My Catholic Ex-Girlfriend’s Journey to the Poophole Loophole – The Final Chapter [MF]

Thanks for sticking with me everyone. This has been fun to write for you all—and I’m glad that so many people liked it. Alas, this is the final saga of my Catholic ex-girlfriend’s journey to the poophole loophole.

A month or so went by and we were in the conference playoffs. Up to then, Melissa and I had become quite proficient at giving head to each other. I could make her cum multiple times with my tongue (call me, ladies), and she had learned a few tricks too.

We got together one night to hang out and watch some TV. I knew how to pirate TV shows and airplay it through my computer to the TV and this was right during the height of How I Met Your Mother. Melissa and I loved watching it together.

My roommate and best friend (Eric) was cool and always gave us the room together for a few hours. But when Melissa took off her jacket, I knew that tonight was going to be different. We usually watched it in our pajamas, had a little fun, then sent her home for the night. Melissa also usually just wore some regular loose fitting pajama pants and a t shirt. Nothing firm fitting—prime comfort level. But not that night.

My gorgeous ex was wearing the least conservative set of pajamas I had ever seen. It was a long sleeve close fitting short romper that showed off Melissa’s irresistible curves perfectly. It was great with red trimming and a deep V neck and they snapped at the bottom between her legs.

Just seeing her like that made my schlong visibly strain against my pants, and she knew it.

Soon I had the show going, and Melissa was much more into it then me, mostly because I was staring down the unbelievable cleavage that her outfit had created. I stayed erect through the entire first episode.

Then a scene came on and people were kissing and Melissa turned her head to face me. There was lust in her eyes. In that moment I knew I would have her. I leaned in and started kissing my tease of a girlfriend deeply.

As we kissed, I began sliding my hands over Melissa’s breasts, then pulled at the center of her outfit until it snapped open and her huge, beautiful tits spilled out. I gently squeezed one of her breasts, then the other while we made out.

Soon, I was laying on top of her, and began to press my sheathed cock against her mound. I almost thought she would stop me, we had never dry humped before, but her moans spurred me on.

I began to thrust against my girlfriend’s virgin pussy through our clothes. I, for one, was thrilled that my previously conservative girlfriend was letting my dry hump her, and apparently enjoying it.

I did something I shouldn’t have, guys. But I was caught up in the moment. While we kissed, I took off my pants. Her outfit was so tight that I could now feel her privates against mine much easier.

Then I did it again. I took off my briefs, and my cock sprung free like a caged animal. It felt so good. And so forbidden. As I resumed thrusting against her outfit, I could feel that Melissa was wet, as it was seeping through her material.

I didn’t dare, take off Melissa’s outfit. That would be entirely her decision. With each thrust, my cock slid against the soft fabric covering my girlfriends pussy.

Then the unexpected. Melissa started cumming. She moaned into my ear, “oh my God, I love this!”

As she finished and in mid thrust against her groin, Melissa told me to stop, and I did.

“Ryan, I have this girlfriend. She’s from my church. Anyway, a couple weeks ago, I confided her the kind of things we were doing. I probably should have told the priest, but I was too afraid.”

“Anyway, she um, told me about a way we could be more . . . intimate, without losing my virginity . . .”

You guys know where this is going. But to 19 year old me, I hadn’t ever seriously thought about anal sex, and I’ve never really been a porn guy, so I hadn’t seen or heard much about it.

I sat dumbly quiet, waiting for Melissa to expound.

“Well, she and her boyfriend also wanted to have sex but she wanted to stay a virgin. So they came up with a solution to their problem.”

“So how did they have sex without . . . having sex?” I’m an idiot, guys.

“They had . . . anal sex.”

Now my brain had caught up with the conversation.

“So just so we’re clear, you are saying you want to try anal sex?” I asked, surprised.

Melissa’s eyes met mine, and I could tell with some difficulty she admitted that she had researched it online. That she had tried putting things in, small things with lots of lube, and that it actually felt pretty good, to the point even where she thought she was read to try it with my cock.

I was shocked.

Now, guys. At the time, I would much rather have stuck my penis in Melissa’s pussy, but I thought that this might be the closest I would ever get (especially if she decided she didn’t like it after) so there was no way I was passing it up.

I told her I wanted to do it too. With that, Melissa unsnapped the bottoms of her outfit, exposing her pussy and her tight ass to me. She has brought KY Jelly I’m her purse. It clearly wasn’t a full tube, which made my penis stand a little bit taller.

Melissa was clearly nervous, I was clearly nervous, but our lust for one another won out. She poured a generous amount of lubrication into her hand and started stroking my cock, getting it very slick, and I remained rock hard.

Then my beautiful, sexy, innocent Catholic girlfriend turned around, and got on her hands and knees on my bed, presenting her ass to me. She looked at me, “please go slow, “you’re bigger than anything I tried before.”

Sidebar: I feel impressed once again to remind you all that I do not have a ginormous dick. It’s completely average. So I was not about to ruin this poor girl’s asshole by any means.

I spread Melissa’s cheeks and lined my wet dick up with her asshole for the very first time and began to slowly push forward.

The lube was worked, as little by little I slid until I was a few inches inside my girlfriend’s ass. Melissa grunted in pain as I held myself still inside of her.

I felt her relax and slid another inch in. Another whimper of pain.

“Babe, are you sure about this? I don’t want to hurt you.” I really didn’t, but my mind begged for her to tell me to keep going, because her ass had instantly made me love anal.

“Keep going,” she said through gritted teeth before relaxing again 4 inches inside of her.

I pushed in one more inch, until Melissa tensed up again. She relaxed again and I pushed in with my final inch.

“Sweet mother of Mary,” I thought. That was probably akin to blasphemy in Melissa’s religion. I absolutely loved how tight she felt around me. I loved mounting my girlfriend from behind and watching her be so submissive for me.

I gently pulled out until only the head of my cock remained inside of her, and slowly descended into her depths once more. My whimpers of pain this time. I pulled out almost all the way again and just as I went to push back in, Melissa spoke.

“Ah, I’m getting used to it, you, ah, can go in a little, ah faster, if you want.”

Perfect.

I pushed in a little faster, this time met by a moan of pleasure. “Oooohh, faster, baby.”

Out again, and in again, even faster.

With each thrust she told me to increase my pace.

There were no more stops between thrusts. I could feel my balls slapping between Melissa’s legs, and her tits were visibly swinging wildly.

She was really getting into it.

“Pound my ass, baby!” She called. I could hear her smiling as I held her hips and thrust.

That was it—the point of no return. But I still had the common decency to ask where she wanted me to cum.

“Inside! Cum inside my ass, Ryan!”

I felt the familiar boiling in my balls, bottomed out against my virgin girlfriend’s ass, and launched my batter inside of her with a loud (very manly 😜) groan.

I slowly pulled out of my girlfriend. She collapsed onto her stomach, and I watched as a pool of cum leaked out of her.

I looked at the clock. Shit, Eric would probably be back soon.

Melissa told me the next day how bad her butt hurt when she woke up. Thinking back on it now, I feel bad, because with the experience I have now, I would have got her waaaay more ready before just sticking it in. Melissa said she had to stay home from school just so she wouldn’t have to sit in a hard chair. Still, she enjoyed it, and we made it a semi regular part our routine (she even started to cum during it) until we broke up.

It was sudden. She called me over the phone when I was visiting home for the summer and broke up with me. I was devastated, but I still had plenty of fun after her and I were through.

Melissa is married now (I’m not). She’s got three kids and a husband. I obviously never got to have her in every way, but I wonder if she ever told him about her first time for everything else.

Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/t1fi7s/my_catholic_exgirlfriends_journey_to_the_poophole