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/)
PART 2-[https://www.reddit.com/r/Erotica/comments/d4kfus/my_first_time_helping_an_adult_virgin_encounters/](https://www.reddit.com/r/Erotica/comments/d4kfus/my_first_time_helping_an_adult_virgin_encounters/)
“You there? hey where did you go? Been looking for you for days?”
Z finally texted back
“Hey S, Im here”
“Everything ok? Thought I would hear from you a few days ago”
“ I am fine, this is just a lot to process. The other day, I feel like I just went crazy or something, I am pretty embarrassed” Z said “I am a very in control person, I like to know what is going to happen next, and with you I don’t feel like I know what is coming next”
“hmmm, well if it helps, I really enjoyed crazy and out of control, and, if we can be very honest, you “lost control” in very controlled circumstances, and by choice. And, you enjoyed it, no?”
the messenger face chat rang, and I picked up.
I didn’t know Z well enough to read this expression, She looked better composed and more smartly dressed than I had seen her before. She looked like a powerful woman, a professional or something, wearing one of those aggressive business skirts that looked expensive. It occurred to me, I had no idea what Z did,
“wow, you look sharp, is this what you wear around the house?”
Her tone and body language softened and she said she had just gotten back from work. “this is my ‘Bitch Getting Shit Done’ outfit” “I bet it is” I came back “what do you do? If you don’t mind my being nosy.”
“I don’t, I work in forensic accounting for a law firm” she started “You see, what that is…..” “I know what it is, well actually I don’t, but I have the answer I wanted, but we aren’t really here to talk about work”
“no, I guess we aren’t” Z sighed “ To be blunt, like you, I am worried you are screwing with me, if I can be honest.” “what? Why?” “I have never had any kind of rapport with men. Everything has always been awkward and halting, it never goes right, and I end up alone and frustrated. That is the way life works for me. This, this, well what ever we are doing is going too smoothly. I am not that hot, no one has ever looked at me like you do, I feel like I am being set up. Am I being set up, S?” Z looked so serious, my idiot’s grin confused her. “Why are you smiling, are you fucking with me?”
“No, no, no, no,” I laughed “ I am smiling because you think that this has been going smoothly. In the world of anonymous internet hook ups, this has been a lot of work., that sexy business suit does it for me by the way…”
Z got serious again “ I am not stupid, you know. It makes me uncomfortable when you say things like that, I know you are trying to be nice, or whatever, but I can see what I look like, I have a mirror. It makes me question how much to trust you. You don’t need to flatter me to get what you want…”
“has anyone else ever seen you naked?”
“you know the answer is no, I have told you that already”
“if I asked you to do something well beyond your comfort zone, something completely perverted –anonymous, completely anonymous, no one will ever know it is you, but completely perverted, that will prove to you, beyond any doubt, that you have a crazy sexy bod, would you consider it?”
“that was not the response I was expecting, and you have caught me off guard, and curious. What pervy scheme do you have, to prove that I am a sex goddess and not a frumpy middle aged virgin? If you truly believe you can prove I am a sex goddess, I would be a fool to say no, at this point, right”
Sex Goddess, that will work perfectly. Here is what I want you to do, I want you to get off the computer with me in a moment, you will then, go to your desk, and in clear letters, make a sign that says “WORSHIP ME”. After that is complete, I want you to strip down, naked, heels up, straddling the computer, as I have seen you do before, then, sign by your side, call me back from your phone, not your desk top”
“WORSHIP ME? Isn’t that a little…..” “You said Sex Goddess, now can you do as I ask?”
“I will call back in just a few”
Z seemed to take forever, but eventually she rang back “Ok, I have done what you asked, where is this leading? I am getting a little freaked out”
“As I have told you the entire time, if you want to say no, please say no. I will still want to hang out, I will still think you are sexy, but I really think you will be amazed if you say yes……… I want to show you off.”
“SHOW ME OFF?!!” Z snort laughed “ what do you mean show me off? That doesn’t sound fun at all, who are you showing me to?”
“Wait wait wait a sec, please let me explain. I want you to go to an adult random chat site. Chatroulette, but dirty. I want you to turn on your camera, point it so your face is out of frame, but your exposed naked body is exposed. I want you to do that while holding your sign. You don’t have to do anything else. It is going to be an endless stream of men jerking off, looking for a woman doing the same. There are literally maybe a thousand men, for every woman, I assure you, you will be very appreciated”
‘That just sounds so skanky. I am not sure this is going to be my thing, but as it seems I have lost my mind, and you talk me into weird things with such ease, somehow, and now I am kind of curious…”
Z typed in the address, navigated through the entry crap, I watched her from my position in her phone, as she turned on the camera, and adjusted it so her face was out of frame, her nakedness on such casual display, I wondered if she remembered I could see her also, but she turned and smiled at me “Ok, about to hit start”.
I wasn’t sure how this would go, “turn off your mic on the computer, so you can speak freely to me on the phone”
“OH MY GOD, there is this guy waving at me, he is naked, and has a very small penis, and he is..oh god, next, hmm this man is handsome, and his dick is nice, ooops hes gone heres a new, nope, nope,nope, whoahh look at this guy, he is huge! And so skinny, that is amazing, he is waving too…”
“hold up the sign” I said “And spread your legs wide to show off that big pretty clit”
Z was clearly swept up in her new stardom, as she held up her sign and man after man extoled her beauty, and sexiness.
“ How is it going?” I called from the phone, “are they repulsed by your weird lady parts?”
“how should I tell this guy to worship me? hes asking. Oh wait, I know!” she chortled, then spoke as she typed “turn around and show me your asshole! …..Hes doing it, hes doing it!….. ‘now finger your ass hole you little bitch’, and..wait he says he has a dragon dildo.. oh my god oh my god, ‘yes use your big dragon dildo’ hey S, whats a dragon dildoooo OH My God”
“What is a dragon dildo!?” I was now shouting from the phone
“you gotta google this thing he is – oh my g- it is like a giant jelly dragon dick thing, and no fuckin way, it spurts cum, he just showed me, but it couldn’t possibly fit in his, yeeeoww it does fit, almost slipped in easily”
“wow, sounds like you are getting quite a show” “he just came, all over the place, he is asking if I want him to eat it? Is that like a thing guys do?”
“Um, isn’t my thing, I guess he does, what ever you want, Sex Goddess”
“Next, hey there is a girl here now. She is really pretty, and waving.”
“Wave back, have you ever thought about trying out being with a woman before?” I asked.
Z ignored me, and continued reading aloud the words she typed “wow you are so so hot! Your body is amazing!……….Hey S, She said the same back to me!….thank you, I am trying this for my first time. – At the encouragement of a friend. – I told him my pussy was ugly, and that I was ashamed of it, so wow, boys really get excited about pussy! I didn’t know that.”
“Are you still with the hot girl”
“yes, she asked to see my pussy, up close, I am going to show her, wish me luck”. I could see the joy on Zs face as she stood and approached the camera on the computer, and pointed it towards her slick black hair, put a leg up on the desk, and spread for the anonymous woman on the other end. I watched as she reached down beneath the desk and fished out her magic wand, and put it on low. The deep rumble was an unmistakable sound. Z stood pussy forward dragging the wand up and down the length of her labia, from ass crack to clit. After a few moments Z sat back down, then leaned forward to type “what are you saying, what is she saying” I called out
“She said something nice and I said something nice back, not for you, but she is gone now, hang up on the phone and come back to my computer”
“That was maybe the weirdest thing I have ever done, do you do that, are you one of them, those masturbating strangers?”
“ I used to, a lot” I confessed “but there used to be a lot more women on , and there used to be a few better sites. I am sure there still are better sites, I just don’t know where. I do love to masturbate with strangers, though, but you already knew that part” “Do you do it because you like to show off, or because you like to watch?” she asked “um, kind of both and neither. My earliest kink was voyeurism, and showing off came later, but I do love being watched, it is such a rush to get off with someone that is getting off watching you, but beyond the superficial, I am endlessly fascinated with what normal people do when they are horny and alone. Like your man with the dragon cock, is he married? Is he a member of the clergy? Do any of his friends know he fucks his ass and eats cum for strangers on line? I get a rush, prying out what people want to be seen but keep so deeply hidden, witnessing that moment when shame is dropped and they are free to act on desire.
“I don’t think I have ever met a pervert like you” Z smiled, “does it have a name, almost like perv-support?” and that set her laughing.
I sobered the mood “Z, I want to ask you to do something humiliating for me”
She cast a sideways glance, thought for a moment, and then said in a quiet, confident voice, “What would you like me to do?”
“What do you fuck.?” Z looked puzzled. I continued, “What do you fuck? I have seen the ass plug, and the magic wand, that you use for your clit, there is something that you fuck, that you haven’t shown me, get it now, please”
Z blushed a shade and then another, she opened her mouth, to speak, and then rethought, then went to speak again, but instead, stood up, went to her nightstand, and returned with a beautiful tortoise shell hair brush, a very expensive one. She held it guardedly, then reluctantly held it to the camera, “this is what I fuck,” using coarse words for my benefit “I have had it since I was 16”
“that is a beautiful brush, stand and show me how you spank your ass with it” Z hesitated looking very wary. I continued “ I have shown the whole internet what a slut you are, now it is my turn. So I am going to instruct you, and I would like you to listen, and do as told. I intend to watch you humiliate yourself, to spread yourself wide for me to use you as I see fit. Is that something you would like to do, Z?
“I think I would like that, yes” the words barely came out of her mouth.
“Now, I believe I have already asked you to stand and show me how you spank your ass with that brush” Z stood, turned, and straddled the chair, and bent at the waist, over the back of the chair ass to camera. The broad smooth back of the brush glided over her ass, as she seemed to hunt the perfect spot “how many”
“until I tell you to stop, I want to see your ass cherry red”
Z started slow and deliberate, a few seconds between each, not very hard, but the brush spanking continued to get faster and harder. I stroked my cock watching the color rise on her ass. “that is perfect Z, now spread your ass for me, I just want to see you standing ass open, for me. “
A few minutes passed and as she started losing her balance from the awkward position “Now sit back down, and I want you to spank your pussy for me, just like you did your ass”
In an almost fluid motion Z was back in the chair heels in position by the screen
“whap, WHAP,whap,whap,whap,WHAP” and Z screamed, and grabbed her pussy.
“please don’t slap any harder than what feels good” I got nervous,
Z growled back, “I,m not” and with that 3 more whaps.
“now I want to watch you fuck yourself, I want to cum all over that sexy body while you fuck yourself like a wanton whore, feverish to be fucked.
Z pushed her brush handle inside her and started fucking it rhythmically, using her hand she slapped her clit a few more times then reached down to find her magic wand again, and as she had clearly done many times before, Z pushed in to the brush hilt, put the vibe on low, and set it, as if on a table, against her clit, on the wide back of the brush. It took her both hands to keep everything expertly in place, and gyrations grew, “show me. Show me, show me. I. want. To. See. Your.cum. now” she said in changing tones.
I felt as if I had been hard for hours and watching her I stroked strong deliberate pumps and wailed as I shot white all over, There was so much, it was everywhere.
Z’s legs locked and her eyes rolled back as her entire abdomen flexed and contorted, as she moaned into a squeal, then silence
“ If I sent you a ticket, could you meet me in Miami this weekend”
“yes Z, that would be lovely”
I got to the hotel around noon. The exhaustion of travel had dissipated the anxiety over the situation, until this very moment. The doors parted, I walked in questioning my judgment
“S?” I turned and there was Z in person. “oh, hi” I smiled, then the strangeness meeting the person you have been having sex with, for the first time, “do we hug?” she wasn’t sure, an odd kinda of arm touching thing happened, and we both laughed. Anxiety subsided.
There was no question we head straight for the bar, me, luggage in hand. The hotel was gorgeous and we sat down looking over the beach.
Idle chit chat filled the space until half way into the first drink. “So, I want to switch the conversation, to why we are here. Is that ok with you?”
“Yes, its funny, if we are talking about it, I feel like this is going way too fast, and I need more time to process what is going on, then I remember 41 years is a lot of time and it will never get easier for me to do this, than it is right now.” Z took a deep breath and a stiff pull from her drink ”So yes, lets talk about why we are here.”
“do you have an idea of what you would like to happen?”
“yes, and no. I mean I have imagined a lot of stuff, but I don’t know how to explain most of it, and I feel like anything I say will sound silly. What I would like, is for you to tell me what to do” Z perked up “I don’t mean be bossy, I mean an instructor. Would you teach me?
Honestly, I had never been so flattered. “I have a plan I want to suggest, you tell me if you like it. I am here for 2 nights, which means we have today and tomorrow. I think the logical first step, is to go back to the room, I will shower and wash the travel off, then come into the room naked, and let you explore my body. I will let you do whatever you like and ask all the questions you have. Then take it from there. What are your thoughts? “
Z, looked me over, finished her drink handed me a key card and said “I am going to shower first, I need 20 minutes- room1206” and with that, she walked to the elevator and was gone.
I walked into the room, and she was sitting in her robe at the end of the bed, “the shower is all yours”
“I will be back in a sec” and after a few minutes I emerged, clean, smelling nice, teeth brushed, and stark naked. “are you ready for me, Z?”
The mix of excitement and embarrassment showed in her blushing laugh, as I walked close to her, still sitting at the end of the bed, dick at eye level. “so… I can just touch it, do I need special instructions, I don’t want to hurt you by doing it wrong”
“It is pretty durable, teeth and fingernails, keep away, like any other skin, and squeezing too hard will hurt eventually, ”
“how long does it take to get hard?”
“if you wanted to start kissing it, I bet I could show you”
Z reached a robed arm out and cupped my balls, she rolled them in her palm, leaning in close to observe as my cock started to swell. I stepped closer and with her free hand she squeezed my now mostly hard dick, and kissed it square in the middle of the tip. Then again, followed by a flick of the tongue, and a few more licks. She apprehensively wrapped her lips around the tip and focused intently as I gently pushed in a little deeper, until the head of my cock was fully in her mouth.
I stood still and fully erect as she contemplated the penis in her mouth, after a few moments “will you lie on the bed for me?” I obliged happily. Z stood, and let her robe drop for the first time.
“oh my god, you are stunning, are you doing ok? you look great, I am really happy to see you naked”
“for the moment, I am doing fine, but if we make a big deal about it…
Z lay down next to me, then climbed on top and wrapped herself around me, I put my arms around her and we lay like that for a while. It was intimate, it was comforting, and although I stayed silent about it, as I lay there, holding her, I could only think about how difficult it must have been to go 41 years without touch. Quietly I held her naked body, for a while longer.
Eventually Z’s hands started to wander. “I like your fur” she started “rubbing my chest, and you are much bigger in person that I thought you would be.”
“Really, how tall did you think I was?” “oh I don’t know, not this tall, also, that means your dick is bigger than I thought, too. I am not so sure I am going to be able to do a good blow job, and anal is definitely out. I hope that is ok. Is that too forward”
After I stopped laughing “ we will work with what we got, no anal is a fine rule for a first date anyway”
Z rolled off me, “spread your legs for me” I complied, as she got between them to examine my member from a different angle. “Show me how you do it when you jerk off, jerk off for me”
Z rested her head on my inner thigh as I started stroking, coaxing my cock back to rigidity. She watched with intensity as her hand held my balls, and eventually slid my hand out of the way and took over with out missing a beat. I stopped her after not too long, “would you like me to touch your body, for a bit? Come lie face down, here”
Z did as asked. I poured a small puddle of coconut oil in the small of her back, and rubbed it in, all over. I massaged and rubbed her ass, allowing my fingers to just graze her labia from behind, a few more teases and, impatient, Z opens her legs wide, and I slide my hand over her wet and swollen pussy, ad she gasps and says something into the pillow. “On your back” I whisper to her, and she rolls in place, now on her back, knees bent, legs wide, open for me.
I start again with my hand, using my middle finger to just glide on the tip of her huge swollen clit. Tiny tiny circles, then, sliding my hand down, pushing a finger inside.
Z gasps and grabs my arm, I freeze ‘don’t stop, please don’t stop, don’t stop, but I do. Greedy for more she protests, then as I climb, face first between her legs, Z catches on, relaxes her legs open further and lays back, as I finally see her beautiful clit in the flesh.
I spread her sweet pussy with my tongue, before moving to her swollen button, immediately I am sucking on her clit, keeping suction between by lips and tickling gently with my tongue. I gradually pick up speed and insert 2 fingers inside her working in counter time to her gyrating hips. Her moans got louder, until her thighs locked around my head, pushing me harder into her pussy as she shuddered and eventually released me to breath again. Feeling like a champ I lifted myself up to Z crying softly.
“are you ok, Im sorry, you should have asked me to stop, I thought things were going good…..”
“I need you to fuck me, right now”
I knelt between her legs, rubbing the head of my cock against her clir, and down to her pussy, spreading her slightly, stroking my self a bit until I was rigid, quickly slid a condom on and pushed in. I leaned in and kissed Z for the first time, gently. Still with tears running down her cheeks, she kissed me back, she ran her hands up and down my body , and after some gentle back and forth, I pushed slow and steady, until I was all the way inside.
Z whispered, “don’t move, I just want to feel this for a minute” and I stayed as close to still as I could, deep inside her, but instinct over rode self control and it just felt too good, fucking her.
‘Ok, ok, this feels different, than I expected,” the tears had passed, “its all the skin. I mean , oh my god this feels really good, fuck me hard, I dropped out of teacher mode, reached down and grabbed her ass with both hand and started steady fucking, Z responded like she was born to fuck, grinding in rhythm , I started getting closer and closer “Pull out I want to watch you cum, cum all over my face” she said
a final thrust, I pulled out and slid the condom off in time to cover Z’s abdomen, with cum. She watched shamelessly and her eyes got wide watching me orgasm.
It was over, V-card no more. We lay quiet for a while, then Z, ass naked and covered in cum, walked out on the balcony in the middle of the Miami afternoon and shouted “I AM NOT A VIRGIN!” walked back in, “I am going to shower, then we are getting drinks”
Source: reddit.com/r/Erotica/comments/d53lfw/my_first_time_helping_an_adult_virgin_encounters
Beautiful first time xx