Jess isn't what comes to mind when I think of the MILFs I've seen in porn and she certainly didn't look close to 50. Instead of the busty body with the huge tits, Jess is a tight leggy brunette. She is and has the body of a yoga enthusiast and while she has some fillers that I wish were more natural, there's no doubt she's always been a natural beauty. I met Jess about a year and a half ago through some work meetings, and she stood out right away, partly because the people who had worked with her previously told me how attractive and how intelligent/driven she was. That was evident within 2 minutes of sitting across the boardroom from her and later walking on stage to give an impressive presentation to the entire conference. She was sexy, elegant, and intimidating.

We met in a more social aspect the next night at the conference's social hour and our business conversation eventually led to personal discussions. She was twice divorced, had a daughter that I was closer to in age than I was to her, and how we loved to travel and stay at some of the same places. I asked if I could buy her a drink as the conference social event winded down. She had a dinner but asked for my number and said she would text me for a night cap if I was still up.

I was laying in bed in just my briefs, watching some mindless movie when my phone buzz with a message from Jess. It was 1:30a and she apologized for it being so late, but didn't want me to think she blew me off. She asked if my offer for a drink earlier was a business or social invitation and I told her social. It was a little easier to answer that way considering she was texting me so late and she was a bit flirty in her message. She said while the hotel bar was closed that the bar in her room was still open.

I put on everything but my suit coat and tie from earlier and headed up to her room. We fucked for the first time that night, and while I'm happy to go into more detail on that another time if people are interested, this was just more for background. The next morning we both got up early for the last day of the conference. I told her I'd love to see her again, but she was based out of LA and me New York so that might be difficult. We got out our work calendars and realized we would be both in Chicago in three weeks and made plans to see each other again. This was the nature of our relationship the last 18 months or so. We try to align work travels or make an effort to fly cross country to see each other for a night or two once a month. I've alluded to pursuing something more stable, but she has strictly refused. We're both single driven people, and she refers to me as her "lover" not a boyfriend or partner. We're not exclusive.

A month ago was her 50th birthday and she invited me out for the party she was throwing for herself. It was extravagant. It was at her LA house with a catered menu, servers, enough alcohol to get everyone rip roaring drunk and Jess was done up to perfection. This woman always looked like she could walk the runway no matter the occasion, but tonight she was really feeling herself. She had a sexy but elegant pink dress on to start and then midway through changed into a gold glittery tiny number that no 50 year old should be able to pull off, but Jess isn't most woman.

While I was excited to be there, I did feel out of place. I knew Jess and only Jess since most of our meetings consisted of just the two of us hanging in hotels together. It was interesting to see her away from the office with more of her LA scenic friends. It was fun but I felt a bit out of place and then I saw Jess straddling another man as he was kissing her neck. She was obviously enjoying it, there was no sugarcoating it. I was crushed, I know we were both sleeping with other people , but I had flown cross country to be with her for this night and had barely gotten to speak to her when I had every expectation that I was going to be spending most of the night in bed with her.

I kept my cool, that's all I could do, and I finished my drink. Jess was eventually off his lap (I don't know if they did anything more, I couldn't watch) mingling again and so when I saw a gap in the people coming up to talk to her, I took the opportunity to call it a night. I grabbed her by the hip from behind turned her around and told her I was going to go. "Baby, where have you been?" She hugged me and gave me a soft but short kiss on the lips. "You're busy and distracted, we can chat tomorrow." I removed my hand from her waist and she grabbed it before I could pull away too much. "Wait are you not having fun? Don't leave, I want you here." The guy she was straddling earlier came over and told her there was someone he wanted her to meet and my facial reaction had given it away that I knew something was going on between the two of them. She told him not now and gripped my hand even harder, before telling me "come here."

Jess lead me down the hallway to one of the rooms that the servers had been using as storage for the party. She closed the door and locked it and she made this sexy yet pouty face as she came up to me, "I'm sorry baby... don't leave. I want you here more than anyone." I told her it didn't feel that way, and then she started to kiss my neck slowly while unbuttoning my shirt even slower. "I'm sorry Brian... I just had guests and I didn't want to be rude, because I knew I was going to be with you later." A few more kisses on my neck and now only one hand was unbuttoning my shirt as her other hand slid down and reached for my cock through my slacks. I let her keep apologizing as I kept getting harder and harder. "But I don't want to wait for later Brian.... I want my present now." Her kisses from my neck went higher than she nibbled on my chin, followed by me giving in and kissing her angrily and aggressively.

Suddenly with a party full of people going on right outside the door she was stripping my shirt off and undoing my built. She broke our kiss to move her lips to my chest, while at the same time reaching down with her arm to step out of the thong she was wearing beneath this short gold dress. I pulled her hair and buried my face in her chest, unsuccessfully trying to lower a strap from her dress, but bitting her nipple through the dress anyway. The next few moments happened, quickly but my dick was out with the back of my slacks still hanging above my ass. She jumped into my arms and I pinned her against the wall and went inside her for the first time. I paused at my first thrust surprised how quickly I had found myself inside her tight pussy and longing to hear more of her initial gasp as she felt my weight inside her. This was the only slow thrust I would take while in this room.

Jess kept ordering me faster and deeper with just a soft moan of "Yes" and "Yes" over and over again. Her legs gripped my lower half like a death grip and her heels were digging into my skin. I couldn't get as deep as I wanted while also having to focus on holding her up so I moved her from the wall and carried her over to a couch without my big dick ever leaving her tight pussy. Her dress was now nearly above her stomach as her nice ass hung off the side of the couch. My knees were on the floor and her legs still wrapped around me as I thrusted upwards, using one of my strong hands to grip and hold up that perfect ass. Her nails tore into my back and she bit my bottom lip and pulled it as I grunted with desire. She knew I was close and her tongue moved to my ear which she swirled in my earlobe before saying, "Give it to me baby." As she bit my earlobe, I exploded inside her.

I was still breathing heavy when she kissed me and told me, I had nothing to worry about, but that she "should have made you jealous earlier." We both laughed and more lovingly kissed as we stood up to get ourselves together. We dressed while people called for Jess because the birthday cake was ready, "let them wait" she said as I buttoned up my shirt and she looked in the mirror trying to make herself more presentable after being roughly fucked in a glorified storage closet. When I went to hand her back her thong she told me, "You hold onto it the rest of the night, I want you to know the rest of the party, I only want you." I kissed her, stuck them in my pocket and we both walked out of the room to some subtle smiles and looks. Plenty of people had heard or could infer what just happened.

Jess eventually got her cake and held me hand as her guests sung to her, including that guy she had been straddling earlier. She thanked everyone for coming and for the gifts she clearly didn't ask for but appreciated and then to the entire room mentioned, "Brian gave me my first big gift in the closet just a few minutes ago!" a roar of laughter and hollering came from the crowd and Jess took a bite of her cake and without swallowing pulled me in for a kiss/shared bite of her cake.

Jess broke away from me a few more times the rest of the night but I was a lot less insecure those times. I also had her thong in my pocket and she was sure to throw me some sexy glances the rest of the night. Eventually the night did die down, the guests left and it ended with us in bed together, but not before she changed into some birthday outfit that was just for me, but that's probably for another time too if there's interest.