Part 1: [https://www.reddit.com/r/Erotica/comments/d47yif/my_first_time_helping_an_adult_virgin_encounters/](https://www.reddit.com/r/Erotica/comments/d47yif/my_first_time_helping_an_adult_virgin_encounters/)
Hi S,
Wow, last night was crazy. I cant actually believe I did that. I have fantasized about an interactive sexual encounter like that for so long, as I write that out, it looks just so pitiful, anyways, last night was amazing. I have never let anyone see me like that, it felt very thrilling, and it was a huge turn on,but honestly today, the whole experience has left me feeling very vulnerable and exposed.
I have never understood how to interact with people very well, so last night was way way outside my comfort zone. You were very kind, and I think you are very sexy – but I don’t think we should chat anymore. Like I said before, I think you have been so so sweet, but I know I am not really very attractive, and I am pretty sure you can do better than a middle aged virgin that could stand to drop 30lbs. I am pretty sure if we keep going, I will disappoint you eventually, so I want to stop here, before I do. Thank you, Im sorry. -Z
Z,
I got your email, wanted to let you know I had fun last night as well. I think you are crazy sexy, and being there as you try things for the first time was thrilling to me. I was disappointed to learn you didn’t want to be in touch anymore, and as I have said the whole time, I will always respect a no. If I don’t hear back from this email, I wont write you again.
I hope this isn’t out of line, but, you are in your 40s, you have almost no sexual experience,but, you want sexual experience. There is a man that wants to have sexual experiences with you, and you find him attractive, and he has been really nice to you, and preliminary sexy stuff has been really fun, and even after sexy fun, he has continued to show interest- are you sure this isn’t kind of a perfect set up?
What if you just adapt the mindset that I am a practice man. That we are not looking for romance, that we are looking for education. Honestly, watching you try stuff for the first time is a huge huge turn on. I know you don’t know what you are doing, I don’t expect something different. If you want a free pass to ask all the questions, or try out what gets you hot, or explore a mans body, with no judgments, no criticisms and no obligation, I would be happy to be that man. I don’t shock easily.
Regarding your body and your looks. I was raised on Playboy, not internet porn. Back when women had curves and body hair. I am attracted to my peers, (no need to point out I might be a bit older). I have seen you naked, and exposed, and I want to see more.
Also, fyi,I know this is pushing into very sensitive territory (pun intended), but did you know there is an entire fetish community dedicated to women with larger clits? I think your pussy is beautiful and perfect. It would be a privilege to see her again.
Even more importantly, I am an almost 50 year old man, there are no small number of flaws, I am going to need you to overlook on my body. But here is the thing – there is no rule that only young sexy hard bodies can have porn star crazy sex. There is a party going on, and you are invited.
I will be free around 9:30 this evening, if you want to find me on line. Please have the plug in your ass when you do.
-S
The notification popped up at exactly 9:30. “hello S, I just wanted to respond to your email for a second, cant chat long” was her opening. I smiled a big grin, and replied “Shall I call, or are we texting”
“Texting for the moment. It is a little easier for me to say what I want, here first”
“okay, Z, what did you want to say”
I waited, watching the notification “Z is typing” pop up then disappear, then pop up again, over and over for minutes on end. Finally “not sure”
“that was a lot of typing for ‘not sure’” I came back “You know this is your chance, hopefully just your first of as many as you want, to just finally stop being ashamed and say what you actually want. I wont judge, I wont make fun, I will be supportive, no matter what”
“tell me Z, do you have the plug in, as I asked”
“Yes” came back almost immediately “did you make your penis hard yet?” I cant say why exactly, that the awkward sincerity of her inexperienced dirty talk was a turn on, but it was.
“I am not hard yet, we haven’t really gotten started, but I am naked, did you want to turn on cams?”
The invitation came to join her cam, and there waz Z, Eyes bright and wide, cheeks a bit flushed, her robe drawn. She looked fresh from the shower, hair wet and slicked back.
“hello beautiful, so glad to see you again tonight” I said sweetly ”you look cozy” in a transparent attempt to transition subtly into the dirtier stuff….
“I want to see it. I want to see it not hard. “ Z said in an almost flat affect “ I want to see it soft, and then I want you to make it hard, and I want to watch”
I was tempted to step into a dom head space, to remind her ask nicely, to delay her gratification, but on second thought, this seemed like the time to just follow her lead, so I leaned back in my recliner, and adjusted the camera, to show my cock, still resting but starting to wake.
“Wow, that’s what they look like most of the time, huh? It gets kind of small, I didn’t know that”
“Aw shucks, bet you say that to all the boys” I smiled back
her face dropped, “I am so sorry……I”
“Z, my ego is fine, I shouldn’t have joked. The last thing I want to do is discourage you from speaking freely, after I explicitly invited you to, I am having lots of fun, please don’t stop. And yes, it does get a lot smaller when it is soft, do you want to watch me get hard?”
“ok, are you sure, I didn’t mean anything, I am sure it is big enough, I just don’t have anything to compare it to, so I didn’t mean to.. I really like your penis, I mean it doesn’t look too weird or scary or anything”
I had been seduced long enough, “ I want you to help me get hard, would you like to do that Z” I could see her starting to get flustered a bit, regained her confidence “how can I do that?” she asked, coyly, standing up , taking a deep breath,and letting her robe drop. She did a turn and wiggled her pretty round bottom for the camera, showing the stopper keeping her ass plug in place, then sat down, leaned back and put her feet up like the night before, straddling her computer screen.
“Beautiful, Z, you are amazing, look at your sexy bod, damn I wanna touch” came out as I reached down and started squeezing by balls, and grabbing my limp dick, stroking slowly and steadily. “Spread your pussy for me”, she complied easily, and my strokes grew longer as my cock did the same, and as she used her middle finger to push her huge now swollen clit in wide slow circles, I got so hard I almost came after just that minute, but I let go, not soon enough to prevent the first clear drop of pre-cum from dripping out. I rubbed my finger over it, so show her, how hot she was getting me
“is that it? Did you just cum?” She looked both crestfallen and proud, “is it over, did you finish”
It was really hard to remember she had absolutely no experience, “No, nothing really came out, just a drop” “Oh” she came back, “I didn’t know how quickly you made more, I thought maybe it was all used up yesterday, or something…..”
“Don’t laugh don’t laugh don’t laugh don’t laugh” was the only thought I could hear, but pushed through with out even cracking a smile” no no, plenty left”
“Good, I want you to cum for me again. I wish you could cum on me, I want to feel it, I want to rub it on my skin, and my tits, will you cum for me again?”
Z had been working herself into a lather, rubbing her clit in cirlcles, then pushing two fingers inside, and fucking herself for a few seconds, before going back to her clit. “ I liked watching him grow like, I liked you getting hard watching me. My wet wet pussy got you hard” she panted. By now her middle 3 fingers were employed in pushing down on her clit, rubbing up and down, as one might quickly flip a switch.
“I want you to squeeze that plug in your ass as hard as you can, clench your asshole and stop playing with your pussy. I am going to take my time with you” sensing now might be when I take control of the situation.
Z gave me the devilish smile I saw the night before, ignored my words completely, slid deeper in her chair and worked her clit harder and faster. She slid her ass and pussy almost all the way up to the camera, and growled from someplace deep inside “ I am such a beautiful slutty whore, I want your dick “ and increased her pace, now hips bucking in time with her fingers, She moaned, then squeaked and convulsed, pussy twitching as the plug starts to slide out of her ass, she sits upright, almost violently driving it back in, pushing her over the edge. Z shuddered and lay back, continued to twitch for a moment, moaning, primal, ecstatic . Her body relaxed, as the plug slid out to the floor. Z closed her eyes, took a long deep breath, and made a happy sigh of satisfaction, hands folded across her bare middle, deeply tranquil. I watched wondering if she had gone to sleep, then she gasped a huge breath of air, as though she had just surfaced from the water, and like that, she was back.
WOW, That was better than yesterday!, did you cum with me? I wasn’t watching the screen, That was wild! I am swirling”
“no,” I said “ I really didn’t even get started…” I don’t think she heard a word I said
Z was still visibly trembling a bit…”wow, I am exhausted, that was amazing, did I say that was amazing, because it was. WOW”
I replied, “I thought we were just getting started, I am still pretty hard…..”
“That was amazing, I cant believe how you have helped me to open up, I guess I was ready, or something, but wow I am spent, just want to cuddle up and sleep, I feel almost dreamy…”
“Ok sexy dirty girl, get some sleep, find me tomorrow if you like”
“Hey S, I really do like your penis, good night”
Source: reddit.com/r/Erotica/comments/d4kfus/my_first_time_helping_an_adult_virgin_encounters
part 3 -[https://www.reddit.com/r/Erotica/comments/d53lfw/my_first_time_helping_an_adult_virgin_encounters/](https://www.reddit.com/r/Erotica/comments/d53lfw/my_first_time_helping_an_adult_virgin_encounters/)