Similar to my previous story about about hooking up with an old coworker, this one takes place around the same time period, I was in my early 20s at the time and she was in her mid 30s.
This particular woman was hired on to the company I had been at for a few months to help with customer service and shipping, which is what I was doing at the time as well. When she walked in, I knew that I was in some amount of trouble. I really liked shorter women at the time and my best description of her follows; roughly 5ft 2inches of height, brunette, I could tell she had at one point had a child. Just a small stomach pouch, which whatever, but her chest never went down after she had her children. If I remember right, she told me she measured around 38DDD. So I did my best to not let my side glances linger….
I was assigned to train her, so we got to talk quite a bit between calls, emails and shipping orders out. There were constantly other people floating around so we didn’t venture into any nsfw conversations. A few days pass and it’s obvious that we have some good chemistry talking to each other and we trade numbers, which is when we start to get to know each other’s history a little bit better. She moved to the state to be closer to her kids and was new to the area and was single. So we agreed to try and have a date on a weekend she didn’t have custody of her child.
We didn’t send super explicit messages or pics, but things seemed to be going well between us leading up to the date and in my opinion her body was amazing, so she was in my thoughts on lonely nights. Cut to the night, we end up going out for dinner and a movie. The details are a bit foggy on what the movie was, but afterwards we went back to her place. She seemed apprehensive to let me in, turns out she was so new to the area she didn’t even have much furniture. The normal amenities a good apartment would land you, but just a bed and a good laptop for entertainment. I told her it’s alright and she let me in. We sat talking for a while, without much else to talk about we got into detail about our past sexual experiences. Up to this point we’d kissed a few times, but between that, her body and our conversation I was already turned on.
I needed to use the restroom, standing up from the floor it was obvious I was pretty hard. She winked at me and showed me the bathroom. Walking back out, sitting next to her she laid her head in my lap and I let her know she had been in my fantasies lately; her reply was “It doesn’t have to be just a fantasy.” Then she climbed into my lap and we started to make out. Within minutes we had taken each others shirt off and I got her bra unhooked, it clasped in the front and her breasts stayed up without any help from the bra. They felt so nice against my bare skin. I began to explore her body with my hands and mouth, tracing her areolas with my tongue and teasing her nipples. She let out small gasps as I did so, laying her back I kissed my way down her stomach and began to undo her shorts. I could smell her sweet scent before I even got her completely naked.
I pulled her shorts off and traced by lips up one leg and stopped kissing her between the legs on her panties, she was already drenched. I slipped her g string off and had to undo my zipper and unbutton my own shorts to give myself some room to breathe. I spread her legs apart and slid my tongue inside her, starting to tease her clit with a hand while I massaged her tits with my other hand. She kept me down there for a while and I lost track of time until she tapped on my shoulders and moaned for me to fuck her finally. I moved to remove the rest of my clothing and she took my dick in her mouth, “If your dick is wet you’ll slide right in.” And I did. It felt so good, possibly the wettest woman I had been with to that point and she gripped my well. She told he she did kegel exercises daily and it was obviously true.
I played with her breasts, teasing her nipples with my tongue and we kissed passionately until I couldn’t take it anymore. I asked if she had protection, she moaned “Cum inside me” and wrapped her legs around me keeping me where I was. Still mounting her I kissed her as my dick finished pumping and twitching inside her. We stayed like that for a few minutes before she unwrapped her legs. Sitting back up, she mentioned staying still because her legs we to weak to walk, so I began to massage her legs and feet.
I kept touching her body, massage her thighs and lifting her up slightly to massage her ass. I leaned forward and kissed her while she was still elevated. It had been 5 to 10 minutes since we finished and when we kissed my dick rubbed up against her labia and I instantly got hard again. Between how wet she still was and the cum dripping out of her I was able to thrust inside of her again. She tightened so hard around me, her body began to shake and I have her the first full body orgasm she’s had in months. She hadn’t expected the thrust, thinking we were done. I keep pounding in and out of her until I cam a second time. She shook the whole time and was tighter then I had ever experienced before as well. The rug burns were worth it.
Over the course of us dating the next few months, I let her know blowjobs don’t get me off. They can keep me erect but never get the job done. She took it as a challenge and tried several times. The best time she blindfolded me and made me lay with my hands behind my back. She used her mouth as best she could, it was great and then she wrapped those DDD breasts around me and pump up and down on me with those licking and sucking on the top of my manhood. Still I wasn’t close. She cheated in my opinion because with my hands pinned behind me she straddled me and within minutes her pussy was so good I was right there and trying not to cum. She hopped off and resumed titfucking me and sucking on the tip. She got her taste of victory….
Source: reddit.com/r/gonewildstories/comments/wal0oc/mf_my_experience_with_a_cougar_m22f33
33 really doesn’t qualify as a cougar
Hot!