My Catholic Ex-Girlfriend’s Journey to the Poophole Loophole [MF] – Part 1

Spring of 2008.

Melissa and I met at Freshman orientation. We started dating in the second semester of my sophomore year—my first official college girlfriend. We had both just started dating. I got to our school on athletic scholarship (baseball), and she got in on her academic acumen.

The baseball season had just started, and Melissa was determined to make all my games, even though I told her she totally didn’t have to. I played center field, and I was pretty decent. But I really got a boost to my batting average when Melissa and I dated.

Melissa was very cute. She had a shoulder length brown hair, and stayed in great shape. She was about 5’2 and had a nice butt. Perhaps the best physical feature though were her impossibly large boobs. She’s had a reduction now, but man, they were huge.

Melissa was raised very conservative. Most religious girl I ever dated. She attended mass every week. She didn’t drink and she never used profanity. She had a few boyfriends in high school and one her Freshman year but, she—unlike me—had never done anything with them besides hold hands and kiss; she was a virgin. She wanted to save herself for marriage.

Dating Melissa was great—we got along really well, and I honestly was fine with no sex. I wasn’t really good at it (hopefully I’m better now) and I was happy just to be dating a beautiful, smart girl.

We were dating for about a month when we were making out between games in my dorm. We had a double header that day. I played like shit, we lost and I felt like I let my team down. I was trying to fix my mental, but it was difficult.

Melissa tried to comfort me, “I’m sorry about the game, but you’ll get them this afternoon!” She was so sweet.

“I just can’t fucking h-“

“Ryan!” She wasn’t used to me using that kind of language around her.

“Sorry, babe.” I apologized.

“Sorry, I just don’t know what it is lately. I’m playing terribly. I couldn’t hit the broad side of a barn!”

“Well, is there anything I can do to help?” Melissa asked innocently.

“Well—no, I can’t tell you.”

“Come on, honey, you know you can tell me anything.”

Oh, how I wanted that to be true. I crossed my fingers and hoped she wouldn’t break up with me when I told her what I thought I needed.

“Sex. I think need sex. I’m getting blue balls all day just thinking about you, and it’s hard to focus.”

Melissa just looked at me.

“I’m so sorry,” I backtracked. “I do not want you to do anything that would compromise your morals. Forget I said anything.”

“C-can’t you just, um, masturbate?” Melissa squeaked.

“I do! I just-I don’t know. It doesn’t do the trick.” I replied awkwardly. “I-I should go get ready for the game.”

“Wait, Ryan,” Melissa began. “I can’t have sex with you, I can’t. . . But, I think I’m willing to masturbate you, if you really think it will help?”

I was totally shocked. Not only was Melissa not breaking up with me, but she was offering me a handjob. And I almost said no, I really didn’t want her to feel pressured to do anything. Then I looked at her tits trying to break free from the prison that is her shirt, and my semi was a fully.

“Yeah, I think I’d really like that.” I said.

“Ok. Can you . . . Take it out?” Melissa asked.

I slid my pants and my underwear off, and Melissa saw my penis for the first time.

Thank God she didn’t laugh!

I think it was probably the first one she had ever seen. But she didn’t back away, she reached her hand out and gripped my penis and slowly started stroking it.

I was in heaven. Just probably not the one Melissa believes in. I loved the feeling of my innocent girlfriend’s soft hands moving up and down my pole.

It was pretty apparent that Melissa only had one goal in mind, to make me ejaculate. She would barely glance at it at first, then quickly look away and continue the movements. All the same to me though.

It takes me a little while with a handjob, as good as it felt, and I suggested that Melissa take off her too to help get me closer.

“I can’t do that, Ryan! Why do you want me to take my clothes off?” Melissa asked, incredulous.

“Please, your body is so attractive, babe. I want it to be the reason I cum.” I respond.

“You mean ejaculate?”

“Uh, yeah.”

Melissa stopped stroking me for a moment, and I thought I had screwed everything up again. Then she took her hand off and grabbed the bottom of her shirt and lifted it over her head, then took off her bra.

Huminah-huminah-huminah

I was only expecting her to take off her shirt at the most, not her bra too. Not only was it great to see boobs in real life again, but Melissa’s breasts were even more amazing than I had imagined.

I was rock hard as Melissa continued pumping her hand up and down on my shaft.

This continued for a whole, when I wanted to see if I could be a little cheeky.

“Can I touch them, babe?”

“Ryan! I really shouldn’t be letting you do this, but fine if you think it will help.” Melissa replied. Needing no further invitation, I reached out and grabbed Melissa’s breasts, there was much more than I could fit in my hand. Melissa let out an involuntary moan, which made me throb.

“Does it usually take this long?” Melissa asked, switching hands.

“Um, yeah, sorry. Do you want it to go faster?” I asked.

“Yes!”

“Well you could put it in your mouth . . .”

“Ew, Ryan! I’m already breaking like so many of my rules by doing this. No, anything else?” Melissa asked.

“How about in between your t-, in between your breasts?” I prayed out loud.

I could tell Melissa was thinking pretty hard about that. She could just say no, and I’m sure I would be able to finish–but what if she said yes?

“I mean, it’s almost the same thing that I’m doing right now anyway, right? Just use my breasts instead of my hand?” She inquired.

It’s happening, people!

Melissa went to her knees and, I gave her some lotion to help make them slick. “Just let me know when you’re going to, you know . . .” She commented, referring to me cumming.

All lotioned up, Melissa leaned forward, and took my dick between her breasts. I’m not too proud to say that it completely disappeared in there, there were so big. I directed her to stay still while a fucked her tits. My dick reappeared between those perfect pillows with every thrust upward, and drove me maddeningly close to my orgasm. It was quite literally a dream come true. Watching her squeeze her tits together while she watched me jump them, and I could tell she was finally getting into it. This was turning her on, hopefully as much as it was to me.

I was very close—just needed a little extra push. “Do you like having my dick between your tits, babe?”

“Ryan!”

“What,” I laughed, “talk dirty for me, it will make me ejaculate, I promise.” I hoped it would.

“Your big dick feels so good between my tits, baby.” Melissa moaned, her face was flushed with embarrassment.

Fuck, that did it.

Listening to my innocent girlfriend even say those words, pushed me past the point of no return.

“I’m going to—“ but I couldn’t say what because cum had already started shooting out of me. The first jet hit Melissa under the chin and slowly leaked down. Melissa let go of her breasts and took it in her hand mid spray, causing thick cream to land on her face.

“Oh!” She cried. She aimed the rest away from her, and I finished in her hand.

When I was done, Melissa looked at me, a thick string of cum hanging off of her chin and cheek, and said, “now go play some baseball!”

I hit a home run in my next at-bat.

Source: reddit.com/r/gonewildstories/comments/sv6l1q/my_catholic_exgirlfriends_journey_to_the_poophole