I’ve always found mutual masturbation highly erotic, and this experience occurred several years ago when I was in my mid-30’s. I worked in radio for a lot of years and hosted many live events. This particularly evening, I was scheduled to do a live Friday Afternoon Club at a bar about an hour away. The events in smaller towns tended to be a pretty big deal to the locals, and were usually pretty wild.
The salesperson for this particular bar was a woman named Tammy. She was in her mid-20’s, about 5′ 10″, athletic, with long sandy hair. From past events, I knew she liked her vodka and could get pretty crazy. She lived with her boyfriend and he would usually accompany her. I never figured there’d be a chance for anything more than fantasizing about her. As I was packing all the equipment I needed for the live broadcast into the station van, I saw Tammy walking across the parking lot. She called out, “Hey Eddie…”
“What’s up?”
Tammy scrunched her face up a bit as she reached me and said, “David (her bf) isn’t going to come with me tonight. I want to be able to drink. Is it cool if I just ride with you?”
This wasn’t an unusual request. Other station employees regularly tagged along with me so they didn’t have to drive back after drinking, so I didn’t really think much about it. I told Tammy that was fine with me, but I needed to get rolling by 3:30 so I had time to get there, set up, and be ready to go live at 5:00pm.
She thanked me, said she had a change of clothes in her car, and would be ready shortly. I finished loading up the van and headed back into the station to talk to my board operator. When I returned to the van about 20 minutes later, Tammy was standing there waiting. She was wearing a pair of tight denim shorts, pink scoop neck t-shirt, and flip flops. We jumped into the van and headed for the interstate. I realized that while I’d talked and joked with Tammy at work and station events before, this was the first time I’d ever spent time with her alone. While I kept stealing glances at her long, taut, tanned legs as we drove, I kept the conversation appropriate. We talked about where we from originally, where we’d gone to school, how we ended up here, and gossiped a bit about coworkers. One interesting nugget Tammy shared was that she and David had been fighting a lot lately because he felt she partied too much, and was getting to an age where she needed to settle down some.
The Friday Afternoon Club went very well. It had become somewhat of a tradition for listeners to buy me shots of tequila at these events. Idk how that started, but it had become something I could count on. The place was packed and before I knew it, there were a dozen shot glasses on the table. I told Tammy, “if I’m gonna get the two of us back home in one piece at some point, you’re gonna have to help me out with this tequila!” Her face lit up and she scampered off towards the bar. She returned with a cup full of lime slices and said, “Let’s do this!” Over the next 3 hours, I drank 3 beers and downed 4 shots. I’m 6′ and 200 pounds, so if I pace myself, I can generally handle that amount in that time frame pretty well. I can’t tell you how many beers Tammy drank, but she downed the remaining shots and was having a grand time! We hung out until about 9 just to make sure I was in solid driving shape, loaded everything up and started back.
Tammy wasn’t “falling over” but she was clearly drunk. She thanked me for driving and told me what an awesome time she’d had. “You know, David always bitches at me when he comes these things. He always tells me I drink too much and talk to too many people. But I’m in sales, I gotta meet people! Right?!”
I laughed and agreed. I told her she was fine and just having fun. The conversation then took an abrupt and unexpected turn!
“Eddie, do you think I could be in Playboy?” I stuttered a bit, not sure what to say. The question came out of nowhere like a left hook. And she asked it so matter of factly.
“Where did that come from?” I asked.
“Okay, so I’ve been working out a lot over the past couple years and I told David I might wanna try to be in Playboy. He told me it was a stupid idea and that my boobs aren’t big enough anyway.”
I took a deep breath, gathered my wits, and replied, “if that’s something you’d like to do, you should go for it. You’re obviously a beautiful woman! As far as boobs go, seems to me yours are more than adequate. But there are plenty of girls in Playboy who don’t have huge boobs so I don’t know what that’s got to do with anything?”
Driving was a bit of a challenge at this point. I wasn’t exactly stone cold sober, and I was now hip deep in conversation with this beautiful girl about her desire to be in Playboy. I focused for a moment and then glanced at Tammy. It was dark but but I could see her smiling at my response. “I know, David is such a jerk sometimes. All he does is criticize.”
I decided to push a little further and see where it might lead. In my best joking tone, I offered, “however, I can’t truly offer an opinion on the worthiness of your boobs if I’ve never personally seen them.”
I didn’t expect the response I got. Tammy got very serious and said, “I’ll show you but you have to be honest. Tell me if I should consider having them enlarged or if you think they’re good enough.”
I held back a laugh (this was clearly a serious thing to her), nodded, and told her I would be 100% honest. We were still a good 20 minutes from getting back to the station, but I knew there was a rest area about 5 minutes ago. I told her I’d pull over there so I didn’t drive into the median when she flashed me. She spent the next few minutes explaining all the opportunities she felt would open up to her if she were chosen to model. By the time we reached the rest area, my cock was throbbing in my shorts. I pulled to an area furthest from the facilities, put the van in park, and turned to face Tammy.
“Alright, let’s see what you’re working with!” I couldn’t believe this gorgeous girl was excited to have me rate her rack. Tammy turned in her seat, reached under her t-shirt, undid her bra, and pulled her shirt up to her neck.
The definitely weren’t huge, but they were amazing! I’m no expert but probably a nice “C” cup, perfectly round, incredibly firm, and topped with medium sized brownish nipples.
I stared for about 15 seconds before she said, “Well?”
I cleared my throat, “Wow Tammy, those are awesome boobs. Seriously, those are probably the most perfect tits I’ve ever seen.”
She looked down at her chest and offered, “I know they’re nice, BUT sometimes I think they aren’t big enough for my body. I’m tall. Do you think they need to be bigger?”
I shook my head side to side, “no, I wouldn’t think about messing with anything that looks that great. Any guy would be jerking off to a picture of those boobies.” I couldn’t believe those words had just spilled out of my mouth. But the situation was so crazy to begin with. I quickly apologized, “I don’t know why I said that. I’m sorry, that was crude.”
Tammy was smiling, though. “Really, so you’d get horny looking at me?”
I was suddenly embarrassed. This woman, 10 years my junior, had me flustered. “Umm, I think you know you’re smoking hot.”
She was clearly pleased by all this and her demeanor changed from serious to playful. Still hold holding her shirt up, she looked directly into my eyes and whispered, “so, are you hard right now?”
I didn’t know exactly where this going, but I knew I wanted to play along. I nodded slowly and told her I was sure she knew exactly what she was doing to me. I could see that her nipples were now visibly stiffer and larger. She let her right hand drop to her breast. She cupped it and pinched her thumb and forefinger to her nipple. She rolled it slowly and asked if that made me any harder. I told her I couldn’t remember the last time I’d been this hard and she quickly replied, “and what does that look like? Maybe it’s time for you to show me something?”
I quickly scanned the rest area to make sure we were “alone.” A few cars parked near the facilities and a couple trucks at other far end. Returning my focus to her perfect breasts, I reached down and undid my shorts. I lifted my hips and slid them down to my ankles. The bulge in my boxer briefs was clearly noticeable. There was a small spot of precum that had leaked through.. Tammy pulled her t-shirt over her head and dropped it on the seat between us.
Squeezing both breasts now, she grinned, “the briefs too. I want a clear view of what I’m doing to you.” Hooking my thumbs into the waistband, I eased them over my stiff cock and down my legs.
“Nice,” whispered Tammy, “that’s all because of me? You said any guy would jerk off looking at me naked, right? Go ahead, I want to watch you do it while you’re looking at me.”
My head was spinning! I don’t know if it was just the tequila or if this was typical unbuttoned away-from-work Tammy, but she’d stumbled right into one of my biggest fetishes. I leaned back against the driver door to give her a full view of my twitching cock and said, “okay, I can do that BUT it’d be hotter if you undid your shorts and we watched one another.”
Tammy leaned towards me, and her tone became more serious. “I really like that idea but two things. This has to stay completely between us, and no touching one another. David is a jerk, but I still live with him. And you’re married. I’m so hot to do this right now but I have to be able to trust you.”
I just nodded. She smiled and undid her shorts. They were tight and she struggled to get them over her hips while in the van, but eventually slipped them completely off along with her panties. She lifted her left onto the seat and placed the right on the floor. The thin landing strip above her bare lips matched her sandy blonde hair. I don’t know if she ever achieved her dream, but I can assure you it was like having a playmate sitting naked and spread eagle across from me. Even in the faint light of the parking lot, I could see her glistening with wetness and the air was thick with her aroma. She squeezed her left nipple as her right hand glided down her stomach. I closed my right hand around my shaft and pumped twice as her middle finger eased into her wet pussy.
She whispered that she loved my cock. Not too big, not too small, beautiful head. I thanked her and told her again that I had imagined her naked many times but couldn’t have guessed how amazing she looked. I sheepishly offered, “I don’t have any lube or anything. I understand the no touching thing but maybe you could hook me up a little,” motioning towards her pussy with my left hand.
She paused a moment and said, “okay that’s fair.” She bunched her middle three fingers together and pushed them deep into herself. She worked them in and out several times and eased them out. She slowly reached over and spread her juices along my shaft. She then raised her hand and pushed those fingers into my mouth. “That’s all you get.”
Again my hand dropped to my dick, spread her wetness over the head, and began to slowly stroke. I could’ve easily cum immediately but I wanted to do anything to make this last. Her eyes were fixed on my slow strokes and I could hear how wet she was with each push of her fingers. Her left hand dropped from her nipple to find her clit. She now making small circles around it while keeping two fingers buried inside herself. I could tell by the way she was rocking that hand, she was working her G spot.
“I’m getting close,” she panted. “I might squirt. Cum with me!” I couldn’t speak. I picked up the pace and began allowing my thumb to work the head of throbbing cock. I watched as her hips raised off the seat and she let out a low groan. I fought to keep my eyes open as I felt my orgasm begin to overtake me. Her breathing shifted to short loud pants as the first rope of cum exploded from my cock. It landed on her leg and she immediately went off, screaming, “I’m cummmmmming, ohhhhh god.” I milked spurt after spurt of cum from my cock as I watched her writhe back and forth across the seat from me. I don’t know that I’d ever cum that much previously or since that time. Tammy’s head was now back on the passenger door armrest and her hands were on her stomach. Her breasts were heaving with her breathing. Her pretty little pussy was wide open and still pulsing. An absolutely gorgeous mess. I don’t think she actually squirted but it was still the hottest thing I’d ever seen.
We lay sprawled on the front seat for a few minutes. No words were exchanged. Finally, she sat up and said, “I needed that for a couple reasons. Thank you.”
I laughed playfully, “no, thank YOU! That was so fucking hot.” We found a stack of fast food napkins in the glove box, cleaned up a bit, pulled our clothes on, and started back out onto the road. As we drove back, the conversation turned back to the mundane. We arrived at the radio station and I asked if she was okay to drive the rest of the way home. She assured me felt great and jumped into her car to go home. I carried some equipment back inside and drove home.
The subject was never brought up again between us, and there no further encounters beyond daily work business. Tammy ended up leaving to take a job in another state about 8 months later and I never heard anything more from, or about her. But it’s still at the top of my spank bank to this day!
Source: reddit.com/r/eroticliterature/comments/qilcav/coworker_f_shows_me_m_how_she_does_it_on_the_ride