It started because of the cancelled flight. None of it was planned.
I had been overseas on an extended business trip, and the return flight was bumped due to 'technical problems'. I'd rather be bumped for twenty-four hours than fall out of the sky, but it was still irritating.
I was tired, I was grumpy and I had been looking forward to getting home - not that, other than my own place, there was much to look forward to. At thirty-five, I was mostly single, living alone in a nice house I'd bought after a particularly successful second year running my own business. Respectable area, mostly families, pool, etc.
We were put up in an airport hotel, and after unpacking the immediate necessities and having something to eat at the bar, I retired to my room with a couple more beers and my laptop. Honestly, I had good intentions of finishing my expenses and doing some work, but after ten days of work, I couldn't face it.
As I started another beer, I decided to click on one of those video chat sites - the ones that let you 'chat with a stranger' and 'be whoever you want to be'. I'd been tempted before and never had. But I did this time. Wearing a t-shirt and pants, I hooked up the laptop so I was visible from my chin down.
I soon got the hang of it, and there was a lot of clicking on and on. I think I saw more male genitalia in the first twenty minutes than in the entirety of my life to date. Don't get me wrong, I don't mind men who like dick, but the only dick I am interested in is my own!
And then it happened. On the screen appeared this absolute beauty. I could see her thigh, arm, and neck, the rest was either covered by a purple sheet or off-camera. She looked amazing, with alabaster pale skin, curved in the right places, and here with the same thing in mind. From what I was seeing, I estimated that she could have been anything from sixteen to twenty-five - and I admit it, I didn't ask.
I said hello and introduced myself, she did the same. Her name was Rebecca and she told me she was from the same state as I was. We chatted a little and it was when I commented on the purple sheet and asked what was under it. Her simple reply was: "Do you want to see?"
I was schoolboy keen in my reply, telling her yes. And man what a figure - she had beautiful full breasts, slightly uneven in shape & development, full hard nipples, and a trimmed dark bush. Her stomach wasn't flat and it was enticing.
She started by playing with her fantastic boobs, pulling the nipples, clearly turned on. Moaning as she was pulling them and playing with them. I started telling her what I would do to her if I was there - sucking her nipples, kissing her neck, putting her legs over my shoulders, sucking her clit, finger fucking her, etc.
It was pretty descriptive, really erotic and Rebecca was loving it. Although she wasn't speaking, I could hear the squelch of her wet pussy, and her moans as she got closer and closer to orgasm. She was close, writhing around and needing to cum. She stopped and shifted position, moving so that she was facing the camera with a pillow bunched under her between her legs.
As she started to ride the pillow she typed, "May I see you please, Sir?"
I adjusted the camera, lowering it, so she could see my rock-hard, cut eight-inch penis. The veins were showing it was so hard. As I stroked the length of my dick with one hand, I cradled my heavy balls in the other. Rebecca rode her pillow, leaning in with her tongue out. I could hear her moaning and panting. Breathing harder and faster.
I told her to imagine she was riding my dick, her boobs between my lips and my hands on her ass cheeks, fingers exploring, the occasional slap to her ass cheeks. She started moaning harder and faster, swearing some in a husky lust-filled voice.
"Fuck yes, I'm gonna cum. Oh, Daddy make me cum!"
I could see her press into the pillow, cumming hard. It was one of the most beautiful and erotic things I have ever seen.
Still visibly shaking from her orgasm, she leaned forward, her arms cupping her wonderful breasts, pushing them together for me "Thank you, Sir, now I want your cum. Cum on my tits and mouth."
I stopped typing and concentrated on my hard dick. Looking at her, it didn't take long for me to cum. Always a quiet cummer, I was breathing harder as I watched Rebecca still grinding into her pillow, encouraging me.
With a gasp I came hard, shooting rope after rope of cum towards the camera. Rebecca jumped, grinding down into the pillow simply telling me "I'm cumming again" as she rode that lucky pillow.
We both stayed where we were, recovering as our breathing settled. My dick, sticky with cum, and her pillow soaked through. My eyes feasted on this beautiful young lady in her post-coital confident pose.
We chatted a little, and I asked if there were ways to 'chat' again - we agreed on swapping Skype IDs and then she asked where I was from. I repeated the state, and she delved further, asking where about, etc. She named a medium-sized town but didn't seem too familiar with it. I told her the truth about where I was living. She went pretty silent, before telling me she knew it.
I didn't probe further, but she said she had to sleep some and thanked me. She said to check my Skype when I landed etc. We both hung up and went to sleep satiated.
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For various reasons, I didn't get to check my Skype until I got home and unpacked. I felt nervous logging in, part of me wondering if I had dreamt the whole thing. But there it was, a message from Rebecca asking how my flight was and how jetlagged I was.
She had also attached two photos of herself - one was a body shot and the other was a simple photo of her pubic mound. I could see how wet she was as her puffy labia were protruding and her clit had escaped its hood. My cock swelled as I looked - fuck. this girl had me enticed!
The message following was simple. "Can I feel that cum land on me for real, sometime soon, please?"
I was nervous but also entranced. Taking a photo of my now hard dick, I sent it back with a simple "Friday?"
Almost immediately, I got a response. "You're back, I was starting to worry you'd ghosted me. I've never done this before, but I want to. I can make Friday work. How about the Motel on I-90," This girl wasn't messing about.
I had never met anyone like this before, but I desperately wanted to. My reply was clear. "Do you want me to collect you, or meet you there?"
Rebecca replied, "I'll see you in the coffee shop at noon. I'll have my hair in braids and be wearing a blue check dress."
She had thought this through, we were all in and I was excited. Friday was only the day after tomorrow, but I couldn't wait. My only reply was to add. "Leave your panties at home." Before signing off with a kiss.
I busied myself with post-trip laundry, paperwork, sleep, etc. I also jerked to her two photos and the third one she sent Thursday night of her with her ass to the camera. The message she sent was, "Save some of that cum for me, don't waste it." I couldn't help it. Last jerk to her, and I stopped.
Surprisingly, I slept well Thursday night, waking up rested. I was nervous and excited, telling myself to calm down. Work took up some of the morning, before I took another shower and drove the short distance just before noon.
Adjusting myself and taking a deep breath, I walked into the coffee shop, looking around. At the other end of the coffee shop, by the window looking out onto the motel, was the only coffee shop occupant. She had jet-black hair in braids, and she was wearing a blue check dress. As I walked over slowly, I could see her head was down looking at her phone.
Standing behind her, not too close, I could see her looking at her Skype account on her phone. I cleared my throat, saying, "Were you expecting me to cancel?"
She put the phone down and slowly turned around. As I looked at her, we were both smiling. They were smiles that quickly changed to embarrassed questioning. Rebecca was my seventeen-year-old neighbor, who I knew as Becky, and whose mother I had dated a few times the summer before last. Fuck!
Looking her up and down, I recovered quicker than she did. "Fuck, Becky, is this what I think it is?"
Her beautiful face went a deep shade of crimson, from her chest to her forehead, my eyes unable to stop themselves from looking her up and down. She nodded as she stood up. "I had no idea it was you, Sir."
Standing there, looking at this exquisite teen, whose body I longed for, and who I could still picture naked and writhing, made my cock twitch in my pants. I took her hand and sat down, pulling her with me.
She looked at me. "You have to understand, that was my first time on that site. And this is the first time I've ever arranged to meet someone. There was such a connection. And, oh God, those photos. Please don't tell Mom, she'll kill me. And you dated her. Oh fuck." As she went on.
I took her hand, squeezed it, looked around quickly to see if we were being watched, and kissed her on the lips to stop her babbling.
It worked, as she stopped talking and pressed into me shocked, kissing me back. Pulling away, we looked at each other and then around to see who was watching.
My fingers were stroking her thighs, as I said, "It's ok, I won't tell anyone. Especially as I would be in the same, or more, trouble."
I could feel her goosebumps raising on her legs as my fingers stroked her firm skin. Squirming lightly in her seat, I asked, "What excuse did you give to skip school?"
Giggling, she said, "Mom just went away to see Grandma until Sunday, so I'm staying with Jenny. She's covering me. The school thinks I am sick."
Taking her hand, I squeezed. "What are we doing, Becky?"
Wide-eyed, she told me. "Going to room five, I hope. I'm glad it's you, I had a crush on you since you dated Mom. I knew you stayed over a few times."
Spreading her legs, her dress riding up, her firm pale thighs visible, she leaned in, whispering "I won't tell anyone, I promise. And I left my panties at home, just like you told me to."
Smiling, she scooted back and stood up, shaking her butt as her dress fell lower, she walked off. With a rock-hard dick and a deep sigh of 'What am I getting myself into', I got up and followed up.
We went around the back of the motel, and up to the second floor, Becky letting us into the room. Closing and putting the chain on the door, I stood looking at her, framed in the light.
Walking towards her, I pulled her towards me. "Are you sure this is what you want, I dated your mom and I am twice your age, a stranger?"
Moaning with desire, she pushed her 5"6 frame into me, pressing her body against me, head tilted up. "More than anything. I am SO glad it's you, not some weird stranger."
Kissing her deeply, and with suppressed desire, I lifted her into my arms, holding her close as we kissed passionately and I carried her to the large bed.
Laying her down, I straddled her, my 6"3 frame encompassing her, as our tongues jousted and our bodies writhed. Moving from kissing her lips to kisses on her neck, I could feel Becky react, her breathing getting deeper and faster.
Kissing down her sexy young body, I pulled on her nipple through her dress, seeing how hard it was. Flicking it, I looked at her. Feeling Becky writhe, I pushed the hem of her dress up as I kissed lower. She splayed her legs as I pushed the dress up over her thighs, looking at her. She was indeed pantyless.
Stopping, I looked at her. Firm pale thighs, crooked and raised, with her full dark bush on display I could see her wet pubes and her puffy labia were starting to show. "You look sexier here than on any camera." I snapped a quick photo and showed it to her.
Putting my phone away, I decided I needed to pleasure my young lover. Pushing her legs back, her sweet pussy was spread wide with the dress around her hips. The stubble from my cheeks was grazing her inner thighs as my tongue snaked around her wet open pussy. I could hear her moaning, I could smell her sex, and I could see how wet she was.
That first touch of my tongue was electric. I maneuvered the tip of my long tongue around her open holes and puffy lips. Before parting her swollen lips, and tasting her for the first time. So sweet and hot.
Holding her spread wide, my tongue moved from flicking her throbbing clit, down her pink open slit, around her puckered pink asshole, before plunging into her open pussy. My nose pressed against her clit, I used as much of my tongue as I could to tongue fuck my young lover.
Immediately, my face was covered in her hot sweet wetness. My hands were massaging and working her butt and thighs, I could feel Becky writhing as I tongue fucked her.
Sliding my middle finger into her slick tight pussy, I finger fucked her slowly, as I moved, kissing her. After initial hesitation, she kissed me passionately, tasting herself from my tongue as her tight little teen pussy gripped my finger.
She was moaning into my mouth, I knew she was close.
Leaving her delightful face, I spread her legs wide. I took her hard throbbing clit between my lips and I let my teeth rake over it. Becky writhed and groaned in pleasure, she liked that! Sucking her clit hard, I felt it throb as I used a finger in her tight teen pussy. She was gripping me as I moved in and out.
Her pussy juices were flowing freely, as Becky moved to meet my fingers, trying to get more and more in. Breathing hard, in a raspy voice.
"So close."
"So good."
"Yes, Yes, YES."
As she moaned and writhed, cumming on my face, with a finger deep inside her tight little pussy. I drank all her juices in, my finger not moving but still inside her spasming pussy,
As her breathing calmed, she pulled me to me. She looked at me, still dressed. My shirt was soaked. "You need a new shirt, whoops."
As she kissed me, she said, "Thank you, that was the best ever, but I want to see that huge dick of yours for real."
Sitting up, as I watched, she pulled the dress over her head. Her fabulous firm boobs were on display, she was naked. Cupping them, she looked at me. "Enjoying the view?"
I nodded, standing. As I feasted on her beautiful teen body, I pulled the wet shirt over my head and dropped my pants. I stood naked next to Becky as she smiled, licking her lips.
She crawled over the bed towards me, her breasts hanging freely, as she reached to cup my hard dick. Stroking it back and forth, my dick was eye level with her face, as my dick jerked up and down at her touch.
"It's so much better, and bigger, in person."
As she leaned forward, the tip of her tongue gingerly reached out to lick the bulbous head. Her tongue was very velvety and welcoming.
Groaning at her touch, my dick swelled more as she sucked it between her lips. Just the head was in her mouth, but it felt amazing.
My dick in her mouth, Becky pushed me back so I sat. In one swift move, she wrapped her fabulous breasts around my dick and started to suck more into my mouth. Fuck this felt amazing, how could a teen give better head than her mom?
My cock was swollen and huge in her mouth. My balls were tight. Becky wasn't deep-throating me, but she had over half of my nearly eight inches in her mouth.
She was panting as she sucked, the sound of slurping filling the room. I was breathing hard, trying to control myself.
I had to stop her. I pulled her up and off my dick, as she nervously asked, "Was it not ok?"
"It was perfect, probably the best blowjob I've had, but I want to fuck you, I need to fuck you."
Confidence returned, her face lit up by a smile, I pulled her towards me to straddle me in the chair. Looking up, one hand on her hip, the other on my dick, I kissed her as I stroked my dick against her wet pussy.
Straddling me, I eased my swollen dick head, still wet from her mouth, into her sweet and tight, teen pussy. We both groaned as we felt me enter her.
Head buried in her breasts, sucking a nipple, one hand on her hip, Becky slowly lowered herself onto my shaft. Not moving, I knew I had to let her go at her pace. Inch by inch she lowered herself onto me. I felt wrapped up by her velvety wetness, so tight.
I could feel Becky breathing out, trying to relax her body, as she lowered herself along my shaft. Inch-by-inch, I filled her. Pube-on-pube, her nipple throbbing in my mouth, I pulled off and looked up at her, kissing her lightly on the lips, I asked, "Okay?"
"Yes, it's amazing. I feel so full."
My dick grew inside her, swelling and filling her more, as she groaned, "Oh wow."
With my hands on her hips, she started to move. Up and down, riding my long dick, Becky started to fuck me. As she moved, her tight tunnel loosened some, able to ride the shaft.
Deep inside her, hands on her butt cheeks, I lifted us up, pressing her against the wall as I wrapped her legs around me. Thankful for strong stomach muscles and legs, I moved my hips as I drove my dick in and out. I could feel how much Becky was enjoying herself, as her juices ran down my thighs.
It felt amazing, so tight, so hot, so wet and so fucking great. I knew I shouldn't be fucking this teen, but I was so glad I was.
Moving from the wall to the bed, my dick popped out of her. Glistening with her wetness covering it, she looked over her shoulder at me as she got on her knees. "Fuck me from behind, hard. Please."
Never one to disappoint a lady, I pulled a pillow under her and between her legs, pressing her hand against her clit as she rubbed. I think it reminded both of us of how she came when we were camming.
Legs spread, pussy wet and open, her clit and pelvis pressing against a pillow, I gave her ass cheek a quick slap and pushed my hard dick into her from behind. We both groaned, loudly.
My balls were tight and full, my dick swollen. Becky was slick and tight. We knew that we were both close.
One hand on her hip, the other on the small of her back, I did what Becky asked. I fucked her, and I fucked her hard and fast. The entire length of my dick working in and out, balls banging against her butt cheeks.
The sound and smell of sex filled the room. Becky had her head down on the bed, her hand under her on pillow rubbing her clit.
"Fuck, yes."
"God, so full."
"So close, fuck me."
Breathing hard, panting as I fucked her, moaning I told her, "I'm close."
"Cum in me, I want to feel it."
As I drove deep inside, balls against her, I exploded inside my sweet and sexy teen lover. Balls emptying, I filled her. That set Becky off, cumming hard with my dick inside her, she screamed into the bed as she came, her pussy pulsating and milking every last drop from my balls.
We stayed where we were, panting and calming down. As I felt my dick start to soften a little and Becky stop spasming, I pulled out of her, flopping on the bed next to her, reaching to kiss her. Laying over me, she kissed me before propping herself up on an elbow on my chest.
"That was amazing, better than I ever have imagined. One to remember forever, thank you for being my first and making it amazing."
Open-mouthed, not having realized, she smiled as I started to say something, kissing me passionately. "I need a drink and shower before we do some more exploring. What do you think?"
Sliding off the bed, naked and beautiful, I looked at her thinking of another wonderful mess I'd gotten myself into.