In any case, this event occurred awhile ago and is something Lee and I still get worked up about when we talk of it.

Lee arranged to get away from her husband for night, and after telling me I looked to find something special we could do together before we’d go back to my place and make love for what I hoped to be hours. I had it all planed and the day before I’d finally get to see her, I had to go away on business. Of course this happens, except this time we had some tickets to a show that Lee was really looking forward to seeing. After trying to get out of the work trip, I ended up making arrangements for a work buddy Greg, to take Lee, and she was very happy to be going. She’d already made arrangements to get away from her husband so this was going to work out well, even if she and I wouldn’t get to be together.

Greg was a single guy, good looking and 35 years old. Lee had grown to know Greg from the several times that he and I were together when Lee had sneaked away from her husband to come see me. Lee was comfortable with him, they’d flirted a bit here and there and Greg would on occasion, teasingly, tell me in front of Lee how he’d love to have an hour with my gorgeous lady.

I spoke to Lee about an hour before she was leaving to head to Greg’s place. He lived much closer to the theater so it was decided she would meet him there to change and take one car. It was also decided they would eat at a restaurant walking distance to the theater because the valet parking at the restaurant would hold the car for free. Greg sent me many texts teasing me about how he was going on a full date with Lee, and I’d text him back teasing that he needs to treat her right, etc.

I had dinner at the hotel restaurant before returning to my room to work. While I was waiting for my food, I got a text from Lee with the caption “having a wonderful dinner date” and it included a picture of the two of them sitting very close together that must have been taken by their server. Lee was wearing my favorite black dress and showed lots of cleavage. I responded with “your dinner date gets full cleavage, nice for him” and that was followed shortly with “he is buying dinner, he may be expecting something in return ” .

I was in my room working when I got the next text. Lee said the show was awesome and they were going back to the restaurant for a drink and to get the car. Ninety minutes later I got a text saying they got back to his place and she was going to change and head home. She asked if I would still be up when she got home because she wanted to chat. As I was typing my response, I got a picture from Greg of Lee standing there in her dress looking at her phone. I changed my response to “That is a great picture that you let Greg take.” Lee responded, “I didn’t let him, he just took them.” He sent me two more that were similar except in the last one I could see two glasses of wine and Lee was posing. He sent a message with them that said “I told her I sent the picture to you to make you jealous. She laughed and said you should have never let us go on this date.” I didn’t respond right away and I soon I got another picture of Lee facing away from Greg as she looked over her shoulder at the camera.” This was followed by a similar one but she was hiking her skirt and she was laughing. I didn’t know how to respond until I got a message from Lee that said, “What do you think?” I responded, “The one with your dress hiked is very sexy. His idea or yours?” She responded, “His idea. He was pushing for more. Changing in the bathroom now.” I asked “What are you changing into?” and she said “do you want a picture? Ha ha ha”. I waited for a moment then sent back “yes. lots.”

About ten minutes later, I got another picture from Greg and it was Lee standing in the kitchen sipping her wine wearing a blouse and jeans, looking all proper. There were two more candid shots and both of them had Lee looking at the camera talking. I figured it was Greg trying to convince her to let him take more pictures. I was totally distracted by the messages and stopped working. Greg sent a picture of Lee looking at the camera with her blouse un-tucked and a few buttons undone, giving a hint of her black bra. Over the next ten minutes a few select pictures came in with the last one of Lee standing in her jeans facing Greg holding an almost empty wine glass without her blouse. Greg added “OMG she is hot. Never expected this.” I responded with “It is almost like a real date when you buy someone dinner and drinks. Haahaahaa.”

There was nothing for a few minutes and I got a picture of Lee in the kitchen still in her jeans and her bra eating something with a full wine glass next to her on the counter. When nothing came for ten minutes, I figured it was over but then I got a picture of Lee looking at the camera smiling with her hands on her jeans buttons. Three pictures later Lee was without her jeans. The last picture was her facing away from the camera showing her thong that she wore so there would be no lines with her dress. I sent a message to Lee saying “you look great. Your pictures are making me horny.” I didn’t expect her to respond because she didn’t have her phone in the pictures but a few moments later she replied “I made him take his pants off if he wanted me to take my pants off. He is also excited.” I responded with “not surprised. Are you horny?” She didn’t respond right away and said “yes, drunk and horny. He is in the bathroom now. He told me he would sleep on the sofa when he poured us more wine.”

I was about to respond when I got a text from Greg that said, “Don’t worry, your Lee won’t drive home tonight.” I sent back “Good to know. Is she sleeping on the sofa or are you going to share your bed?” A few seconds later he replied, “do you mean give her my bed or sleep with her?” Instantly I sent back, “It’s your place.” I then sent a response to Lee saying “how horny are you? Are you horny enough that you want him to make you orgasm?” There was a delay then I received, “OMG, are you serious? I am drunk and very horny.” I didn’t respond.

About five minutes later I got another picture of Lee standing there in her bra and thong sipping wine. The next one she was facing away from the camera un-clipping her bra followed by a picture of her facing the camera covering her tits with her hands then uncovered. The last one Greg sent was her in a full-frontal nude.

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Nothing happened for a few minutes then my laptop rang. Lee had started Skype video. The image was blurry and moving all over the place at first until it settled on the sofa. Lee put her finger to her lips and then went away. For a long time, nothing happened until Lee sat down on the sofa wearing her blouse. She played with the TV remote. I got a text on my phone from Greg saying “We are done taking pictures. We are going to watch a little TV. I still don’t know what you meant by your last message.” I didn’t respond and three minutes later I watched Greg sit next to Lee with only boxers on. I could hear them talking but the TV was louder. Lee stood up and left and a few moments later she returned with her wine. When she sat down, she was closer to Greg. They chatted for a few moments and then Greg got up and returned with his camera. They took a selfie with their heads together and a few seconds later it popped up on my phone. I didn’t respond and it was obvious they were waiting for the response. When it didn’t come, Lee opened her top a little and they sent another picture. Lee took a sip of her wine and then leaned forward and put it on the table. When she sat back, Greg leaned over and kissed her and put his hand under her blouse. She turned and accepted his attention. He leaned her back a little and started kissing her breasts. It wasn’t long before they were both naked and she laid down on the sofa. I watched as Greg moved between Lee’s legs and could see his dick pointing toward her pussy. He was very, very, large and I could only imagine how hot Lee must be looking down at that huge cock about to enter her. I watched as Lee’s face grimaced momentarily, then turned to a look of lust and desire. He was now on top of her with her legs around him. I watched him slowly pump her as I started to play with my own busting erection. He got deeper and deeper into Lee and I could see Lee’s face as she orgasmed only a few minutes into their love making. It wasn’t long before he came and I came.

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He got up and left and Lee stood in front of her phone, blew me a kiss and turned off the TV then the Skype video. I didn’t hear from them the until the next morning.

I’ll save what Lee told me happened that night that they spent with each other for another story, but suffice to say, when I got back home, Lee and I went crazy on each other recalling this night.

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