[MF] I [36M] got a very conservative [48F] to break put of her shell.

To start, this all happened a few years ago when I was single. Currently I’m in an awesome relationship with a different woman. But I love lurking this sub and figured I’d share my own even if it’s not as good as a lot of stories in here.

To the basics, I am your average white dude, 5’10” 190lbs ish and blue eyes, average dick if that matters.

She is 5’1″ and Puerto Rican, small tits and in pretty good shape for her age. But extremely conservative and inexperienced for her age because of that.

So it all started on POF, which I know is not the best place but I’m from a small town and this was better than tinder at the time for some reason. I was striking out bad with all the women at my age or younger so I started looking higher to see if that helped. So I quickly find her and send a basic hello message, not expecting a reply. But minutes later she responds and we go through the basic chit chat.

Apparently she’s been divorced a few years and has grown kids that are moved away. So I try some low key flirting with her and she is super conservative about it. Tells me she’s not used to talking like that and she isn’t sure she wants to etc.

We continue talking on and off for a few weeks but its going no where. I can tell she has a very old fashioned approach to dating so I make it clear to her that I am not looking for a relationship. So she gets mad but keeps texting me for some reason which gets annoying after a while. So in an attempt to scare her off I tell her I’m moving on unless she wants to get together and fuck.

99% of the time this will make a woman stop talking to you. She didn’t reply for days so when she responded I was shocked. She said she talked to her friend that convinced her to live a little and to sample the goods lol. Anyway I ask her when and she says she just wants to meet and talk first. Like I said she is very conservative… so I agree and we meet up for a late night walk in a park near her house. She fortunately looks like her pictures and I’m surprised by how short she is but in a good way.

So we talk/walk and go through the boring basics again. But I get bored and tell her straight up I want to cum on her face. I’m normally pretty shy myself so this was a gamble on my part, I didn’t think much would come of this so I figured I’d go for broke. She practically stopped in her tracks and looked around nervously, saying ‘right now?’ I tell her, yes. She responds ‘I’m not sure, it’s on my bucket list but I’ve never done it so i don’t know what to do.’

This floors me as I ask some more questions and find out she’s never given a BJ before AT 48 YEARS OLD. I tell her I’m shocked but instead of insulting her or whatever I tell her ill ease her into and and just jackoff on her face. She is surprisingly ok with this so we find a nice dark part of the park with a bench. Fortunately it is near midnight and no one is around. I lay her back on the bench, unzip and bring out my cock and get to it. I try to grab her tits as I do but she fucking bats my hand away.

I’m more amused than angry about that because she’ll let me nut on her face but not touch her tits. She also keeps talking as I’m just stroking it over her face. Fortunately just takes me a few minutes and I pin her head down as I cum a few decent ropes down her face while doing my best to avoid her eyes. She squirms a good bit but smiles and giggles a little, waving her hands around as she isn’t sure what to do. I tell her to just wipe it off with the underside of her hoodie.

Skipping forward now to the good stuff. Months pass and we keep meeting up every couple weeks or so and I push her a little farther each time. Eventually I have her sucking my dick everytime we meet and always facials. It just became our thing and she loved it. She always had some shyness to her but seeing her get more comfortable with it made me even bolder.

I started dirty talking to her which led to me being dominant over her a little more each meeting. I began to talk to her like a fuck doll or something which I had never done but really enjoyed.

In most meet ups I’d text her just before and tell her not to wear panties or a bra. Or id tell her how to do her hair or shave her pussy. Anything I could think of honestly, which was mostly vanilla stuff because I more enjoyed being dominant.

On days she would come over she would walk in the door and before she could even say hello I turn her around, slap her on the ass and feel up her tits as I whisper in her ear things like ‘get the fuck on your knees and suck my cock right now. I’m going to fucking cover your face in cum like the whore you are.’ And she would always do it but always with that shyness.

Over the months I got more and more confident with it and she just sort of became my freeuse whore. None of which I planned, it just happened. Session after session she would come over and I would shove her down on the couch, pull her hair and mouth on to my cock and face fuck her as long or as quick as I could. Sometimes it would just be a minute or less from her walking in the door to me plastering her face in cum. Other times I would tell her not to wipe it off and to suck me until I was hard and ready again. Then I would fuck her and plaster her face a 2nd time. Which wasn’t easy I have to admit, sometimes I wouldn’t have the energy to fuck right after.

This whole thing went on for a year plus until she wanted a committed relationship that I told her from the start was not what I wanted. We still met up several more times and each time she would bring it up and I’d say no. So eventually we just drifted apart.

But I always think back and even look over the old pictures I took of our meetings. I couldn’t count how many times I covered her face in cum as I talked to her like a whore. I haven’t found another woman that enjoyed that kind of thing unfortunately. What made it all so amazing was that I never planned it from the start, I just took one step and another and another unless she said no.

I hope someone enjoys this, I’ve never written about something like this so please forgive any ranting or rambling.

Edit. Word.

Source: reddit.com/r/gonewildstories/comments/jr0gqt/mf_i_36m_got_a_very_conservative_48f_to_break_put