u/Chasinthatfeeling

This is the story of our first time. I tried to make it as detailed as possible yet still being engaging as a story. I hope you enjoy!

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The first girl I ever dated is my current long term partner. We met almost 13 years ago in college and started dating a month after we were introduced.

Prior to this relationship I had very little sexual experience. We both come from more conservative religious backgrounds where sex before marriage was taboo. I'd made out with a girl in high school a few times, but felt guilty about it and broke things off. That was the extent of my experience. My girlfriend had dated a couple people back then but only fooled around with one of them. They never "went all the way" but came close. Relative to me she came into our relationship with way more experience - though that’s clearly not saying too much!

We started having sex a few months in. It was a learning experience for both of us. There were many contraceptive mishaps and plan B‘s in those early days. Despite our inexperience and the latent shame that premarital sex carried with it, we were still having a good time. It was particularly exciting for me because by 22 I was quite honestly desperate for a romance. Our relationship was a dream come true, made even better by the fact that I was so attracted to her. She had a similar body to the women in porn I gravitated towards. Brunette, pale skin, large F cup tits, thin waist and wide hips. She was and still is absolutely stunning.

I was finally having sex - and with the girl of my dreams no less. Once I'd finally acclimated enough to not bust after ten seconds, we began to find a rhythm. With that rhythm came experimentation and dirty talk. At first I was nervous and unsure what to say, but the desire to turn her on overrode my apprehension. In my first attempts I simply parroted what I'd heard in porn. Inevitably, a certain phrase I had considered to be completely innocuous escaped my lips as I took her from behind, it being: "yeah, take that big dick!"

Now, I’d never really thought about the size of my dick before because when you come from a background like mine its not just the act of sex that's taboo, but any discussion of it too. I actively avoided participating in "guy talk" (as it were) for basically my entire young adulthood. I never compared my thing with friend's things, and to be quite honest I never really paid that much attention to the size of male porn stars. Consequently, I was completely unaware that I was actually quite small. I'm five inches long on a good day, and not gifted in girth either.

What I also didn't know is that my girlfriends high school squeeze had the opposite problem. And while she'd never taken it inside her she was nevertheless intimately familiar with big dick. As soon as I spoke the words she turned, cocked an eyebrow and very kindly questioned why I would say that. Our post-session chat that afternoon put me in my place, including a non-judgemental comparison of his and mine, plus an admission from her that she’d immediately noticed my lack of size. The thought had crossed her mind the first time she went down on me.

Though she insisted size didn't matter to her, in the moment this insistence took on a nervous tone of reassurance which made me question things. It wouldn’t be until much later when she'd finally admit to me that for the first few years of our relationship my poor technique paired with my lacking size often resulted in underwhelming sex. As I made love to her, she often found herself wishing for more foreplay. But I'm getting ahead of myself.

For the next couple years we continued to experiment. Our apprehensions towards the taboo began to wear away along with the shame and inexperience. It was during this time that I began seeking out more diverse kinds of porn and discovered the cuckold/hotwife genre. It was also around this time that she and I began discussing how our hyper-conservative upbringing had stunted our sexual development. In short: neither of us had ever been able to sleep around or try new things. We both secretly craved a "hoe phase" and had danced around the issue for a while.

Shortly after moving into our first apartment, we decided to open up our relationship. The timing made sense. We finally had the space and privacy to safely let loose our pent up energy, and out with that rush of energy came our suppressed desires. We both installed dating apps. We shared the crushes we'd been nursing on celebrities, co-workers and friends. We role-played. We called each other by their names between the sheets.

But since that embarrassing moment in her dorm room years prior my insecurities around my size and performance had only grown. She had yet to be critical of my shortcomings, but had begun to occassionally indulge my ever-present humiliation kink. I desperately wanted more. I wanted her to put me down and mean it. I wanted to her to sleep with a bigger, more experienced man and return home to tell the tale. I sheepishly pestered her for details about her high school escapades. How she struggled to take him down her throat. How he thrust himself between her tits and came on her chest. How he laid her back under the stars on a cold autumn night and fingered her until her shivers turned to quivers and sweat. For months I obnoxiously treated her like a broken record, and she graciously obliged without skipping a beat, until one day [vinyl scratch] she met someone.

The man in question was a regular at the cafe where she worked. He'd take lunches there on break from his job at an upscale plant shop in the small urban campus their businesses shared. One day after a particularly flirty exchange she slipped him her number. He texted back soon after.

When she showed me his Instagram I understood her attraction immediately. He was very handsome and quite well built. Average height, broad shoulders with big arms and thick thighs. One pic of him in a tank top and shorts showed off the extent of his tattoo coverage, along with his fur coverage. He was a hairy, stocky man with soft brown eyes, and supple lips that broke into a crooked smile. In other words- exactly her type. Thus far he’d been very kind and charming each visit since their initial meeting. All the flags were green. I hoped that would remain the case when she visited his apartment the following week.

The knot in my stomach grew as the date approached. The emotional whiplash between excitement and the fear was almost too much to bear. The fear however, was not borne out of jealousy, but concern. I was worried something bad might happen. What made it worse was that I worked a closing the same night they’d scheduled their rendezvous, which meant I wouldn't be able to communicate easily with her.

The last half of my shift that night was agony. I couldn't relieve myself from the pent up arousal, and on top of that I’d been so distracted that I’d forgotten to ask her for his address. I spent five hours completely in the dark on where my girlfriend was knowing that I’d be completely unable to find her if there was an emergency. Even so, through the worry I couldn’t help but imagine her naked in a strangers bed having an amazing time. All night two opposite sides of my brain were lit up at once and in a tug of war with each other. By the time I clocked out I was mentally exhausted.

On the ride home the insane irony of my situation hit me. Not three years before and I would have treated this not merely as taboo, but as a deeply depraved sin. If any of my friends or family knew where I'd willingly let my girlfriend go that night they would have looked at me like I'd been given over to a demon. To be honest a small part of me probably wondered the same. Upon arriving home I felt possessed by the temptation to relieve my pent up frustration. The ping of a long awaited text message notification is the only thing that saved me from impending post-nut clarity.

“Headed home. It went good, I had fun!”

Fifteen minutes later and she was walking in the door with a sheepish grin on her face. We hugged and I kissed her cheek. She set her bag down, took off her coat, used the bathroom, drank some water and I waited patiently on the bed, hollering a few boiler plate questions into the kitchen:

"So it went well?"
"Yeah, it was a good time."
"He was nice? He treated you OK?"
"Mmhmm. He was super chill. "
"Do you have the energy to tell me-"
"Yes, just gimme a sec."

It felt like an hour waiting for her there on the bed. When she finally snuggled up close and looked me in the eyes I was nearly out my mind. With all the brainpower she had left to muster she detailed for me the events of the hours prior. Her account went roughly as follows…

"I got ready here. Had a drink before I left cause I was nervous, and got a ride over. He opened the door for me and we went inside. We had a drink together and talked for twenty minutes or so. I put my legs out across his lap as we sat there (she was wearing a short skirt) and he rubbed my thighs."

I asked her how it began:

"He asked if he could kiss me and I nodded. He turned the lights low in his room and I leaned in. His lips were so nice. They're big and soft, and he was a good kisser. I started biting his lower lip and he told me it was turning him on so I took off my shirt and straddled him and he took off my bra. He told me how long he'd been wishing he could see my tits and I pushed them into his face. He was sucking on them for a while and I could feel his cock getting hard through his shorts."

Of course then I asked her about his dick, and how we compare:

"When I took it out I was surprised and pretty turned on. It made me a little nervous. Yeah, he's bigger than you. Yeah, baby, quite a bit. Not that much longer I think, but way thicker than you.”

She detailed for me how she sucked it as he felt her up. How it was tough to take all the way. How he moaned as she took it. She told me how good his fingers felt as they slid inside her. How they were soon completely naked and lying down on his bed under gentle lavender hue LED fairy lights…

"So then he got a condom from his nightstand and I spread my legs for him. He put it on and crawled up in between and I reached down and helped guide him into me. He pressed his head against my pussy and then slowly inside and started fucking me. I slid my hands up onto his biceps and squeezed them while he did it. It was so hot."

I kissed her intermittently as she admitted all of this to me. I moaned at every dirty detail and watched her eyes dart shamefully away even as she spoke with a tiny smirk pulling at the corners of her lips. I could tell all that sustained this ongoing confessional was the constant reassurance of my approval. I think it was my embarrassingly obvious enjoyment of the facts that gave her courage to utter the following sentence as her eyes rolled back and the smirk broke into a smile...

"How did it feel?" I asked.
She groaned, “I just didn't know a dick could feel like that.”

I couldn't believe it. Her tone conveyed a clear message, and the words I’d been dying to hear had been all but plainly spoken, so I asked for it bluntly: "did he feel better than me?"

Without hesitation, as if anticipating the question, she shook her head and said, "no, I mean it was just different."

Her face was red with embarassment. Still, I tried again:

"Did he make you cum?"
"Yes."
"How did it feel?"
"Really really good."
"Better than with me?"
"No, I told you, just different."

She was lying and it was obvious. I felt my face flush and a chill run down my spine. Instinctively my hand begin to drift down across my body and over her tummy, then down between her legs. She let out a little breath as I began fingering her and asking her to keep sharing…

"So, I got on all fours for him on the edge of the bed and he pushed his dick in. He pulled my hair and fucked me so hard. It felt amazing and I was screaming so loud so he pushed my head down into his pillows and I screamed into them. His housemates probably thought I was insane."

I asked her what her favorite position had been:

"My favorite was he pulled me close to him and rolled me on my side, and then pressed my legs together so he fit tight and fucked me like that. That felt the best by far."

"Like this?" I asked, as I tried to act out the position on her. We attempted it briefly but it became clear to me that I wasn't built for it, and plus I was hungry for more details and not a detour…

"Then he spooned me and kept fucking me from behind as he kissed my neck and squeezed my tits. He really likes my tits. He kept complimenting them over and over."

At this point she and I were an entangled sweaty, sticky mess and I just couldn't resist the urge to fuck her. I put her on all fours at the edge of the bed, just like he had a few hours earlier and fucked her slow, trying desperately not to cum as she related to me how they’d finished things.

"He made me cum really hard, and then I asked him how he wanted to cum. He asked if I could suck him off while I played with my tits in front of him. I got on my knees at the edge of his bed, sucked his dick and jerked him off until he grabbed his dick and came and came all over my chest.”

I felt like all the breath had let out of my lungs, but still somehow managed to beg for her to call me by his name. As she did so, I focused on one singular thought: my gorgeous girlfriend face down in his bed, his thick cock sliding in and of her, a pillow muffling her pleasured screams. The idea of her realizing just how “different” he felt, and the humiliating thought that as I fucked her, those “differences” were being made all the more obvious. I tried one final time to get the truth out of her…

"Be honest baby, he felt better than me? A lot better, right?"
"He felt really really good."
"Better, right?."
"I didn't say that..."
“I know you’re lying.”

I laughed as I said it. She just moaned and said, “I’m serious.”

I let the point go. Though I knew she was keeping her real feelings a secret, I didn’t want to push it too far. I wanted to end the night on a positive note. So I asked one final question…

"What was your favorite thing about him, baby?"
She answered slowly, breathless. The words came heavy and true.

"He just fucking pounded me, baby. He pounded me so hard."

I barely pulled out in time. Came all over her ass and got some on the sheets. We laid down and snuggled. We got up and took a shower. We collapsed in bed and knocked out. The next morning I woke up first and looked over at her, and realized our relationship was different now. I hoped we hadn’t opened a can of worms. I wanted things to keep being as great as they had been the night before. I wanted her to sleep with him again, but this time in \*our\* bed.

And she did. But that’s another story :)