The Worst Sex

[Mysthero]

I thought it would be fun to talk about the worst sex we ever had. I'm talking consensual, everyone was into it, and when it was all said and done you look up at the ceiling and you're like "....that was terrible."

For the virgins among us, you can do worst date, or worst masturbation experience, this will kinda be a gun free form thing where we can all laugh at ourselves a bit!

‐-----

So I'll start this show! With what I thought... was going to be the best experience, turned out to be my top 3. (That's right, I got 3 stories to share but I'm only going to do one for now.)

Okay, so when I was younger there was this girl I knew, we will call her Chelsea. Chelsea was what most people would call... a 10. She was stunning, long brown hair, gorgeous eyes, lips that made you fantasize about all the possibilities.

I have always been a nerd with glasses but I was tall, and cute (not a 10 but ya know, a handsome geek). But Chelsea, outta my league. I even told her as such "You're too gorgeous to be seen with someone like me." Just my idea of flirting back then.

She had a boyfriend who was on the swim team and I was fine with her just being someone who kinda knew who she was. Weird thing though, she started saying hi more to me. Hung out with me. Seem to even take interests in my hobbies! She eventually broke up with her boyfriend who was cheating on her and I... being the opportunist I was, asked if she wanted to go to the movies and get her mind off things! 

Chelsea looks at me and says "Can we just watch a movie at your place?"

Score! 

We go back to my place, I'm trying to be respectful and maintain no expectations as we cuddle on my bed watching a movie and she looks me in the eyes and asks "Will you fuck me?"

I'm thinking this is amazing! We undress, we make out, she's got nice breasts... I decide to eat her out to get things started... everyone... let me tell you... there was a smell, and taste that I had never experienced before and have never since that day. Eveything... looked right.... but I mean... fish... she smelled like fish and tasted quite off. (For clarification, if you guys don't know... women have to maintain a very delicate ph balance down there. I'm not trying to be mean about this because look, she didn't ask me to go down on her, I did that myself. We were also both young, it's a thing.)

Anyways I don't stay down there for long, I couldn't. But I put a condom on and ask her if she has a preferred position. She tells me she wants to lay down on her back... so I'm happy to let her. The entire time, this girl just lays there. Doesn't hold me, doesn't wrap her legs around me. She moans and tells me I feel good but it was... boring. I ask her if she wants to change positions she tells me that I feel too good to stop.

I'm having a hard time cumming at this point because... well masturbation felt better. We continue, I pick up the pace and go harder... I mean I'm trying different things to make this more exciting. And it's not like she didn't let me either, if I lifted her leg, she'd let me. Bite her nipple she'd say "just like that" but as far as attention towards me... she gave me... none. Anyways I finally cum and roll off of her and I'm looking at the ceiling trying to figure out what happened.

She lays across my chest and tells be no one has ever lasted that long with her and it felt amazing and I'm... at a loss. She just, laid there the whole time!

So, I never slept with her again after that, but she did tell her friends about me and one of them asked me out a month later.

But when someone talks to me about boring sex... this experience always come to memory.

[Pixel]

Oh boy. First of all, let me just compliment the fact that everything was done right. Going down like the hero your name suggests, wearing a condom (if you're reading this I'm looking right at you, btw ) and trying to make the situation more exciting when there wasn't really any reciprocated passion.

Siiiiiigh y'know, I've had a lot of really bad times, but the worst time was the first time with my kid's mom. Now, I feel like I don't have the same urges as other dudes, especially at that age. I had my whore phase after having my heart broken by someone I still think about to this day and I feel like it got so bad that my brain was like yeah okay dude I actually think we've had enough of this for one set of 20's.

So, I decide to fly solo for a while. Until she comes along. I have a very specific... Type. There are things in women that I'm attracted to and I don't tend to pursue them if I don't see it in them. At least that's how I was at the time. I like big bright eyes, hers were brown and beady. I like short stacks, she's as tall as me. I like blonde hair, she had light brown. I like a little more weight on the bottom and less on the top, she was the opposite. But there was something about her that was alluring to me.

The chase was a lot of fun. The attraction was mutual, but it's like we were making it really hard for each other for shits and giggles until one night she showed up at my place earlier than our other friends when we were meeting for a game night, she hopped on me and it was on, and man did she know how to get me worked up before clothes were even removed.

But then we were naked, she had gorgeous if not a bit asymmetrical big tits that she liked me to be rough with, her body was slender and her skin was flawless to the touch, she laid back... And came in like 20 seconds. This isn't an exaggeration, it was literally that brief.

I've never really been that self conscious about my ah.. size. It's the kind of thing that us boys have seeded into their brains that IT'S GOTTA BE HUGE, when life experience has taught me that in most cases that absolutely is not true. I know that I'm above average in length and girth and I have this convenient little curve in just the right spot so that basically my natural shape does most of the work for me, but with certain people I do worry about it because I want to be really good for them. But 20 seconds or less? I know I'm not that good.

I hovered above her like... What? And she's just got this look of bliss on her face, this little smile, her head is tilted back a bit, her eyes are closed and she's all breathless and she just goes "Did you get off?". And I was like... Nnnooooo? This is especially funny because she'd told me previously that she felt like I could last a long time before that, and it makes me wonder how long dudes usually last. Anyways, she's the kind of chick who can't keep going after she has an orgasm, so I was just kind of left like , no round 2 or offer to help me get mine. Our friends showed up and we had a fun night, but, damn if that didn't burn in my brain.

She was always selfish in bed it turned out. She ended up lasting longer as time went on but, she'd get her goods and that was about that. A lot of the time. I had to train myself to go almost on command when she said she was getting ready. Lemme tell ya, mutual orgasm is pretty intense if you've never experienced it. 

So, yeah. That was the worst ever. But with her I also had my best ever.

[Mysthero]

8

3 hours ago, Pixel said:

Oh boy. First of all, let me just compliment the fact that everything was done right. Going down like the hero your name suggests, wearing a condom (if you're reading this I'm looking right at you, btw ) and trying to make the situation more exciting when there wasn't really any reciprocated passion.

Siiiiiigh y'know, I've had a lot of really bad times, but the worst time was the first time with my kid's mom. Now, I feel like I don't have the same urges as other dudes, especially at that age. I had my whore phase after having my heart broken by someone I still think about to this day and I feel like it got so bad that my brain was like yeah okay dude I actually think we've had enough of this for one set of 20's.

So, I decide to fly solo for a while. Until she comes along. I have a very specific... Type. There are things in women that I'm attracted to and I don't tend to pursue them if I don't see it in them. At least that's how I was at the time. I like big bright eyes, hers were brown and beady. I like short stacks, she's as tall as me. I like blonde hair, she had light brown. I like a little more weight on the bottom and less on the top, she was the opposite. But there was something about her that was alluring to me.

The chase was a lot of fun. The attraction was mutual, but it's like we were making it really hard for each other for shits and giggles until one night she showed up at my place earlier than our other friends when we were meeting for a game night, she hopped on me and it was on, and man did she know how to get me worked up before clothes were even removed.

But then we were naked, she had gorgeous if not a bit asymmetrical big tits that she liked me to be rough with, her body was slender and her skin was flawless to the touch, she laid back... And came in like 20 seconds. This isn't an exaggeration, it was literally that brief.

I've never really been that self conscious about my ah.. size. It's the kind of thing that us boys have seeded into their brains that IT'S GOTTA BE HUGE, when life experience has taught me that in most cases that absolutely is not true. I know that I'm above average in length and girth and I have this convenient little curve in just the right spot so that basically my natural shape does most of the work for me, but with certain people I do worry about it because I want to be really good for them. But 20 seconds or less? I know I'm not that good.

I hovered above her like... What? And she's just got this look of bliss on her face, this little smile, her head is tilted back a bit, her eyes are closed and she's all breathless and she just goes "Did you get off?". And I was like... Nnnooooo? This is especially funny because she'd told me previously that she felt like I could last a long time before that, and it makes me wonder how long dudes usually last. Anyways, she's the kind of chick who can't keep going after she has an orgasm, so I was just kind of left like , no round 2 or offer to help me get mine. Our friends showed up and we had a fun night, but, damn if that didn't burn in my brain.

She was always selfish in bed it turned out. She ended up lasting longer as time went on but, she'd get her goods and that was about that. A lot of the time. I had to train myself to go almost on command when she said she was getting ready. Lemme tell ya, mutual orgasm is pretty intense if you've never experienced it. 

So, yeah. That was the worst ever. But with her I also had my best ever.

I had a date with a glass canon like that, where after she orgasmed she was done. But she was nice enough to help me finish. I totally get confidence issue, I'm actually average but I've always felt I was on the small side.

Had a girl once tell me I needed to buy smaller condoms and it was a hard blow to my ego. Even though she was just saying it to be mean.

I would hate having a night where one side is just like "I'm done." And that was it. My balls ache just thinking about that. Lmao

I'll see if we get a couple more stories before I tell the one where I got my ass kicked by a marine and got laid an hour later. Lmao

 

[Pixel]

A GLASS CANNON

[KittyB00]

How about a massive fail? lol

So one day on campus I was going to class and a guy bumped into me. Super freakin cute like unbelievable cute. He apologized and asked me for some directions to his class. Then he offered me to buy me coffee I immediately said yes. We exchanged numbers and went our separate ways 
 

 the next morning it was Saturday and he shots me text asking if we could hang and if I could show him around the city. So we met up and I showed him the malls I go to the gym I work out in where to jog where not to jog. He bought lunch for us and i thought it was a date we even caught a movie like come on date vibes right!?!? 
 

As the day starts to end I’m in my dorm room. Him and I are texting back and forth. He then asks me if I could come over tomorrow and help him study. Sexy vibes were ringing in my mind. This is my first time being with a guy after the incident, but his cute super kind funny. So I agree. 
 

I went over to his place and he answers the door shirtless. Sex appeal right? He invites me in. While he was going to put on a shirt he asked if I ate anything. I said no. He then proceeds to cook grilled ham and cheese my favorite he learned from yesterday. Like sure simple meal but the fact he can cook like I’m soaked already. So I asked to use the bathroom. I started stripping cuz come on if he answered his door half naked knowing I’m coming over he was definitely having dirty thoughts. 
 

So I walked out completely naked and I got a reaction I wasn’t expecting. He paled like why? I’m might not be the fittest girl on the volleyball or swim team, but I get told I’m hot all the freakin time plus I’m clean shaven cuz I heard guys like it that way. He throws his jacket at me. Screaming 

“Kitty the fuck you doing put clothes on.” I explained the situation blushing very freakin brightly. And he told me he was gay. though he did say I had a nice rack. And we’re still friends to this day. So it’s a W ig. 

[Pixel]

34 minutes ago, KittyB00 said:

How about a massive fail? lol

So one day on campus I was going to class and a guy bumped into me. Super freakin cute like unbelievable cute. He apologized and asked me for some directions to his class. Then he offered me to buy me coffee I immediately said yes. We exchanged numbers and went our separate ways 
 

 the next morning it was Saturday and he shots me text asking if we could hang and if I could show him around the city. So we met up and I showed him the malls I go to the gym I work out in where to jog where not to jog. He bought lunch for us and i thought it was a date we even caught a movie like come on date vibes right!?!? 
 

As the day starts to end I’m in my dorm room. Him and I are texting back and forth. He then asks me if I could come over tomorrow and help him study. Sexy vibes were ringing in my mind. This is my first time being with a guy after the incident, but his cute super kind funny. So I agree. 
 

I went over to his place and he answers the door shirtless. Sex appeal right? He invites me in. While he was going to put on a shirt he asked if I ate anything. I said no. He then proceeds to cook grilled ham and cheese my favorite he learned from yesterday. Like sure simple meal but the fact he can cook like I’m soaked already. So I asked to use the bathroom. I started stripping cuz come on if he answered his door half naked knowing I’m coming over he was definitely having dirty thoughts. 
 

So I walked out completely naked and I got a reaction I wasn’t expecting. He paled like why? I’m might not be the fittest girl on the volleyball or swim team, but I get told I’m hot all the freakin time plus I’m clean shaven cuz I heard guys like it that way. He throws his jacket at me. Screaming 

“Kitty the fuck you doing put clothes on.” I explained the situation blushing very freakin brightly. And he told me he was gay. though he did say I had a nice rack. And we’re still friends to this day. So it’s a W ig. 

Honestly him making you the sandwich because he knew it was your favorite is so fucking wholesome, never let him go.

[Mysthero]

51 minutes ago, KittyB00 said:

How about a massive fail? lol

So one day on campus I was going to class and a guy bumped into me. Super freakin cute like unbelievable cute. He apologized and asked me for some directions to his class. Then he offered me to buy me coffee I immediately said yes. We exchanged numbers and went our separate ways 
 

 the next morning it was Saturday and he shots me text asking if we could hang and if I could show him around the city. So we met up and I showed him the malls I go to the gym I work out in where to jog where not to jog. He bought lunch for us and i thought it was a date we even caught a movie like come on date vibes right!?!? 
 

As the day starts to end I’m in my dorm room. Him and I are texting back and forth. He then asks me if I could come over tomorrow and help him study. Sexy vibes were ringing in my mind. This is my first time being with a guy after the incident, but his cute super kind funny. So I agree. 
 

I went over to his place and he answers the door shirtless. Sex appeal right? He invites me in. While he was going to put on a shirt he asked if I ate anything. I said no. He then proceeds to cook grilled ham and cheese my favorite he learned from yesterday. Like sure simple meal but the fact he can cook like I’m soaked already. So I asked to use the bathroom. I started stripping cuz come on if he answered his door half naked knowing I’m coming over he was definitely having dirty thoughts. 
 

So I walked out completely naked and I got a reaction I wasn’t expecting. He paled like why? I’m might not be the fittest girl on the volleyball or swim team, but I get told I’m hot all the freakin time plus I’m clean shaven cuz I heard guys like it that way. He throws his jacket at me. Screaming 

“Kitty the fuck you doing put clothes on.” I explained the situation blushing very freakin brightly. And he told me he was gay. though he did say I had a nice rack. And we’re still friends to this day. So it’s a W ig. 

I think I've seen this movie.

For real though I love this. What an amazing story!

[Mysthero]

Okay, so here is my second story!

Shortly after high-school I get a call from a long time friend and RP partner. She's getting married!

Her name is Pippin (yes, like the Hobbit). She wanted me to come up to see her, meet the fiance, all that stuff. So I take the trip to visit.

I arrived and she's by herself (red flag 1)

We sit down, catch up, talk about some of our old RP stories. She tells me about her fiance. He's a marine, just got back from deployment and wanted to get married while he was back. Cool.

She then tells me (without trying to make him sound bad) about how controlling and jealous he was. (Red flag 2)

She's asking me for advice and brings up her family are not huge fans of his. She then drops the bomb of how our RPs always turned her on and she always crushed on me. (Red flag 1000)

So I'm in the middle of being THAT GUY, trying to convince her she shouldn't marry this guy unless she's absolutely sure! Then... he comes home. Now bare in mind, we are JUST talking in the living room, but apparently she never told him I was coming.

She tries introducing me but he blows a gasket and starts yelling at her... and then backhands her! Look, I'm not a good person, I don't pretend to be a paragon of morality, but I was raised a southern gentleman and I was not about to just stand by while some guy hits a woman infront of me.

So, I did something... stupid.

I charged this guy and shove him. The next thing I know I was thrown from my feet and came crashing down on the table in the living room. Before I can even figure out what happened, I find myself fighting for my life against a stronger, faster, and far better trained opponent. Needless to say, I'm not just getting my ass kicked, I'm getting demolished. The fight goes from the living room, to the kitchen. I gran the nearest thing I can with a handle and swing for the fences! *BAM!!* I knocked him out cold with a fryingpan. We both hit the floor... I am covered in blood. I don't know it at the time but I would actually need stitches.

Pippin comes to me asking if I'm okay, to which they only real clear memory I have of this was looking her in the eyes and saying "I didn't win that fight."

So, the next day... my whole body aches, I'm leaving to go home and my plan is to just sleep for a year.

But I get a text message from Pippin asking me if I could go say goodbye in person to her at work. She wanted to apologize for everything.

She worked at a seasonal haunted house and this year she was a silent Hill nurse.

She shows me where she will be posted, sits on a medical gurney and spreads her legs showing she's not wearing underwear.

Look, it wasn't the worst sex I've ever had... in fact I thought it was very hot and enjoyed myself with the exception of my whole body was sore. But I mean... having sex in a haunted house, c-mon! Lol

Never saw her again... they got married and I was not invited to the wedding.

[Pixel]

I'm a little jealous of the silent hill nurse bit but I do not envy the rest

[Mysthero]

6 minutes ago, Pixel said:

I'm a little jealous of the silent hill nurse bit but I do not envy the rest

Not my proudest moment

[Pixel]

9 minutes ago, Mysthero said:

Not my proudest moment

I've had worse.

[The Wolf]

another easy with a moral, LONG time ago going at it and was going to go down on her and got down there and it STUNK I mean gag reflex garbage can rot just holy fricken hell bad that just stopped the action cold for a bit but I was young and stayed ready so we finished but damn, moral is cleanliness is fricken KEY

[spectacular_silver]

So off the top of my head- not quite the worst sex but a bad sexual encounter.

When I was a teen, I was fooling around with a close guy friend in my room. I was still a virgin and hadn't really dated, but I had a huge crush on him. We ended up making out with me on top of him, and started dry humping each other. Unfortunately my mum was downstairs. She walks in without knocking to see me grinding on top of this guy, with his hands on my ass cheeks. I quickly jump off him and freeze. She stares at us with a horrified expression and gasps "I thought you were just friends!" This guy gives her the most confident and grin ever and says in the most smug tone I've ecer heard "we're *really good* friends.~"