I was 23 at the time of this story and had recently broken up with my long time girlfriend. She and I had been together for several years and now that I was single I was going on one of the wildest sex binges imaginable. I was insatiable and using every avenue I was aware of to hook up with anyone willing. I was going out to bars and clubs multiple times a week, I made accounts on every dating app I knew of and reaching out to every girl I could. I was playing the numbers game and assuming that even if I was rejected 90% of the time I could at least get a few girls under my belt, and thus far it was working. One night I was checking my messages on one of the apps and saw I got a response from a woman I had reached out to a few days prior.

Anne was 52 and politely told me she was flattered I reached out, but being that I was only a few years older than her daughter and I was just far too young for her. I had a particular interest in the experience of sleeping with an older woman, so I wasn't deterred by Anne's response. I replied back and tried to keep things polite and casual with the sole goal of keeping the line of communication open for as long as I could. She humored me and we chatted back and forth periodically. I won't bore you with the details of each conversation, but I eventually wore her down and we were having more and more blatantly flirtatious conversations. Anne explained that she had divorced a few years ago after discovering that her husband of 20 years was cheating on her with a much younger woman. She confessed she had been hesitant to start dating again and that she had yet to have a successful date since her divorce. Our conversations continued to ramp up and got to the point of us exchanging nudes.

Anne was in no way a supermodel, but she was definitely a cute MILF next door. She was really short, barely over 5', very petite but had big tits for her frame and a small ass. She had dark brown hair past her shoulders with some grays strewn throughout that surprisingly turned me on quite a bit. She wore black cat eye glasses and serious teacher/librarian vibes about her. After several weeks of us talking I had finally convinced her to meet in person. I showed up at the bar she chose and met her out in the parking lot when she called me. I saw her walking towards me with a long black sweater dress and knee high black boots. As soon as she approached me she gave me a hug and a kiss on the cheek and then made a comment about being nervous to go inside because she was embarrassed to be seen with me because of our age difference. She wasn't wrong. There was a blatantly obvious 15 year age gap between us, but we both decided to go in anyway. She ordered a glass of wine and I got a beer. We chatted casually and sipped our drinks for a few minutes when I took my shot and said we should just skip this part and go back to her place or mine. She blushed and said we should at least kiss first to see if there were any sparks. We kissed briefly in the middle of this packed bar before she pulled away, blushed, and said "Let's get out of here." She took me by the hand and led me through the crowd. I couldn't help but notice several people giving us judging glances on our way out.

I got in my car and followed Anne in hers. A short 5 minute drive and we pulled into a development of nice, middle-class suburban townhouses. Not trying to be rude, but it's the exact stereotype of where I would expect a 50 year old divorcee to live. We get inside and Anne quickly pours two glasses of white wine and we head to the couch. We sipped our drinks in silence and I could tell Anne was nervous. Her face was bright red when she saw me looking her up and down. I finished my drink and put my wine glass on the coffee table. Anne nervously sipped hers while I placed a hand on her thigh. I didn't lean in for a kiss or slide any closer to her, I just moved my hand further up her leg waiting for her to tell me to stop, but she never did. She chugged what was left of her wine and put the glass on the side table before taking a deep shaky breath and looking at me nervously. I held her gaze and slipped my hand up until I met her panties. She gasped loudly at my touch. The front of her panties were already soaked and I could tell she wasn't lying when she said she hadn't been touched by a guy in a very long time. I pulled her panties to the side and slipped my middle finger inside her. Her whole body shook and I felt her pussy tighten up almost immediately. I fingered her slowly for a few minutes while she writhed underneath me before she finally pulled my hand away.

She dropped to her knees in front of me on the couch and gave me the look to undo my pants. I swiftly removed my shirt and pulled my pants off so that I was completely naked on the couch with Anne, still fully dressed, between my legs. My dick was insanely hard already, and seeing Anne's tiny hand grasp it tentatively made me almost want to cum immediately. I'm slightly above average, but her little hand made my cock look massive by comparison. She stroked and licked me until I was sufficiently wet, and then took me into her mouth. Her oral skills were just ok, but she really seemed to enjoy sucking my cock which made it quite a bit better. She surprised me by having me lift my legs so she could lick my ass then slipped a finger inside my while she kept blowing me. That was a first for me. Just when I felt myself starting to approach the point of no return, Anne stopped and stood to lift her sweater-dress over her head and then removed her bra.

Finally I got to see her body fully nude for the first time and I was not disappointed. Again, she was really petite but had the signs of an older woman who had children. She had some faint stretch marks on her thighs and stomach and her tits sagged a bit, but her body was smoking hot in my eyes. I stood so that I towered over her and gripped her ass firmly with both hands and then lifted her up. She squealed excitedly and started to kiss me again while I carried her into her bedroom. I playfully tossed her onto the bed and then pulled her down to the edge by her legs. I touched her pussy again briefly and then rubbed her juices onto my cock to wet the head a bit. Then I slowly pressed forward and entered her ever so slightly. She gasped and I watched her hands grip the sheets. I waited for her to relax, then placed one hand on her shoulder to gently keep her in place as I pressed in further and further until I was balls deep. I felt her pussy flex on my cock a few times as she breathed heavily with her eyes closed tight.

"Are you alright?" I asked

"Mmmm, yes. I'm great." she said with her eyes still closed

I took her word for it and started to fuck her with long, slow, but deliberate strokes. She shook with every thrust and soon wrapped her legs around me to pull me in deeper. I rubber her clit with my other hand while I fucked her and it seemed like it had only been a minute or two before she was telling me she was going to cum. I held my pace and once she groaned that she was cumming I couldn't believe how much she was creaming on my cock. The sight alone was enough to push me over the edge and I soon had to pull out and shot my load all over her stomach and flopped on the bed next to her. We lay next to each other laughing for a minute before she got up to clean herself. She rejoined me and we fucked one more time that night before I went home and went on my way. We had a couple more hook ups but it wasn't a very long lived fling.