Cougar from my gym follow up story with role play fantasy [MF]

Hi, all. This story is a follow up from a post I made a couple days ago. See my post history to find it. For those who didn’t, or don’t want to read it, I met a cougar over a couple weeks ago in my gym in SoCal and eventually summoned the balls to talk to her and asked her out. She invited me around for a drink rather than go out for one. I had the best night of sex with her but if you want to know more, check the post.

I had no idea that people would enjoy the story as much as they did as I had a lot of people message me directly about it. We had met a week after our first encounter and this one is possibly even better than the first one, though our first night will always be my favourite personally.

So many have wanted to know more about her so I’ll explain a little more. I won’t post pictures of her because I respect her to much to do that but I can explain more as she is anonymous. She is early 40s and was married for a fairly long time but it didn’t work as it ended up being a dead bedroom. Said it took a long time to start to love herself after the marriage breakdown after losing confidence. That’s why she looks so good as she has worked hard on her body. She is a little above average in height for a woman, not tall though. Very nicely defined legs, butt, arms and has a big chest. What I ove most though is her face. She has such a soft feminine look and a smile that could brighten the darkest day. Sure I love a hot body but the face is really the most beautiful part of a woman to me.

She had remained single for a long time and said she had so much pent up sexual frustration to release and that she is glad she found a hot young guy to unleash it on. Her words haha. It’s such a great feeling being able to make a woman feel special like that. Not going to lie, it’s a great ego boost especially after being cheated on personally. Life has a funny way of bringing two people together at times.

Anyway, back to the story. Straight after our first meeting I couldn’t stop thinking of the night and how amazing it was. I couldn’t get her out of my mind. She consumed my every waking thought. I didn’t want to seem too clingy as I just wanted to impress her. My fears were put to rest when she was the first to reach out. She sent me a message saying that it was the most incredible night she had experienced in her life. Said that I had awoken a side to her she thought was dead. That was so great to hear. She also said my ex girlfriend was the stupidest woman alive to dump me with how well I kiss and eat pussy. Now THAT may be the best thing anyone has ever told me. I was trying to control my ego but after that I think it was developing it’s own beating heart haha. She said about doing it again and of course, I was interested.

We made plans to meet a few days later and I wanted to be at my best so I decided to not cum until I was with her. I also started zinc supp as this always makes me hornier and I’m able to cum more. I wanted to give her my absolute best! She had messaged me before our planned meet up night asking if I could push it forward as she was home alone and horny thinking about me. As much as I wanted to drive to her so fast that passing motorists thought I was filming the new fast & furious movie, I couldn’t. It was my birthday and my friends had plans. I told her this and she made a big deal about why I didn’t tell her it was my birthday. Now, I hate my birthday. It’s just another day to me and I hate people making a fuss. She wanted to make it about me even though we had really, only just got to know each other. She then talked me into the best possible birthday gift I could have. A role play fantasy..

She said how she loves to dress up and go the whole nine yards. How she loves to role play and her ex husband always thought it was stupid. I have always wanted to try it but never found anyone and since she really wanted to, I was more than happy to give it a go. She said my present was choosing what she would dress as. What the scenario would be. I said I’d think it over and get back to her by the end of the night. Every guy I knew had thought about what they might want to see a hot babe dressed as and I was no different. Should I go cop, office worker, stewardess or something else? Now, I was having a few birthday beers with my boys and that certainly aided in finally deciding in my drunken state, Teacher. A sexy teacher and her naughty student role play.

She thought I might choose that and said she would find the perfect outfit for me. I’m sure she would. As the day arrived I was so horny thinking about her and the night ahead. I wanted to look my best and that means a gym session. I wanted to get a good pump in and have my muscles at their biggest for her. Who do I run in to at the gym? Yep. Unreal. Couldn’t make this stuff up. I hadn’t seen her since that night so it caught me off guard and my heart was pounding. I didn’t know whether to kiss her or just hug her. I decided to give her a kiss on the cheek and hug since we were in public. The sexual tension was palpable and you could have cut it with a knife. Was a little weird though as I wasn’t expecting her to be there since I had gone at an earlier time to normal. As I had finished well before her I went over to her and gave her a hug goodbye. I whispered in her ear “I hope you’re ready for me, insert name”. She replied “it’s MISS insert name, to you”. That sent a tingle down my body. Sounded so hot. As we finished the hug I gave her a little slap on her ass which she wasn’t expecting but she definitely enjoyed it as I seen her bite her lip and look my way as I left.

I went home and shaved the merchandise to look my absolute best. I’m sure she would have done the same as she had the most smoothest pubic area. So hot! I chilled at home before getting ready later and out some nice clothes on with my cologne and went to hers. I would be lying if I said I wasn’t nervous again. Especially knowing what she would be wearing. Now, we had talked about how it would play out. We both agreed to commit to our roles to try get the best out of it. We had some ground rules that we both knew before I even entered her place. The first of which was I had to call her ‘Miss insert’ name and she had to refer to me as ‘Mr insert name’. The second was, anything she said goes. Meaning I had to do whatever she told me to as she was my teacher. That was fine with me but your mind does wander thinking “oh fuck, what if she makes me do something really crazy” haha. The third and final rule was we could not break character until the end unless someone said the safe phrase which was ‘Cougar’. Oh and since our first meeting I wore a condom, she said that if I wanted to I could not wear one since I had told her that I was clean, which I was and she said like wise. I normally still like to wear a condom especially first time with a girl because it makes me last a bit longer. It’s always that awkward convo but we cleared some things up and were both on the same page which was good.

As I knocked on her door, my heart was racing. In a good way though. The best way it could. She answered after what felt like an eternity and greeted me in the hottest outfit I had seen. Seriously, she looked amazing. Heels on that showed her amazingly defined legs, a tight short skirt that highlighted my favorite man made world wonder – her ass, and white button up shirt with some top buttons undone revealing her amazing breasts. She could be on internet ads, ‘this one trick destroys erectile dysfunction’. My jeans got tighter instantly. To top it off, she had her hair in a mysterious bun with a nice shade of lipstick on to highlight her incredible lips. I almost broke character instantly but quickly stopped myself mid speech and she just said, “you’re late, Mr insert name”. “Sorry, Miss insert name” I replied as I entered her ‘class room’ for what would be the best time I have ever experienced in a ‘class room’..

I was worried I would ruin it by laughing but since I hadn’t known her for that long it was actually easier than I thought to just go with it. She told me to sit down in her home office room which was a nice touch. I had no idea if she what she was going to do or say, I was just hoping it wasn’t a surprise quiz as I hadn’t studied for any. She told me I impressed her in our first meeting but said she wasn’t sure if I could reach that level again. I knew she was being cheeky so I smiled and said depends if you are in your best behaviour. She surprised me by keeping in her role and said no talking back and for that I had to take my shirt off. I obliged. She also said because I was late I had to remove everything bar my underwear. This was quite unusual protocol for a school, I might have to have a word with the principal. It was actually pretty hot undressing while she stayed dressed. She said to follow her and I did, we walked to her bedroom. I had to sit on the ground which was strange. I was finding it a little strange as I had never done anything like this but I said I’d go along with it. She sat cross legged on her big bed facing me. What now, Miss insert name I asked, being a smart arse. She told me, I was not aloud to take my underwear off until she was sexually satisfied and I couldn’t take her clothes off. I was confused. How could I make her cum without taking her clothes off? She also mentioned that I could not stand up at all either. I was confused and asked her what I was thinking for her to say “Me insert name, I have made it easy for you”. She then in crosses her legs and I see that she is not wearing any underwear. Oh, my God..

I’m not sure what it is but I find it sexier when a girl is wearing clothes or lingerie rather than being completely naked. Especially when they aren’t wearing underwear. I was hard as a rock and she could see it too but didn’t even acknowledge it. I couldn’t stand so I walked over on my knees and kissed lower leg and worked my way up while she sat on the bed. I took my time on her thighs as I wanted to make her as wet as possible and begging for it. She had a short skirt on so it made it easier to work my way to her amazing pussy. Just the smell was amazing. Was making my mouth water, literally. She did have to pull it up when she seen I couldn’t quite get to the sacred area. As I had took my time and she was definitely wanting it, I slowly and lightly licked the whole of her pussy and she moaned so sexily. She was dripping wet and tasted amazing. Don’t know why guys say they hate eating pussy. I would choose that over getting my dick sucked everyday of the week but I love to please a hot woman. I kissed her inner thigh and kept away from her clit to tease her. I also used my fingers to softly pull apart her lips and held it then id let go and go back to kissing right near her lips which had her quivering with anticipation. I then have her another full lick over her pussy and then sucked on her clit lightly which she was dying for. I thought I had her as wet and turned on as possible so I then went to work, first starting slowly eating her. I then opened her lips again and exposed her beautiful clit. I reckon if I seen more of my teachers clits in high school my grades would have been far better than they were. As I sucked on her clit I then slipped one finger in ever so slowly, pulling it out then sliding it in a little further each time to her delight. She began to moan louder and louder which made so turned on. I was trying. To control myself as if she took my underwear off now, it would be like the scene from The Shining where the blood comes out the elevator except it would be my pre cum instead.

I had her right where I wanted her, taking my time with foreplay had built the sexual tension up and that is key in order to make her and women cum. That’s what has worked so well for me. As I put another finger in after driving her wild with just one, she moaned even louder and I could feel her ready to explode but she wasn’t going to cum until I was ready. The come here motion technique worked wonders as it always does and as I felt her orgasm building I out my other hand above her pubic bone which opens up the g spot which had her nails digging into the back of my neck as she pulled me in as close as humanly possible. I had my mouth on her pussy and just as I could feel her about to cum, she stood up and told me to lay down. I did and she pulled up her skirt then sat down on my face with her knees and legs across my chest with her arms out stretched in sort of a yoga pose. Not sure of the name but that simple one that everyone does. Her pussy was sat on my face and I then ate like I have never ate before. She was sort of grinding too and started to scream “fuck, fuck, fuck”. She was about to cum and even though it was hurting my face, I wanted to make her cum on me. She moaned as loud as I have ever heard and her body went into a full convulsion as she came all over my face. Fuck, it was so hot. I seriously thought I had came too. Wouldn’t be the first time I have came eating pussy and probably not the last.

She laid on top of me as we both were exhausted, especially me haha. She said “good boy, Mr insert name” and pulled her skirt back up. She said I had now been rewarded with whatever I wanted to do to her. That was the best thing to her. I asked “Miss insert name, can you take your top off?”. She started to un button as I kissed her stomach and worked my way up. Her boobs were amazing and I love kissing them. I licked her nipples as they went hard and she moaned some more. I sucked them and grabbed them and then told her to bend down in doggy position. She did and had her ass in the air. Fuck, it looked so good. I kissed her neck and slapped her ass which she moaned to. As I worked my way down I kissed her sexy butt and squeezed it. Again, I licked her pussy which had her saying “fuck”. I wasn’t sure if she could go again but that wasn’t my aim anyway. We hadn’t discussed this specific thing but I thought I’d go with it and if she didn’t want to do it she would let me know which I would be fine with. I began to softly lick and kiss her ass cheeks and I’m sure she knew what was about to happen..

My heart was racing as I then licked her butt hole. She let out a massive moan and said “oh my God Mr insert name, yes”. I guess that meant she was ok with it haha. Eating ass us the absolute best. Especially combined with pussy play. I ate her ass like a man possessed. She was LOVING it. I then slipped a finger into her pussy and did the come her motion but this time from the opposite angle. I have found that this works just as well, if not better. Wasn’t long before she went wild and was cumming again. Gushing. Was so hot. I kept eating her ass before I slowly pushed a finger in and that had her going crazy. She had her face on the ground and her ass firmly in the air, wanting it. I had done ass stuff before so I knew to build it up and make her relaxed for her pleasure. When the time was right and her ass was so wet I then used a combination of her juices and then my own to lune up my dick. I was covered in pre cum and was ready to explode. She knew what was coming as she moaned and said “I want you inside”. Hearing that had me on the verge of blowing my load haha.

“Sorry if I cum quickly, Miss insert name”. “I want you to cum, now” she replied. The best thing to hear as I was dying to. I slowly went in with the tip as she moaned and moaned. I pulled out then went back in slowly but a little further in, then again and again. Now, I’m not a small guy at all, well above average and she had commented on that but by taking my time, using fingers first, plenty of natural lube and going slowly, she was enjoying it. She did make a couple initial groans but as she relaxed and I went in, she moaned with pleasure. I could lie and say I then pounded her for 10 minutes until she came 3 times in a row. But no. I fucked her slowly and picked up the pace as she was moaning and saying “fuck” over and over until I felt it coming and fellas as you know, when you go past that point of return, there is nothing stopping it. Bunker down, lock the hatches and prepare for landfall. I told her I was about to cum and she moaned “cum for me, Mr insert name”. Hearing that sent me over and I came as hard as I have in my life. I thought of pulling out but then she said I could do whatever I wanted. She did not mind at all though. She collapsed as did I and I laid inside her still catching my breathe. I can’t believe how good this has been..

I pulled out and I felt bad as I had filled her up. I went and got a towel and cleaned her up then we both showered together and washed each other. I felt as if I were in a dream, a wet dream. My wet dream. After suffering a shit break up with a shit girl, it’s amazing what life can throw your way. We spent the night together and still remain in touch.

That was a lot longer than I thought it would be but it felt good to get out. I’m not sure if people will like this as much as the other one but I hope some will. I’ll fix the grammar later as I’m sure I would have made a few mistakes since it took so long to type this out haha.

Source: reddit.com/r/gonewildstories/comments/ejsat0/cougar_from_my_gym_follow_up_story_with_role_play