Giving [M]y [F]irst Blowjob: An Awkward Tinder Hookup

This is my first ever post on Reddit, and I am not proud of this story. However, it is completely true to the point that I hope the guy in question doesn’t find this post. Also it ended up being really long…please be nice!

Some back story: I’m a 23 year old bisexual girl. I first had sex with a girl when I was 16 and have had a few serious relationships with women, but my experience with men was limited to some high school kisses. Recently I found myself growing curious about cock. To the story…

For the past year I have had a casual FWB relationship with one of my close female friends, I’ll call her Alison. Alison is 29 and bisexual, and has a lot of sexual experience after being quite promiscuous in her younger years. One night I admitted to Alison that I feel a bit pathetic having not done anything sexual with men in my life.

I expected Alison to reassure me that there is no reason to feel insecure, but instead she encouraged me to find a man to sleep with. We settled on me giving a blowjob because that was more within my comfort level. Alison asked me if I knew much about penises, and when I told her I didn’t she gave me some tips. She described techniques like how she likes to lick the length of the shaft like an ice cream, and then pop the head in her mouth. We watched a few blowjob videos, and I was feeling really turned on. Alison and I ended up having passionate and sweaty sex that night, but that is another story.

The fact of the matter was that Alison convinced me that I would like the experience of giving head. And seeing as I really liked Alison, I wanted to impress her. The next day I created an account on Tinder. Now I am not a model, unlike Alison who is drop dead gorgeous. I’m chubby, but I have a pretty face with blue green eyes, nice lips, and long naturally golden blonde hair. My Tinder bio consisted of some lame comment about my job and how I love dogs. I chose tame photos that didn’t even show off my cleavage. Being from a small city I knew I would run into people I knew on the app.

I was selective with my swipes, but gathered around 50 matches by the next day. Tinder is easy when you’re a girl. I waited for men to talk to me first, created some smalltalk, and segued into asking the men what they were looking for. I don’t think a single guy admitted that they wanted a hookup, but I was straightforward in my response. I explained that I was bisexual and inexperienced with men, but was eager to give a no strings attached blowjob (no more, no less). As you can imagine I had a line up of men, all of which I found attractive, who would willingly oblige.

I excitedly called Alison and told her about how I downloaded Tinder and had a number of potential guys. Alison came over and looked through the messages and profiles with me and we narrowed the choices down to three guys and I exchanged numbers with them. I sexted a bit with each of the guys and got them to show me their cocks. Thankfully they all looked nice, and I decided I would meet up with whoever could get together quickest before I lost my nerve. This lead to me choosing a 23 year old baseball player named Ryan. Ryan had dark brownish-red hair, a nice body, and decent sized cock. It looked smooth, thick, and long enough to work with my hand while I sucked it (something I wanted to try).

In the days leading up to our meeting I added Ryan on Snapchat and showed him my boobs and my pussy. He sent me videos of himself jerking off telling me how he thinks my little pussy looks perfect for his cock. Ryan was really turning me on. I showed his cock to Alison and she told me it looked perfect to practice on.

We decided a day to meet where he would be home alone. Ryan lived in a bigger city nearby, which also happened to be where my job is. Unfortunately I ended up having to work late that day and Ryan would no longer be alone. At this point I decided to forget the whole idea and even texted Alison to tell her I changed my mind. But then Ryan started to send me videos of him jerking off and made me horny at work. He managed to convince me to pick him up when I finished work to give him a quick blowjob before I drive home. I was incredibly nervous, but decided it was now or never.

Ryan told me where to pick him up and I was on my way. To set the scene this was in January and I live in Canada. The roads were covered in deep snow, I was wearing a winter jacket, and Ryan was waiting outside. Of course being unfamiliar with the city I ended up in the wrong place. After an extra 5 minutes or so I find Ryan standing at the side of the road where he said he would be. I pull over and he gets in my car.

I said hello to Ryan (in a weird fake sexy voice that I didn’t know I had) and asked him where he wanted to go. When he told me to drive straight down the road I noticed that Ryan had braces. I thought ok…so his profile definitely didn’t indicate that he has adult braces but he seems nervous and not like a serial killer so I guess that’s a bonus. We drove down the road and he eventually tells me to slow down in front of a park. However, the parking lot was not plowed and there was no way in hell I was getting my rear-wheel drive Ford Focus into that lot without getting stuck. Ryan tells me that was his only idea of were to do this, and I can feel the knots growing in my stomach.

Ryan and I continue to drive aimlessly down roads covered in thick slush and snow looking for a place to pull over. My car was sliding. I considered telling him to forget the whole thing but then we saw a parking lot behind a convenience store that was plowed and I pulled in. There were a couple other cars in the lot but they were snow covered and looked like they belonged to staff. I turned to Ryan and asked him if he wanted to make out, and he said he did. I leaned over the console and see Ryan coming toward me with an open mouth. I braced for impact (no pun intended…adult braces remember) and he shoved his tongue in my mouth. We made out for about 30 seconds, and it was much more aggressive than what I like. I literally struggled to find his lips. Thankfully his braces didn’t seem to make a difference, maybe because his mouth was open so wide.

While we were kissing I put my hand on Ryan’s crotch. He was wearing sweatpants and I could easily feel the outline of his cock. When I broke away from the kiss I glanced down and told Ryan to pull his pants off. He quickly pulled down his sweat pants to around his knees, and was sporting a partial erection. Ryan proceeded to ask me how to recline the front seat, and asked if I could turn the lights in the car off (DOH! I was so nervous I didn’t even notice we were in a brightly lit car). In order to make the lights turn off I had to turn off my car which made me nervous seeing as it was winter in Canada.

After what felt like a hundred years the seat was back, the lights were off, and I was face to face with my first cock. It looked bigger in person. I leaned down and licked along his shaft like Alison suggested. I got my hand wet with saliva and started stroking his dick while I watched it grow into a full erection. I told Ryan it looked nice, which caused him to groan happily. I was surprised his cock felt so soft to the touch despite being rock hard but somehow it did.

I leaned back down, balancing with my ass off the seat and my leg pushing on the inside of the door, and started licking his shaft some more. After a few moments I decided I was ready to pop his head into my mouth. Ryan grabbed my long hair, which kept getting in the way (note to self: always bring a hair elastic when sucking dick!) while I experimented with running my tongue over his head. I took his cock a bit deeper while gripping the shaft in my hand, and attempted to swirl my tongue around the ridge of his cock, which was harder and less smooth than it looked in porn. I started to pump his shaft in my hand and bob my head up and down while creating suction with my mouth. Ryan nicely told me “less teeth.” I thought to myself FUCK HOW COULD I FORGET TO PAY ATTENTION TO MY TEETH! But tried not to be discouraged.

I continued to suck and stroke his cock, trying my best to create a rhythm. It took a while for me to discover what to do with my tongue while his cock was in my mouth but after a while I felt like I was getting the hang of it. I settled on licking the underside of his head with a flat tongue while I sucked. Ryan wasn’t giving me much feedback, and I asked him for tips. He told me to “take the whole thing” and proceeded to push my head down on his crotch, deep throating me. I had told Ryan when we sexted that I had a strong gag reflex, and he got to learn why I had told him about it. After a few seconds I gagged on his dick and had to come up for air. I told him sorry, but I can’t do that.

I managed to get back into the blowjob, and Ryan reached over and started rubbing my ass through my leggings. I felt my pussy getting wet and just kept thinking “I can’t believe I’m sucking a dick right now.” However the moment was ruined when Ryan tried deep throating me. Again. And I gagged all over his cock. Again. He told me it feels better the deeper I take it, and I warned him that I don’t want to puke in his lap so he better stop trying to deep throat me if he wants to cum. He eased off, but continued to push my head down while I sucked him. I decided that as long as he didn’t push my head hard I could deal with it.

Ryan asked me to stroke his cock with my hand while I just lick the tip. I thought to myself great, I am so bad at blowjobs that he just wants a handjob + some tongue action. I started to jerk him off moderately fast, with a tight grip on his shaft, while licking the head of his dick like Ryan requested. I felt like this blowjob was lasting forever and I decided to pick up the pace. I stroked his cock with fury, spitting on the shaft to keep it lubricated, and maintained a rhythm with my tongue. I noticed that Ryan was starting to lift his hips off the seat to meet my mouth so maybe (hopefully!) he was close. I popped his head back inside my mouth while still jerking his cock, working my tongue the best I could while creating suction.

After a short amount of time I started tasting something bitter, and kind of gross, in my mouth. “So that’s what cum tastes like, no wonder so many women spit.” His cum was pouring out of my mouth onto his dick and lap while I continued stroking him, to make sure he was done. I pulled away from him and asked him if he wanted me to stop, to which he replied “Well I came so…” I opened the console and passed him a napkin to clean himself up and turned the car back on.

My windows were completely fogged up and I didn’t wait nearly long enough before driving away. I was lucky not to smash the back of the convenience store, seeing as my back window was complete opaque. Ryan directed me toward where I had picked him up and told me which way to go to head home. I awkwardly apologized to Ryan about making mistakes, because I had never touched a penis before. He told me it was alright and we said our goodbyes.

I started feeling anxious and insecure about what I had done on my way home. I had never hooked up with anyone and the way it happened was sketchy. Plus, I felt like I had done a bad job. As soon as I got home I blocked Ryan and deleted him off Snapchat because I decided I wanted to forget it happened.

Alison was proud when I told her I had gone through with it, and told me she would make up for his lack of reciprocation.

I do feel regret about hooking up with Ryan, but I am glad I got my curiosity out of my system.

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TLDR: My FWB convinced me to find a guy on Tinder to give a blowjob. I ended up almost getting my car stuck in the snow and gave a mediocre blowjob to a guy while parked behind a convenience store. Cum tastes bad.

Source: reddit.com/r/gonewildstories/comments/6ew56h/giving_my_first_blowjob_an_awkward_tinder_hookup