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Dear Penthouse..(Dubious stories of lust and adventure)

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casmith07

Member
First Time

I went to a military school for college. I came home for Christmas break my freshman year and we had plenty of sexy talks over the phone (phone cards FTW) leading up to Christmas break.

We went out to dinner the night before Christmas Eve. She drove, which was strange to me. On the way home, we pulled into our old HS parking lot. She wanted to get into the back seat to "make out"...so we did. Next thing I know I'm inside her, thrusting away. I didn't cum. She wanted to stop because it hurt, but "wanted to practice more after Christmas." I felt like a champion afterwards.

She later gave me head twice in one sitting in a church parking lot near her parents' house. I came all over the place. Her hair, her face, it was awesome. The running joke became that she "learned to drive stick in a church parking lot." We've hooked up over the years and she's gotten better with age. Contrast her, giving me the best head ever, with the other story above, lol.

"Can I come over?"

First summer out of law school, I'm at a bar watching the Lakers in the conference finals with a friend. We're just watching, having a good time. We get approached by two cute blondes. We talk, she gives me her new business card, I give her mine. They leave and we leave to go to another bar.

On the way out I get a phone call from a number I don't recognize, but I recognize the area code. I pick it up. It's the girl from earlier, sobbing: "I don't know where my friend is! She left me to go home and fuck the bouncer! Where are you?"

I respond and tell her I'm heading home, and she asks where I live and I tell her the general neighborhood.

"Oh, that's close to where I parked my car can I come over?" -- her entire tone of voice changed.

Yes. Yes you can.

We fucked for three hours. We became friends and have met up twice since our "relationship" ended and the sex was positively mind blowing every time with her. Another that lets me raw-dog and always takes Plan B afterwards. Hard to not like a chick like that, lol.

Friend's Brother's Girlfriend - now Fiancee

This one I'll keep brief. We met, their relationship was on the rocks, we fucked, I came inside her (I have a creampie fetish, alright?). After meeting up once more she decided to "focus on her relationship."

I saw her again a year or so later at a Cinco De Mayo party and she whispered "it's so unfair how unbelievably attracted to you I am" into my ear while I was playing beer pong.

She had one of the nicest asses ever. Getting her doggy style was cumshot-inducing in and of itself. I wish I could have one more go with her, but considering she's getting married in 6 months its probably a bad idea. Oh and the connection in the tagline above makes it super risky, lol.
 

casmith07

Member
Okay, not trying to derail, but right? Can someone explain what is so difficult about it, I'm sure there's some lady out there complaining about my oral skills as well so I'm not trying to be a jerk. I feel like teeth and improper suction and lack of wetness, which seems counter intuitive, have been the main factors in my experience (to clarify, those have been my main issues with other people doing oral stuff. To me. Yes I got laid once, congrats on the sex).

Yeah I totally agree.

I usually hate to compare real sex to porn because it's unrealistic, but if a girl watched just a little bit of blow job porn she would be able to deduce what's good and what isn't.

No teeth, don't "pull your lips in" like over your teeth and make your mouth rigid, and apply moderate, consistent suction/pressure and moderate/consistent speed and stroking.

It worked on one girl when I told her to treat it as if it were a clitoris.

My high school sweetheart ex, though, doesn't actually ever suck that hard (or at all) when she gives me head. She's just phenomenal with her tongue...and throat. Annnnnd now I need to text her. Goddammit.
 
Fuck it, I'm wading into this pool.

So a while back I was at some house party and I got pretty drunk, as one is wont to do at these kinds of events. My friends and I were dancing and being ignorant per usual, and some girl came over and started to dance with me.

Let me just point out that she was not particularly attractive. She was short a little chubby and looked like she had a lot of "miles" on her. But it had been quite the dry spell for me so I was just happy anyone was interested.

We're dancing for a while and then she asks me, "Are you straight?". See, I was really drunk and I thought she was referring to whether or not I was "straight" as in "okay" like "not really drunk". So I matter-of-factly say, "Definitely not".

She gets kind of upset and says "Oh well that's a shame, you're cute". Immediately it clicks that she was asking me if I was heterosexual, and I backpedal and explain. Following my backpedaling she grabs me by the hand and leads me to someone's bedroom at the party. (Note: There were a lot of gay people at this party, so I guess that's why she asked. Either that or I give off a gay vibe. Who knows)

She leads me to this back room and we start making out on the couch in there. The only problem is that she keeps biting my lip. Hard. I'm down for playful roughness, but this chick was trying to draw blood. So I stop her and ask "So, that thing you do? That biting thing? What is that, exactly?" to which she responds "Oh, that's kind of my thing". I pause for a moment, think it over, and say "I think you should potentially get a new thing" She kind of just laughs it off, not taking me seriously and continues to make-out/bite my lip.

Things progress in the making-out department until she finally asks me if I have a condom. Of course I don't have a condom, I'm not the suave guy who is going to get laid at any given moment. I'm the guy that bought a box of condoms three years ago and laughed at how far away the expiration date was. "Who's not going to be able to use fifteen condoms in three years?"

I threw away fifteen condoms three years later.

Anyway, she tells me it's not a problem. She unzips my pants and starts giving me a blow job. Which was honestly the worst blow job I've ever could have conceived. It was definitely the worst I have ever received, but it was also the worst I could ever surmise possible. She kind of just opened her mouth agape like a cup over a banana. Then she moved down to my balls and sucked on them like a Dyson. And not in a good way. I fucking yelped with pain. I let this persist for a few more minutes until I got frustrated and finished myself off. We exchanged no information and I left the room after her.

I watch her walk across the room and the light hits her again and the drunk goggles come off. She is hideous and gross, and she just mashed my penis around in her mouth for five minutes. The horror starts to set in and I go over to my group of friends to ask about her. They tell me she's "kind of a slut" and she's hooked up with most of the guys in the house. This translates, in my mind, that I have no contracted HIV or something (Hey, I was really drunk). I didn't know what to do. Frantically, I rush into the bathroom and lock myself in. First, I wash my dick with soap and water, but I feel like the damage is done. Noticing a bottle of Listerine on the counter, I think hard about what I'm going to do, empty my cup of beer and fill it with Listerine. I submerge my junk for 20-30 seconds.

Now, you're probably thinking, "Holy shit, that probably hurts a lot". And you're right. Holy shit, that does hurt a lot.

I come out of the bathroom still traumatized and my friends decide to bring me home before I can continue to make a scene.

In the distance I see the girl talking to another guy on the dance floor and as I walk out, she leads him to the bedroom.

Mother of god.
 

Arkos

Nose how to spell and rede to
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Insanity.
 

Mistel

Banned
Recently, a girl asked me to fuck her like I hated her. So I did: hair-pulling, choking, name-calling, face-slapping, etc.
That's what I like, some girls are really into that sort of stuff. I remember one leaving claw marks everywhere all up my back that was so good. Not to mention we did it outside so we both looked like a state afterwards.

Oh my Imperial that's certainly something...

And this is the ad I just got in the thread:
weirdadz0sry.png
 
The most effective way of learning that your mouth is way more resistant than your dick is dipping your johnson in Listerine. I did it once pre-blowjob thinking it'd make the experience more pleasant for my partner. Red and swollen (and not in the good way) and wincing in pain every time her tounge touched my dick didn't turn out so good.
 

casmith07

Member
image.php


Insanity.

LMAO. That story was out-fricken-standing hahahaha!

That's what I like, some girls are really into that sort of stuff. I remember one leaving claw marks everywhere all up my back that was so good. Not to mention we did it outside so we both looked like a state afterwards.

Oh my Imperial that's certainly something...

And this is the ad I just got in the thread:
weirdadz0sry.png

Hahaha...man, getting your back scratched during sex is hot until you take a shower the next day...then it's REALLY hot :-\
 

mf.luder

Member
I fucked a girlfriend on her period and she had a tampon in. I didn't know it was in there so I just plowed her. After we finish she's like uh oh and she said it was my fault that I didn't take out her tampon.

We went into the bathroom and I literally had to fish it out with fingers. It was in there deep and I couldn't get a grip on it. She started to freak out so we went to emerg at like 2am. We were there for an hour or so.

She went to the bathroom multiple times because it was putting pressure on her insides. She was eventually able to push it out without any assistance.

Again, my fault.
 

DopeToast

Banned
I don't really have anything crazy that's happened to me, but I've only been having sex since October. The first girl was great at everything, and I really cared about her and it was never awkward. That's the kind of sex I really like. The second girl was an old friend and is one of the most attractive people I've ever seen. It was fun and we laughed about it. Then I hooked up with a girl in high school (she is 18, I am 21, just so you know) that I randomly met at a party. The ultra-thin Trojans I had broke twice, but I didn't finish anyway. She wouldn't let me leave the lights on, she passed out right after, and my bed and room smelt of strong perfume for awhile. I don't think I'm the type that enjoys random hookups. The only exciting part was the chase, but the reality of being that intimate with a stranger wasn't as fun. Oh well, you learn I guess!
 

jufonuk

not tag worthy
ok, once I went in when my ex, wasn't wet.

long story short, I managed to pull my penis skin back too far, started to bleed like mad,

I called up the NHS help line, they told me it was fine and happens a lot to people.
soooooo much blood :(
 

Mistel

Banned
Hahaha...man, getting your back scratched during sex is hot until you take a shower the next day...then it's REALLY hot :-\
I looked horrible afterwards, scabs everywhere, fun but still not something I want to happen that often.

DopeyToast most casual hook ups are a bit hit and miss and Mf.ludler I've got no idea how that could be you being singularly at blame.
 

Kinsei

Banned
Not my story, but I figure it is worth sharing.

My friend was delivering a pizza, and it turned out he was delivering it to a girls sweet sixteen party (Just so you know, legal age here is 16, and he was 18 at the time.). She answered the door in a shaving cream bikini (They must have been out of whipped cream) so he decided to throw out as many pizza boy in a porno lines he could think of, and both she and her friends thought he was hilarious. One thing led to another and the birthday girl ended up asking him out.

Fast forward to the date and it was going horribly, he told me that she was completely self centered, and a horrible person to be around.

On their way back to her house she get's on the car floor and pulls out his dick and starts giving him a BJ. Rather than do the sensible thing an pull over, he kept on driving. A deer ran out into the road and he was forced to slam on the brakes, The girl flew back and slammed into the gear shift leaving a mark on her face.

I wonder how she explained that to her parents.
 
ok, once I went in when my ex, wasn't wet.

long story short, I managed to pull my penis skin back too far, started to bleed like mad,

I called up the NHS help line, they told me it was fine and happens a lot to people.
soooooo much blood :(

That's like my biggest fear. My frenulum feels super tight as well sometimes.
 

Symphonia

Banned
One of the first times I had sex resulted in a trip to A&E. I went in with her a little bit drier than normal and just started plowing away. My foreskin pulled back, as per the norm, but as she was too dry - and I was going too hard - I stretched it back too far. It just wouldn't stretch back over. I figured I'd leave it until I go soft again so went to sleep. I woke up the next morning and it still hadn't stretched back and I was still semi-hard. I rung A&E and they told me to go down immediately. I did so and the nurse told me this was uncommon but curable. I had three needles jabbed in my groin to numb the area and a doctor came along to stretch the foreskin back over. He then booked an operation to have my foreskin removed. One of the most unpleasant experiences ever.
 

Arkos

Nose how to spell and rede to
One of the first times I had sex resulted in a trip to A&E. I went in with her a little bit drier than normal and just started plowing away. My foreskin pulled back, as per the norm, but as she was too dry - and I was going too hard - I stretched it back too far. It just wouldn't stretch back over. I figured I'd leave it until I go soft again so went to sleep. I woke up the next morning and it still hadn't stretched back and I was still semi-hard. I rung A&E and they told me to go down immediately. I did so and the nurse told me this was uncommon but curable. I had three needles jabbed in my groin to numb the area and a doctor came along to stretch the foreskin back over. He then booked an operation to have my foreskin removed. One of the most unpleasant experiences ever.

Congrats on the circumcision.
 

Symphonia

Banned
Congrats on the circumcision.
The actual circumcision is probably one of the best things to happen. I don't know if I'm the only one but sex feels far more enjoyable with a cut penis than an uncut one. And the girls seem to prefer cut to uncut.
 

casmith07

Member
The actual circumcision is probably one of the best things to happen. I don't know if I'm the only one but sex feels far more enjoyable with a cut penis than an uncut one. And the girls seem to prefer cut to uncut.

Both of those statements are subjective, but this is not a circumcised vs. uncircumcised thread and I imagine that mindless debate would lead to the fastest thread lock of all time.
 
This is a nightmare situation and I applaud you for seemingly keeping it cool as it happened. I used to have problems changing baby diapers (you should see how many wipes I used to use in order to never get any on my fingers)... I can't imagine another adult's shit... oh god I'm shivering just thinking about it.

Anyway, just 'cause one guy turned out not to douche doesn't mean others won't. Just ask them beforehand :p
Thank you ;____; I did everything I could not to start screaming LOLL..

I know. I think it's just one of those irrational fears in my head now that I need to work through.. I know it sounds dumb ;_;.

I also really like bottoming o_o
 

Arkos

Nose how to spell and rede to
The actual circumcision is probably one of the best things to happen. I don't know if I'm the only one but sex feels far more enjoyable with a cut penis than an uncut one. And the girls seem to prefer cut to uncut.

I was kind of joking, I feel like I've read that un-circumcised actually gives more pleasure, maybe because of the extra action on the head. Glad that you and the ladies like it though, I've been happy with mine :p
 

Symphonia

Banned
Both of those statements are subjective, but this is not a circumcised vs. uncircumcised thread and I imagine that mindless debate would lead to the fastest thread lock of all time.
Hence why I said that it feels better to me and that the girls I've been with seem to prefer cut to uncut. Of course it's going to be different for everyone, the whole circumcision thing is a matter of personal preference, akin to shaved/trimmed/jungle, etc. Everyone has different tastes.
 

casmith07

Member
Hence why I said that it feels better to me and that the girls I've been with seem to prefer cut to uncut. Of course it's going to be different for everyone, the whole circumcision thing is a matter of personal preference, akin to shaved/trimmed/jungle, etc. Everyone has different tastes.

Jungle..................... :-\

Hehe.
 
I once got a blow job on a charter bus full of people and to make it worse we were in the front seat. It was for a sorority formal and the girl wasn't my date, Im pretty sure I hooked up with 4 different girls that night. After I broke up with my long time girlfriend I went through a pretty crazy stage.
 

Arkos

Nose how to spell and rede to
I once got a blow job on a charter bus full of people and to make it worse we were in the front seat. It was for a sorority formal and the girl wasn't my date, Im pretty sure I hooked up with 4 different girls that night. After I broke up with my long time girlfriend I went through a pretty crazy stage.

thumbs-up.gif


My buddy sexed up our landlord one time (well a couple of times).
 

BPoole

Member
I'll share another story that happened about 3 years ago with a girl that I just recently broke up with.

Just to preface this story, my ex girlfriend was a lot older than me. At the time of this story, I was 21, and she was 36, with twin boys that were 9 years old.

Over New Year's Eve/Day, all 4 of us went on vacation to some quiet little historic town in Maryland. The twins went to bed around 9pm as usual and my ex and I went down to the hotel restaurant/bar to drink and do karaoke. It was a small crowd there but it was pretty enjoyable.

Anyway, next thing we know it's like 3am, so we head back up to the room to get down to business (just to note, the hotel room had a master bedroom and a separate room with a pull out bed whre the kids were, so we were not having sex in the same room as the kids). She has an IUD, so I never had to use condoms. What we typically would do is have sex and then instead of be finishing inside her, and she blow me and have me bust all over her face/tits. As we were having sex, she tells me that she wants me to bust inside her mouth.

So we get towards the end of the deed, and she starts blowing me. I could already tell this was going to be disastrous since I could feel I was going to be blowing a huge load. So finally it comes (literally) and her mouth is completely filled with my man juice. She can't swallow it, so she puts her hand over her mouth and heads towards the bathroom. I follow her as she exits the room, but right when she opens the door, one of her kids was standing right out the door pissed off because we had woken him up. So there we are standing there, both completely naked, and she is unable to speak to him because her mouth is full.

So what does she do? She turns her back to him and spits all of my load all over the floor, then rushes into the bathroom and starts puking. Meanwhile, I'm just stand there with my hands over my junk as this kid whines to his mom through the bathroom door.

Fun night

(don't ever date a girl with kids that aren't your own)
 
Not mine but rather an internet friends. It was his wedding night and they were both extremely drunk when they get back to the hotel room. They go at it without taking most of their clothes off. He notices that there is blood but just figures it's her period and he doesn't want to ruin the experience and stop. They keep going at it until they fall asleep. In the morning he wakes up to an unbearable pain in the groin. Turns out that blood isn't her from her period but from a spontaneous circumcision. She hadn't removed her panties but had just tugged them to the side. Somehow they caught his foreskin and ripped it off but he was so drunk he didn't notice. Couldn't have sex for a while but he got really good at oral.
 
Nearly choked on my Chinese, you asshat, ha. And I've never had dick cheese, ever. I've always kept my genitals clean. I scrub thoroughly in the shower twice a day.

I was under the impression the substance accumulated around the penis, and not the genital area. Then again I'm not speaking from personal experience. Regards.
 

Symphonia

Banned
I was under the impression the substance accumulated around the penis, and not the genital area. Then again I'm not speaking from personal experience. Regards.
Well, yeah, hence the name 'dick cheese' - I just wanted to clarify that my entire genital area is kept clean, ha.
 

Sorian

Banned
Not mine but rather an internet friends. It was his wedding night and they were both extremely drunk when they get back to the hotel room. They go at it without taking most of their clothes off. He notices that there is blood but just figures it's her period and he doesn't want to ruin the experience and stop. They keep going at it until they fall asleep. In the morning he wakes up to an unbearable pain in the groin. Turns out that blood isn't her from her period but from a spontaneous circumcision. She hadn't removed her panties but had just tugged them to the side. Somehow they caught his foreskin and ripped it off but he was so drunk he didn't notice. Couldn't have sex for a while but he got really good at oral.

Holy fuck, ow ow ow.

Also, to the above, are you sure you aren't Sats with all the Olivia Wilde gifs? :p
 
Once me and an old GF were fighting about who knows and later that night we get over it and start to fool around and she gives me a great BJ. After I finished unbeknownst to me she got in close and licked my face with what I'm sure had some cum residue. I was disgusted. She thought that was going to be the end of it so I kept quiet waiting for my chance to retaliate.

Around a week or so later we started to have some foreplay and I finger her to get started. I then pulled my fingers out and have her a wet willy with em. She immediately starts gagging and puking in the bathroom. I'm like, "thought you had me didn't you?"

Needless to say it was awhile before she let me have sex with her again.
 
Once me and an old GF were fighting about who knows and later that night we get over it and start to fool around and she gives me a great BJ. After I finished unbeknownst to me she got in close and licked my face with what I'm sure had some cum residue. I was disgusted. She thought that was going to be the end of it so I kept quiet waiting for my chance to retaliate.

Around a week or so later we started to have some foreplay and I finger her to get started. I then pulled my fingers out and have her a wet willy with em. She immediately starts gagging and puking in the bathroom. I'm like, "thought you had me didn't you?"

Needless to say it was awhile before she let me have sex with her again.

Meh, you can't be too precious about this sort of stuff. I mean she's had it in her mouth.
 

Sorian

Banned
Meh, you can't be too precious about this sort of stuff. I mean she's had it in her mouth.

Yeah, I've never had much of an issue, I'm sure I could be grossed out that I'm making out with the girl that just had my dick in her mouth but odd combinations like that kind of come with the territory. It's cool with me as long as it's nothing unhealthy (ass to mouth/vagina is really only a porn thing unless there was some extensive prep time IMO)
 

Symphonia

Banned
Yeah, I've never had much of an issue, I'm sure I could be grossed out that I'm making out with the girl that just had my dick in her mouth but odd combinations like that kind of come with the territory. It's cool with me as long as it's nothing unhealthy (ass to mouth/vagina is really only a porn thing unless there was some extensive prep time IMO)
The best kind of sex - or the best kind of sex I've personally had - is when it comes from the heat of the moment. There's no fun in planning this sort of stuff. Being spontaneous can be a turn on when it comes to sex.
 
The best kind of sex - or the best kind of sex I've personally had - is when it comes from the heat of the moment. There's no fun in planning this sort of stuff. Being spontaneous can be a turn on when it comes to sex.

Planned sex rarely works. Being in a relationship for a while, I can say it's always disappointing for either side when you say "Yeah, let's have sex at such and such a time" and when it comes to it it doesn't happen or me or her are too tired. Spontaneity is awesome.
 

Mistel

Banned
Also, to the above, are you sure you aren't Sats with all the Olivia Wilde gifs? :p
No I just think she is really sexy, that face is to die for...

Not that I've got much experience with it, but cum is a nightmare to get out of hair.
 

MercuryLS

Banned
Things progress in the making-out department until she finally asks me if I have a condom. Of course I don't have a condom, I'm not the suave guy who is going to get laid at any given moment. I'm the guy that bought a box of condoms three years ago and laughed at how far away the expiration date was. "Who's not going to be able to use fifteen condoms in three years?"

I threw away fifteen condoms three years later.

This part killed me.
 

Izayoi

Banned
Well, the girl I fucked on Friday night asked me to choke her until she passed out... so I did.

Surprisingly, I got a huge kick out of it.

Maybe I need help.
 

Astra

Member
I dated/had sex with a woman who I later found out was a prostitute. At least I was getting it for free!
 
Well, the girl I fucked on Friday night asked me to choke her until she passed out... so I did.

Surprisingly, I got a huge kick out of it.

Maybe I need help.
I think it's her that needs to get checked, if anything. Why would she want to miss the rest of the fun!?
 
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