TIFU by trying to have sex with a virgin.

Submitted by Tekripsz t3_xyzx7y in tifu

This happened yesterday and I’m still reeling from it lol.

So I’m not the most experienced myself either so I’m not big on judgement in that area. I met this boy earlier this week and went out on a date, then a day later he asked if I wanted to come over to his house while we were on the phone.

Cue yesterday where he picked me up and brought me over. His house is nice, his room was very much in the farthest back of the downstairs you could go. (Not the best cleaned either) We placed a few bets on each other the night before which led to us walking around naked pretty much most of the morning. One of the bets he lost was a bit odd and def more of a turn on for him. He wanted to be tied to a chair and have a shake funneled down his throat. I did it, albeit a bit uncomfortable myself since it’s not my sauce.

We then did some naked cuddling which turned into me getting him off and him trying to get me off. I’m fat so I’ve got a lot more cushion for the pushing, and he had a bit of a hard time finding anything down there. First he was just rubbing the outside skin area, and once he realized there was more then went in to rubbing more of the side of my vagina. I started adjusting and tried moving his hand so he knew where to go and things were dandy for a while. Then he went in harder than I liked, and along with that came his fingernails which was painful. Told him to stop and he did.

We made lunch and watched some movies/YouTube for a good while before he was ready for round 2.

Round 2 started with him asking me to be more of a domme mistress, which I am very much a submissive person so this was new to me. I tie him back up to the chair and do some dirty talk (very badly from my end ngl lol) I move him over to the couch and hand him a condom, he doesn’t know how to put it on so I had to help a bit in that department. After he tells me this would be his first time, not a big deal as long as he’s fully consenting with the situation.

He wants me to lead a bit and be on top. I’m only scared for two reasons, one I am sooo much bigger than him and two is that I’ve personally never been on top. I get on top and slip it in, it was fine for a few seconds until he kept slipping out every time I put it back in. So we decide to switch over to missionary. He put it in too high, then a bit low and finally had gotten the placement right, and had trouble thrusting, then lost his boner and apologized. He tried getting me off solo but ended up hurting me so I tried to get him to stop. I think he thought my sounds were more pleasure than pain, but it was painful.

I tried to make sure he didn’t feel too bad about his first time, could just be performance anxiety. He took me home pretty much after that. Tbh I had all of my friends saying I shouldn’t have seen him after the first date so it’s on me.

TL;DR. He had trouble with women’s anatomy and finding the right hole. I ended up sore and hurt in the end.

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Comments

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happie-jappie t1_irjq624 wrote

>He put it in too high

Ummmmmm. .. "I don't want that shit in my belly button, that's kind of like intercourse"

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Tekripsz OP t1_irk28w8 wrote

Funny enough I have a story of a guy who tried intentionally sticking it in my belly button 😔

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Fun-Pea-880 t1_irlsyo1 wrote

I had a friend who lost her virginity to her boyfriend, who was experienced and ended up cuming all over her inner thigh because he could never get it in.

Even with the lights off I don't understand how he could be that bad with his aim :(

Yes, she had bruises all over her inner thighs from all the different places he was trying to shove it into.

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Tekripsz OP t1_irm7ljo wrote

Awe nooo :( Poor girl, it’s insane how far off people can be with it 😭

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happie-jappie t1_irksn0m wrote

I mean, you can't drop that kind of teaser and then not tell the story!!

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Tekripsz OP t1_irktqd7 wrote

Okay you’ve cracked me 😂 I have some other gems from that same interaction.

I was trying hookups and met up with this guy in a hotel. He made it pretty clear beforehand that he was a big fat fetish person along with being a feeder. He bought us pizza and fed it to me, when I would get sauce on my face (I’m a messy eater lmao) he took away my napkins and sucked the sauce from/around my lips 😭😭 Along with that we started getting spicy and learned neither of us brought a condom. So we did some non penetration stuff but along with that he tried fucking my rolls and then my belly button. He also had the same issue of fingernails when trying to get me off 😬

All night earlier too he would stick his fingers in it and spat in it once. When I went home the next morning it was fully red raw and hurt to bend my torso because of how much he handled it lol.

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happie-jappie t1_irl89rh wrote

You need put in your whatever profiles that you require your partners to well manicured nails lol. So, based on this information of him trying to fuck your belly button - I'm going to presume he wasn't the most well endowed partner? gif

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Tekripsz OP t1_irlejf9 wrote

A quick nail check before we go in anymore. Haha also I’ll just say it was just enough to work with.

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A-Dolahans-hat t1_irkf7be wrote

Sometimes we just like to put it in weird places just for the hell of it or to be funny

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mapkhung t1_irne4ri wrote

Yea I fully agree. For the lolz especially. My wife is a nail and lash tech and she has this short stool with wheels, and she will just sit on it and roll around the room to get things done without standing up. Usually after I shower I just whip my dick on the back of her head, poke her ear, stab her neck, I mean, you get the gist 😂

Not sure if it’s just me tho. But I find it pretty fun. And she gets annoyed every time haha

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A-Dolahans-hat t1_irntqa3 wrote

Yep, this sounds right. We don’t expect anything to happen, but it amuses us greatly.

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happie-jappie t1_irp9wkt wrote

I believe it's one of the unwritten rules of have a pp, one must both use it to annoy our significant other as well as try to stick into as many different things as possible, for the lulz

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Tekripsz OP t1_irkm34b wrote

Interesting. Gonna keep that piece of info in my pocket lol

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Husband-fist-wife t1_irn9092 wrote

This is true. I can think of a few places I have tried to put it just for laughs. Sometimes it actually ends up feeling good too 😄

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PinkDancingFlamingo t1_irjj8su wrote

Sounds fairly typical for virgin sex actually lol. It gets better i promise

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Tekripsz OP t1_irjkugf wrote

For sure. Unfortunately with him I’m planning to end things. I found out today we’re very much on different sides of the political spectrum. I’d hope he could tell I’m much more leftist from my colored hair but 😅

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because_of_ghosts t1_irjmed2 wrote

Sounds like he didn’t make a judgement based on appearance, and neither of you knew each other as well as you should have.

That being said, it’s really nice to see an actual fuck up here, something that’s actually worth reading. Thanks for sharing and better luck with the next beau!

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Tekripsz OP t1_irjmtw3 wrote

For sure! Def should’ve spent more time getting to know each other before throwing ourselves at each other like that. Glad I could give a good read hahah

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Ainar86 t1_irzycln wrote

Well that much was obvious from the things he had you do, I bet if the relationship had progressed he'd have you strapping on XD

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[deleted] t1_irm76zt wrote

[removed]

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Tekripsz OP t1_irm7j4r wrote

Great comment bigtechbad. I’m sure this will affect me in many ways.

I know how bad that is compared to the furry, vore loving, feedism, water inflation, blueberry loving republican this guy was.

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SEND_NUDEZ_PLZZ t1_irkqvm8 wrote

Literally the only thing I did right my first time was cutting my fingernails beforehand in order to not hurt her lol

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Theolon t1_irmrwc2 wrote

If you think you're going to score, trim your fucking fingernails! And sadly some of you need to be told yo clean them too.

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pingalordlmao t1_irkpyd9 wrote

Man what 😭 I'd actually cry in the car on the way home, what is this man??

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AcrobaticSource3 t1_irng6yj wrote

> he kept slipping out every time I put it back in

Was that due to small penis? Too much lube? Inserted the wrong way? There could be many reasons for this, and each one has a different solution

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Tekripsz OP t1_iro96py wrote

No lube was used since I self lubricate really well, and sometimes too well lol. I think it was a mix of me being too self lubricated and it not being inserted right.

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No_Love_1353 t1_irk0gnm wrote

10/10 would only recommend this porn to ssbbw fans tho

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mittynuke t1_it1vi9i wrote

This was going off the rails at “He wanted to be tied to a chair and have a shake funneled down his throat. I did it, albeit a bit uncomfortable myself since it's not my sauce.”

I don’t know you or your situation or what this guy is like. But I feel like these are really weird requests for your first time with someone. Maybe I’m just old fashioned but I feel like you need to work up to something like… forcing a milk shake down someone’s throat!!?… over a period of time, if at all. You shouldn’t have to degrade yourself or do something that makes you super uncomfortable, especially the first time with a guy! I have no idea where this guy gets these strange desires from (porn?), but to me that was the bigger red flag than his sexual inexperience. If he’s into you then you can show him what works for you, but I feel like this whole encounter was stained more with the weird stuff than anything else. Maybe he thinks this is normal from whatever he has been watching and just needs you to tell him to calm down a bit.

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