“shhhhh” May giggled as she led her son towards the private seating area. “Remember it’s May in public honey” she winked as she patted the seat next to her beckoning Jake to sit next to her.
She smiled at as he put his arm around her. Blushing as his he pulled her close and kisses her lips softly. He was tender and not forceful. He knew to hold back at this moment just to feel the connection between them. As the finished she looked at him and thought back on what brought them here.
It had started out innocently enough about 6 months ago when they bother swiped right on one another. It of course was a joke on both their parts. They laughed about it when they both saw the other had connected with them.
They were both single and both on the prowl so to speak. She had teased him about his age limit being set as high as it was but of course he pointed out how low hers was and she sort of laughed it off.
Over time they got to messaging each other back and forth not as mother and son but as old friends. They would inquire how the dating life was treating each other and share stories of funny or embarrassing events that transpired in their dating life. It wasn’t sexual by any means and May loved that her son was being as open as he was with her. In person it was back to mother and son relationship but online behind a screen it was a safe zone of sharing.
Things changed about a month ago though. It was late at night and Jake saw his mom was still up and messaged her and asked how her date went.
M-It was fine. He took me to all the right places and said all the right things and if he had gotten food poisoning I might have woken up somewhere else tomorrow. Lol
J-uhh I didn’t need to hear that!!! (Jake laughed to himself)
M-Well you did ask. Besides I know there have been many times you’ve shown up back at work wearing the same thing as the night before. I hear things.
J-lol ok ok guilty as charged. I don’t know what I was thinking you’re a grown woman.
M-thank you. What about you? How was your date?
J- Wasn’t to bad. I’m not saying she’s the one but I’d probably ask her out again.
M- so what base did you get too :P
J- LOL I’m not telling you that. How would you like if I asked you that.
M- We were getting to second base when he fell ill. So there ;)
J- lol ..ok ok you win. Monica and I were at second as well when she told me that as far as we go.
M- But of course you wanted more. I’m think it’s awesome you respected her wishes.
J- Well I had a great mom who taught me about respect.
M- maybe you should tell her that some time. :P
J- Well I wouldn’t want it to go to her head. Although from what I hear she doesn’t mind rounding to second base on her dates and from the sounds of it would have rounded to home had there not been a cancellation of the game. Lol
M- lol… remember respect the woman’s wishes!!
J- You know it’s been nice talking like this. I feel like we get to know each other a little better. I feel like here I can be open with you more.
M- same here. I guess I wouldn’t have normally have told you what base I get to. But like you said here it feels a little different like I’m talking to a good friend I can share ideas and feelings with without judgements.
J- Like how you can already get to second base after one date!! Lol….Im kidding.
M- Hey when a woman knows a woman knows.
J- How did you know with him?
M- How did I know I was going round to third with him?
J- Yeah
M- From our conversations before the date. How he acted during…and the fact he hadn’t sent me a sick pic in the first 3 sentences after saying hi.
J- So you are saying don’t send the dick pic so soon. Got it! So send it like what 2 hours after saying hi :P
M- lol…I’m pretty sure your mother taught you better than that. It’s always polite to wait for someone to ask for one. Hehehe.
J- Yeah my mom did teach me well.
M- So as your friend asking…have you ever sent one?
J- maybe 1 or 2 times. I mean it was back and forth…never with my face attached to it though.
M- well of course not. I mean if you could get down there why would ever leave the house :P
J- ha! So as your friend have you ever sent any naughty pics out.
M- Hmmm maybe 1 or 2. Again no face attached…
J- So scandalous. You’re old enough to be someone’s mother!
M- I am but everyone has their wild side don’t you think?
J- I agree. We are all human after all.
M- exactly
J- So I’m getting to know all sorts of things about you tonight.
M- Well I’m open to all questions you may have. I mean friends don’t keep secrets do they?
J- good friends don’t.
M- how about something simple as we get to know each other.
J- Shoot
M- what’s your type of woman?
J- really I don’t have a preference of short or tall…just someone that takes care of themselves. You know wakes up makes somewhat of an effort. And of course has an ass that won’t quit!!
M- lol…so an ass man
J- what about you
M- about the same. He has to be gentle though. I like a caring soul. With strong arms to pull me close.
J- take charge kind of guy?
M- you could say that.
J- What kind of dress did you wear on your date tonight?
M- it was a black flowing dress. Straps around the neck…showed just the right amount of cleavage. And you?
J- Well it was a dress but blue jeans and a button down. No under shirt…short sleeve.
M- Boxers or Briefs?
J- boxer briefs :D
M- lol
J- And you?
M- umm…..thong…lol …wait would a friend tell another friend this?
J – yes…yes a good friend would. Lol…lace or….
M- yes lace…black…..thigh highs
J- so is this a standard outfit for you?
M- special occasions…what’s your favorite place to be kissed?
J- my chest…and you?
M- my neck… Just around the collar bone.
J- and favorite place to be touched….
M- my lower back…my thighs….and you
J– my neck….my chest….my legs. What about kisses on your inner thighs?
M- well who wouldn’t…..
Their conversation went on like this for another hour. May told her son where she liked to be nibbled. That she once was tied to a bed and spanked and that she was multiorgasmic among other things. She learned he loved to lick a woman to climax, take a woman from behind and take charge when the situation called for it.
Maybe it was the fact they were both denied release that night that got them talking. Maybe it was just nice to share with someone who wouldn’t judge or share with someone there was no possible way of getting with. Either way neither of them slept well that night until they both brought themselves to release on their own. Each, as she would later learn, reading their chat and thinking of one another.
There would of course be another couple chats before tonight. Each more risque than before. But things had changed from that night. When she saw him next as mother and son the time she knew things had changed between them when she found herself standing before him in her outfit she picks for special occasions.
To be continued
Source: reddit.com/r/eroticliterature/comments/cmyx3q/the_first_date_part_2