The Time I Helped [M]y [F]riend Scratch An Itch

The trade show was in the Bay area, a long way and a few time zones away from my home base in Florida. It was the kind of dog and pony show where you hear some talks and browse a floor full of product booths all staffed with eager company reps trying to drum up as many contacts as possible. My employers thought it was a good idea to send me, since I’m in my early 50’s and I’ve seen it all and I’m good at weeding out the bullshit in a sales pitch.

The bright spot in all this was that I was getting time to hang out at the show with my good friend Sara. She lived an hour or so away, and I’d convinced her to play hooky for a few days. We’ve known each other from work since our kids were little, but somehow had never met in person. That didn’t stop us from keeping in touch constantly and we have one of those friendships where we can (and do) tell each other anything and everything. Sometimes after a few glasses of wine on a lonely evening our chats would get flirty, but it was all in good fun and we’d be back in the Friend Zone the next day. Sara had even seen me naked, heck, after a few drinks the nudist in me comes out so it was bound to happen. I’m older and I don’t go to the gym every day so I need to lose some pounds, but I’m comfortable with myself. Sara is about my age and a shorter blonde with an infectious smile.

​

I was happy to have that smile for company as we walked the show floor collecting handshakes, swag, and business cards. By the time the keynote dinner rolled around, the time difference from the east coast and long day of travel had started to catch up with me. I started making whispered jokes about the speaker to her as a way to fight off the yawns, and Sara would giggle and elbow me to stop it. This only encouraged me, because this dude was rolling out the business buzzwords like his job depended on it. Maybe it did. When the dinner wound down and we were mercifully getting ready to pack up our swag bags, I asked the question that had been on my mind all afternoon.

​

“So, did you decide to stay over, or are you driving back tonight?”

​

“It’s tempting. I’m not looking forward to the trip home and turning around to come right back in the morning. I don’t know.”

​

“Hey, my room has 2 beds and we can just relax and chat instead of you fighting traffic. Besides, I’m exhausted, I’ll probably be asleep as soon as we get there.”

​

“Don’t laugh, but I have a box of wine and some snacks in my car…” she grinned, looking me directly in the eyes. I instantly felt a twinge of blood flowing down south that hadn’t been there before.

​

“Sold!” I said, blushing a bit.

​

As we fetched her car from the garage and I let her drive to my hotel, things calmed down again and we were quickly back to easy conversation about some old co-workers and wondering what they were up to.

​

Back at the room, I’d like to say I had her pressed up against the door and we were passionately making out the second the lock clicked, but I was being on my best behavior. We could be flirty sometimes and it was a huge mutual confidence boost, but down deep we both knew taking things farther could be a train wreck.

​

So instead we drank box wine from hotel coffee cups, and I put on the Food Network while we sat close on the strangely-patterned sofa. The awkwardness fled again as we chatted about the goings-on in the Chopped kitchen. I was getting very relaxed and almost heavy-lidded. We were well into the second generous cup of wine, pondering what would happen to the guy who forgot an ingredient, when it happened.

​

“Hey!” she tugged at the side of my company-logo polo shirt. “For someone who always goes on about being a nudist, you’re way over-dressed buddy.”

​

“Y-y-ou’re not wrong.” I stammered, feeling more awake instantly. “Is that OK? Not too weird?”

​

“Really? I’ve seen your boy bits before you know, it’s only weird if you make it that way. I trust you.”

​

“Right, OK.” I said, slowly getting up. “What about you?”

​

Her eyebrow went up. “Trying to get me naked?” she said with a growing smirk.

​

“N-n-n-ooo, I mean you’re still wearing your trade show clothes too.”

​

“Relax dork, I know what you meant.” she laughed as she unzipped her overnight bag on the bed and started rummaging through it. I was over by my bed and stripped off my shirt and started undoing my belt. I’ve been nude around platonic friends before and it’s usually no big deal, but this felt different somehow. I took a few subtle breaths to take some of the tension out of my body.

​

“Crap.” Sara said as she looked up from her bag. “Where was my head this morning! I didn’t pack for this. Do you have a t-shirt I can borrow?”

​

I dug a soft-stretchy running shirt from my bag and tossed it over, nervously. “Always prepared!” I turned slightly away from her and counted off 1-2-3 in my head, then slipped off my dress pants and boxer briefs in one movement, folding them nervously as I wondered if she was watching me.

​

“Right, that’s better. I’ll go get changed,” she said, heading to the bathroom. I grabbed a spare white fluffy towel and set it out on the couch to sit on. As I sat back down on the couch, I glanced at my dick and was thankful it was not awkwardly sprouting a boner. I chalked it up to nerves, and that little voice in my head that that was still trying to keep this boat between the channel markers. I inhaled slowly and whispered “just buddies” to myself as I settled back and tried to get my bearings on the TV show again.

​

Sara came out after a few minutes, and my jaw fell somewhere south of my knees. She was wearing my soft, thin, t-shirt and white cotton panties, and nothing else. I could tell by the way her mature breasts swayed and the fabric peaked on her nipples that she’d dispensed with her bra as well. She was so sexy-cute in my shirt and my mind started racing with thoughts of feeling those soft mounds swelling in my hands and my lips gleefully nibbling along the waistband of her panties. I knew from a few selfies that her nipples were succulent and pink. They’d feel so good against my tongue as I flicked and suckled them gently.

​

“You’re not getting this shirt back, you know. Too soft.” she said, snapping me out of my fantasy.

​

“Nice headlights!” I laughed, hoping to deflect her attention away from the erection I could feel rising in my lap, unable to be stopped.

​

“Dork. It’s just cold in here.” she rolled her eyes, and grabbed our coffee cups to go pour more wine. As she faced away from me and filled the cups I was mesmerized by the sight of her ass peeking out a bit from under my shirt. I got that glimpse of pussy from behind in panties that just slays me, and I knew I was done for.

​

Like the hapless hero in a British comedy show, I decided to just pretend that I was oblivious to the Leaning Lower of Penis that had quite obviously been erected the moment her back was turned. It was not a good plan, but it was the only one I had.

​

Sara turned to face me with the coffee cups full of cheap wine and her eyes of course went right to my cock. If she was mad or shocked, it didn’t show, but there was a moment of silence.

​

“Well, hello there. Someone is frisky!” she laughed, and sat down next to me again, close enough that the warmth of her was making me blush.

​

“I’m sorry…it just happened…” I started to blurt out.

​

“It’s OK,” she interrupted, her voice soft and thoughtful, “I’d almost be offended if you weren’t…like that…right now.” The silence crept back in for a moment as she handed me a cup and seemed to be looking right at my lap but also off into the distance. Her head jerked towards the TV. “Marzipan fruit in an appetizer? That’s ridiculous!” she laughed.

​

And there we were, back to our comfortable friend zone, despite the absurdity of me being next to her naked and her looking irresistibly edible. My head was a jumble thinking of all the places on her body I wanted my mouth to be, and writing an expanding catalog of positions I wanted to fuck her in. Slowly my arm went around her and my hand found her waist. She shifted so her head was against my chest, and could feel her breaths heavy against my skin. “I’m glad we can be like this with each other,” she whispered.

​

“Me too. Whatever this is.” I said as I brought my other hand up to graze her cheek. She would not look up at me.

​

“We can’t have sex you know. It…it just is…complicated. You know.” she said, as her hand went to my stomach, firmly. My breath caught at the sensation, and cock twitched visibly with each heavy beat of my heart.

​

“I know. It’s OK.” And maybe it was. I had just gained enough mental images for my spank-bank to last me the rest of my days.

​

Still not looking up at me, her hand slipped lower to the base of my manhood. “Jesus, it really looks bigger in person.” I lost the capacity for speech as she tried to close her fingers around my girth and gave my skin a gentle tug. “It always amazes me how soft penis skin feels…” her voice trailed off. My hand slipped down from her waist and palmed her curvy ass over her panties. The sight of her small hand on my cock brought forth the first few drops of pre-cum that had been building up.

​

“Fuck.” Sara cursed. “OK, we can’t have sex, but it’s been too fucking long, I need to feel a man inside me…”

​

“I could go down on you…” I said. Her hand still stroking me slowly, bringing up another pearl of pre-cum with it each time, like she couldn’t stop doing it if she wanted to.

​

“I’d love that but…it won’t scratch this itch.” I could feel her heartbeat everywhere and her breaths were choppy. Her legs were clenched together and tense. Her hand paused at the top of my shaft as her eyes caught a warm drop escaping from my slit and sliding down to settle on her finger.

​

“How do we do this? How do we not do this?” she pleaded.

​

My mind was a whirring blender of every possible emotion as I struggled to identify the mystery ingredients spinning the tale of what could happen and what should happen. I wanted to fuck her brains out, but not at the cost of regrets.

​

“Sara, ” I said, “look, we’ve had a lot of wine and it’s been a crazy day, and…”

​

“Don’t you chicken out on me! I didn’t come this far not to feel this thing in me…feel *you* in me…” she squeezed her hand on my cock almost angrily. “I just don’t know how to do this. We can’t have actual sex.”

​

Most of the blood normally feeding my brain had moved elsewhere, which explains why I said “OK Sara, maybe I could just…uh…be inside you and not do anything else?” As soon as I said it, I knew it was the stupidest, most blue-balling thought I’ve ever had.

​

She looked up at me, eyes wide. “What?! Really?!”

​

I guess in our drunk and horny state, anything that ultimately led to my cock being buried in her soft pussy made perfect sense to both of us, no matter how shoddy the justification.

​

“Look, OK. No kissing. No stroking. No looking into each others eyes. No romantic junk.” she said, with authority and breathlessness.

​

“Can I at least go down on you? I’m kind of girthy, I want to make sure you’re ready…”

​

“Jesus, I’m as creamy as a damn dairy down there right now, I don’t need any more foreplay!”

​

“OK Miss horny kitty,” I laughed, “How about we just go spoon in bed? You won’t have to look at me and you can touch yourself until you’re all orgasmed out.”

​

“You won’t mind?”

​

“I’ll be fine,” I said, not really believing it. I wanted to be inside her though, as much as I can remember ever wanting anything. I’d figure out the details later.

​

She jumped up and pulled me by my hand over to the bed. I smiled and pulled the covers back, and faced her with my hands on her arms, sliding down. Her breath caught audibly as I reached her hips and started to peel down her panties. Her nipples were pebbled so hard they were taunting me through the shirt, begging to be given attention from my open mouth.

​

She backed up a step, looking down shyly. “I’ll take care of these, you get in bed. No looking.”

​

I didn’t argue. I’d do a handstand on a stack of Lego bricks right now if that’s what she wanted.

​

As I slid into the sheets, I laid on my side facing away from her. I heard her panties sliding off her legs and swear I could practically taste the scent of her arousal in the air. I wanted to bury my face in that delicious triangle and breathe it all in, if not now, then very soon.

​

The lights and TV quickly extinguished themselves. From the dim shine of outside through the curtains I could see her, still wearing my shirt but quite delightfully bottomless as she moved around to the other side of the bed and slid in with her back facing me.

​

Sara settled against me and wiggled her ample butt…my cock was throbbing almost painfully against the heat and the warmth of her pussy and her juices were making me slippery to the point I could feel every little movement. She was teasing the throbbing head of my dick with her creamy warmth, and I wouldn’t last long at this rate. I grabbed her hipbone firmly, and whispered in her ear, “Hold still sweetie. That feels too fucking good and I need to go slow.”

​

She nodded quickly against me, and I could tell her hand had already found its way to her folds and was stroking through them. I wished my fingers were there giving her pleasure instead.

​

I nudged her leg up a bit and guided myself to the angle I was looking for, struggling to hold back the urge to just bury myself into her in one deep stroke. “Mmmmf…so good” she said as I paused with the thickest part of me resting just inside her entrance. She was tight and soft and warm…I felt tremors of her muscles squeeze against me as her fingers worked her slick folds. She was practically purring and I could tell it would not take long and I slid in a fraction of an inch more at a time.

​

“Oh!” she said as my hand moved from her hip to her breast, catching a nipple engorged and perky under the soft fabric. Over the cliff she went, shaking and moaning and tightening her internal muscles so hard on me that I thought my cock might get pushed out of her. Her hand pressed on top of mine as I cupped her breast and I stayed still as she lay there feeling the aftershocks of a long overdue orgasm. As her pussy relaxed it felt like she’d gushed warm honey around me. My hand returned to her hip, holding it steady as slipped in as deep as I could go in this position.

​

I rocked back and forth ever so slightly, and bent her body forward, craving that magic angle. She moaned again and the muscles of her pussy contracted rhythmically, drawing me deeper. This girl never skipped Kegel day, for sure.

​

“Coming…again…” she purred, and I held myself still, afraid of letting myself explode into her and putting an end to the exquisite massage her vagina was giving me. This continued until my cock felt like it had swelled beyond belief, filling her up and anchoring me deeper into her body. Every movement, every breath, every beat of her heart resonated in my engorged member and we became joined as a single organism in that way that only exists in moments such as this.

​

More shudders and orgasms followed and eventually her movements slowed. I could feel her body going slack. My arousal continued to throb within her though, and I could no longer hold back. I kept my tortured cock inside, but rolled her gently face down and I was astride the back of her thighs, pushing the shirt up to admire that sweet ass. “Oh!” she said sleepily, coming around to new sensations of the “prone bone” position.

​

I pressed my upper body down to meet hers. “I’m going to fuck you now, Sara,” I growled in her ear, punctuating my intentions with a strong thrust of my hips.

​

“Oh god, fuck me…” she surrendered.

​

I sat back up and began thrusting hard and deep as I massaged her lower back and fleshy ass cheeks with my hands. I was feeling that delicious pressure on the sensitive underside of my penis and knew I could not last long like this. Her primal moans let me know she was in the throes as well. Every stroke out left me immediately wanting back in, and I leaned forward, my body completely above hers. I mercilessly bounced my hips against her ass and back out, over and over, my abs burning with effort. I delighted in the feel of her moving back to meet my invading thrusts. I wanted to distract myself and make this last longer but it impossible. “Fuck! I’m going to come Sara!” I roared.

​

“Don’t you dare pull out!” she moaned in an exasperated tone I barely recognized.

​

That was all it took. I spilled rope after rope of pent up sexual tension into her, deaf to the guttural sounds she was making or the weight of my body on top of her, pushing her down hard into the mattress.

​

After a time, I summoned enough energy to lay back to my side and gently pull her limpness into a spooning position, my arms wrapping hers in the kind of deep, sleepy, cuddle that’s only possible after intense lovemaking.

​

“You’re still not getting this shirt back,” she whispered, as sleep claimed me.

​

​

​

​

​

​

Source: reddit.com/r/gonewildstories/comments/b4kglb/the_time_i_helped_my_friend_scratch_an_itch