Tough Sex: My Worst Sexual Experiences Shared

I wholeheartedly agree with this one. But is it better than a V8?

If you missed it, I am not perfect anymore (Viagra at 30?).  My sexual invincibility has been shattered.  I knew I was getting old.  I can tell from the pains in my back, knees, and ankles when the weather gets near freezing.  I knew that had to do with blood circulating, but never did I think it would affect old buddy.  I know I’m blowing it out of proportion to assume that one bad performance means the end of my sexual potency, especially since I still was pretty decent, but when you’re used to being a sex god like I am, its a hell of a rude awakening when your magic stick doesn’t magically stay stiff.  My specialty is (was?) being able to have an orgasm but keep going with no refractory period. Just slide the soiled condom off, slide another on, and change positions.  I loved the look in girls faces when I’d flip em over to a new angle and keep going.  It was that they expected me to roll over and sleep I guess.  Not my style.  I like to look at the clock during sex.  *****forward to the 2 minute mark if you don’t get why i posted this video*****

Before I appreciated the value of a quickie, I often timed my dick to bust at exactly 44 minutes, because I’d read that women prefer 15 minutes of oral and 45 minutes of sex.  I think they wrote it in Cosmo or something.  Yes, I got my sexual knowledge on women from Cosmo, but better that than a porno right?  But I digress.  The point that I am making is that I put way too much importance on my ability to slay them in bed.  With that kind of weight on it, its actually sort of surprising that this is the first time where my brain and penis weren’t on the same page.

And when I took a step back and looked at it from her point of view, it didn’t matter at all.  Sure she didn’t cum, but she has done so plenty times before.  And she had no problem assisting me orally, even if it only stayed hard a few minutes after.  And for that reason, she could care less (I hope it doesn’t keep happening).  That, and the fact that I’ve had worst sex in my life settles me a bit.  In honor of my waning libido, I’ll share with you five sad sexual experiences that sort of haunt me.  Its stories like these that keep me feeling good of how far my style has come.

#1. Where else should one start but their first time.  My virginity was once something I cherished and wanted to save until marriage.  As hyper as my hormones in high school were, I tried to keep them in a fence as long as I could.  When I was a wee lad, things were easy.  But when I caught an epic growth spurt my junior year, the girls began to notice me and things changed.  I was all about getting head though.  I talk about this a little in my book, The Story of Ryan Mega.  My friends and I, being young, foolish boys, created a game around conquering girls, with a point scale and all.  It was one of those twisted things we copied from the movie Cruel Intentions or something like that.  A few girls at school willingly sucked off everyone of us, sometimes all in one night (My motto: I’m going first, or I ain’t going at all- unless she swallows some Colgate in between). When a girl successfully sucked everyone of our dicks, we blessed them with a bracelet with the word TEAM beaded on the string.  There was at least a dozen of these girls at school on any given day and they usually wore these bracelets as if it were an honor.  There was one girl in particular that seemed to get more of a kick from it than the others.

Around the schoolyard, gossip started flying about the size of my penis and questions of who I was sleeping with.  I guess what dudes see in the locker room didn’t stay in the locker room (fags?- probably) because other than the bracelets, this high school sex club was a secret.  Out of nowhere, girls and guys I’ve never had a discussion with were asking if they could see my penis. Quite embarrassing.  Luckily, the hype didn’t last too long.  No high school gossip ever does.  But one night, when a few of the guys and me were hanging with the aforementioned head hunter, she decided that nobody was getting anymore head, unless I pushed my magical penis inside of her.  Now I’m thinking of every reason not to do it but mostly I wasn’t ready to give up my V card.  But my pals, those fucking bastards, pressured me to do it.  Take one for the team they said.  So I did it for the team.

Some virgins might be totally fucking lost.  Not me.  I watched tons of porn as a kid, so I knew exactly where to find that hole.  I didn’t however have any style.  I just rammed away deep and hard. With the thickness of the condom on my cock, the sensations weren’t as thrilling as they should have been for the first time and I was able to go for 30 minutes at minimum.  She was very satisfied, insisting that in the future, I fuck her more than she sucks us off.  The next week at school, the cock gossip started again but I learned to roll with it.

Why was this a bad experience? Despite the fact that I was known for quite possibly one of the coolest things you can be popular for in high school, it wasn’t time for me to have sex.  I’ll always remember the shame I felt when I pulled my sperm filled condom out of her, feeling nothing in my heart for her.  It feels like that moment, that feeling, was a harbinger for all the empty, casual sex I’ve ever had since then.

#2. College is a place where ‘hooking up’ is expected.  By the time I got to Northeastern State, I was all about the hook up and not about the relationships.  Why buy the cow to get the milk? was kind of like a motto in those days.  With my own dorm and autonomy, it was almost a waste of ability and opportunity not to go fucking crazy.  I had more flings and one night stands my first year of college than I can remember.  I am sure the number of girls that I had sex with tripled my GPA, and I nearly had an A average.  The bad thing about one night hook ups and multiple partners is the possibility of STD’s.  Luckily for me, I was very pro-safe Sex then (I used Dental Dam the first time I performed cunnilingus. Weird, because I’d smack a chick for trying to suck dick through the condom).  To this day, I’ve never been burned (fingers crossed++), but that isn’t to say I didn’t have close calls.  There were a couple of times in my life where girls have told me beforehand that they have an STD.  Words can’t express how much I appreciate this.  I think its because these girls liked me.  They see I’m not a bad person so they don’t want to harm me.  I know for a fact that they didn’t share this secret with everybody that pursued them (whole lot of burning going on at NSU).  There was one occasion where I found out the hard way.

She liked football players.  Something told me she had been with enough of them to get a 15 yard penalty- 12 men on the field at one time kind of shit.  I never pursued her.  She wasn’t much of a looker, probably a universal 7.  But she was a very sweet, country girl, that had a little bitty fat ass and some little bitty big titties, so I told myself I would if the opportunity presented itself.  One day, while walking from the cafeteria, we met alone and decided to go to my dorm.  Within minutes, we were undressing one another in my bottom bunk.  I slid my underwear off and slid the condom on as she lay back and spread her legs.  I can’t lie.  It was the best I’d ever had.  It was hot and moist and tight and her thick thighs wrapped around me only added to the pleasure of pressing against her body.  Now this is still my rookie phase, so I still didn’t have much style.  Before I could get into it and start pile driving it, I noticed my room was filled with the nastiest aroma I’d ever smelled.  It was overbearingly strong, like chlorine and yeast, and I could focus on nothing but it. There I was stuck in the middle of a dilemma.  I knew I should definitely stop and ask “hey whats that smell”,  but I couldn’t pull away from ooey gooey goodness.  My penis didn’t care though; it just kept sliding in and out like file cabinet.  Before I could decide what to do, I prematurely ejaculated, and the dilemma became less complicated.

We both knew there was a strange smell in the air.  She knew it was her.  She should have known better than to unwrap such an infected vagina from the cover of her underwear.  When I ejaculated, I didn’t tell her I was cumming though, so she didn’t know all of the doubts going in my mind.  I pulled out and ended the session, telling her it was a mistake for us to even move so quickly, knowing it was I who was struck by suddenness of ejaculating. If she didn’t know I came early, she probably thought I stopped because of the smell, and was extremely embarrassed.  As we rode the elevator down from my dorm room, I could sense that I’d successfully moved the blame, shame, and burden to her.  Before she left, she looked at me, to see if I would say anything, but I gave her an assuring look that the secret of her smelly slice would be safe with me.  My fears of ridicule were transferred to her.

Why is this top 5?  The funk.  I smelled it, but kept going. If I didn’t come early, I would have probably have kept going.  I might have taken advantage of the entire roll of Magnums.  I’ve always been a big proponent of safe sex, but even I knew that condom covering my cock didn’t guarantee that the next pump wouldn’t infect me.  It was the first time, I’d ever taken a risk sexually.  I am ashamed of this still.

#3 Relationships are a muthafucka.  Even when they are over, there are still certain rules and customs that you must adhere to.  There’s the splitting of the CD’s (right down the middle, regardless of who bought what), the splitting of the friends (mutual friends choose you or her; you can’t contact friends she had before you got together, even if you’re close friends now), and the splitting of places to hang (who gets the bar where you had your first kiss anyway?).  The rule that gets me is the wait rule.  How long does a person wait before sleeping with another person when you end a long term commitment? My answer- long enough to have sex with a different person and not feel guilty.

Here’s my situation.  My first long time girlfriend and I broke up because I planned to leave Nashville after graduation and she didn’t.  It wasn’t a bad split.  It was a silly attempt by me to make our separation easier. In retrospect, it was the worst decision I’ve made in my life maybe (because she is the greatest love I’ve ever lost, word to Jesus).  Before we were split for a month, I found a good job locally and alleviated all of my stress and worry (the real reason I split with her was I was stressing and she was too caring, always there for me asking what did I need and I was afraid of her love-some men just can’t be happy huh?).  I worried her and made her feel so bad, she started smoking black and milds and abusing pain killers to cope when not around me.  Scorned, she wouldn’t take me back when I begged another go at love.  We had one last great night together on my 24th birthday.  I knew if she were there in the morning, she would be mine again and if she weren’t, then it was truly over.  I woke the next day holding an empty pillow.

The moment I started my new gig, I was getting pushed up on by every girl in the building (that’s normal).  Not quite ready to start a new fling and still not quite over my gal, I’d managed to cordially dodge all advances.  But the day after the empty pillow, I was jaded and kind of lonely. I decided to take a different course of action.  I went on a couples retreat of sorts to gamble in Tunica with a couple of girls I worked with and one of their boyfriends.  I wasn’t much of a gambler, so I knew this was really a fuck fest / road trip.  The unfortunate part is that my date was newly separated from the father of her daughter and she knew my ex girlfriend from around the way (fucking Nashville, I hate tiny cities), so I worried that this would somehow get back to my ex and be the point of no return, the last nail in the coffin.  Whats worse, the other girl on the road trip was this dudes sister.  Even though she told me that she wouldn’t tell her brother I was humping his baby mama, the awkwardness of it all didn’t fade and I couldn’t find my mojo.

Why is it a top 5?  Here I am with the most beautiful girl in the call center, a petite redbone with freckles on her nose that begged you to kiss her just to be near them.  She was a dime of a woman by any standards.  She was like Jada Pinkett with a southern belle’s accent.  Here I am in Tunica with free drinks and our own hotel room and do not disturb signs and condoms galore.  At any other point in my life, this would have been an alright place to be with a girl like this for the first time.  Not this time though.  As she climbed her petite frame on top of mine, the only thing I could think about was my ex.  I have never been more stiff, more out of the moment than I was there in that hotel room.  It felt like I’d shut down and separated my mind from my body, ignoring the sensations from the touching and teasing.  It was the deadest sex I’ve ever had because all I could think about was the one I loved.

#4 How many of you like bloody sex?  You sick bastards know you’ve done it before.  My ex, from #3, was always extremely horny when those hormones came that time of the month.  It was one of those things I learned to grin and bear in order to keep her happy.  But what happens when there’s blood that’s not expected?  Panic. Thats what happens.

Here’s an interesting fact I just made up- Every day 100,000 women lose their virginity.  Of course, a bloody mess is common in those instances.  But anybody who knows anything about the vagina, knows that virginal sex doesn’t always mean the cherry gets popped.  I never read many books on it or anything.  I’m just talking from experience.

My neighbor had a cousin that sort of had a thing for me.  He knew what kind of guy I was, but he introduced her to me anyway.  After a date or two, we had sex, and it wasn’t bad.  She was more of a square (I think she’s a teacher in Atlanta now; go figure) so she didn’t really know much.  I was definitely a slut so I took it as my duty to teach her and please her.  Turns out, I had a few more lessons of my own to learn.

Here is where things get bad. One night after some Papa Johns and a home movie, we get with the get down.  Again she’s a conservative gal, so she likes to do it under the covers. Fine by me.  I was doing my thing and she’s coming out of her shell like never before.  I’m moving from position to position like my dick is stuck to a gear in her pussy.  We both are having a good time and the better it gets, the deeper I get.  She takes the dick like a pro, letting off little whelps and puffs of air with every thrust.  I kissed the sweat from her neck and lips as flood of wetness engulfed us below. Any circus show should end with a grand finale and I like to end with back shots so I moved to mount her from behind when the covers fell off the bed and a big red pool of blood was revealed.  Shocked, disgusted, and worried that I’d caused medical trauma, I hopped out of her, ripped off the condom, and threw it to the ground.

“Are you on your period?” I asked.

“No, she said.”

“Was this your first time?”

‘”Nope.”

“Are you sure you may not be starting your period?”, I asked as if I’d convince her she was.

“No man”, she snapped back at me.

“Then what the fuck is going on here?”, I asked.

“I dunno”, she said, “but you just fucked up my new silk sheets.  You didn’t have to ram me so damn hard like that”.  I guess she had a point.  I didn’t know what to do but apologize, get my things, and leave before she decided to charge me for the damage.  A few days later she called me to apologize for snapping on me and explained that her doctor confirmed it was a broken hymen.  I’d boldly gone where no man had gone before.  As awesome as that felt, I knew I had a problem.  All that fucking and I was only good at one thing, power fucking. That was the day I decided to stop ramming it in there and learn some style.

#5 Have you ever fell for someone that you were sexually incompatible with?  I have.  After years of flirts and skirts, my heart was all but dead from the games I played with love.  I have never been a relationship guy.  I am the first to admit that I flee when it gets too good.  Its like I don’t expect the good to last forever, so I inflicted the hurt before I could be hurt.  When you end a good relationship because you don’t see yourself marrying the person, you’re loving out of fear and not living in the moment, the only true way love can blossom and be appreciated.  I say these things easily now, but its because I took a long break to work on me when I first moved to Texas.  After a few battles with celibacy, I met someone that made me rethink my self exile from the dating and fornicating world.  And for a while things were great.  She and I took things slow.  It helped that she didn’t live in the city yet.  The pressure of sex was non existent.  It felt good to get to know a girl first before getting into a sexual relationship.  Any time I felt like I should pursue sex with her or another girl, I weighed it against our friendship and always chose to be good, for lack of a better word.

Things changed when she moved to the city.  Our dates became more frequent and soon we were hanging at each others places all night.   There was no other girl for me.  I felt energy move through my body like magnets whenever we kissed.  I begged her to stop.  For me, kissing always leads to one thing – my erect penis.  But she didn’t listen.  She didn’t understand the Pandora box she was opening.  Before long we were having steamier make out sessions, stripping and grinding like high school kids, as we passed spit.  One day, when we were both pretty tipsy, we took our romance to the next level. And you know what?

It was the worst sexual experience of my life.  Halfway into it, she pushes me off and turns over, telling me her woman friend was sore from the number of orgasms she had.  I understand, so I think nothing of it, and hold her as we fall asleep.  But the next morning, she is up at 7 am, practically tying my shoes on my feet, as she prepares to go to church and repent for her sin of premarital fornication.  I guess you can say I grew up in the church, so I didn’t question her beliefs on sexuality.  I knew where this bullshit was coming from (damn Baptists). I figured, it was a one time thing and we’d happily go back to being a celibate couple.

But that wasn’t the worst part.  We had sex a handful times over our year of dating.  And as hard as it was for me after she broke my celibacy, I didn’t sleep with any other women.  But oh was I frustrated.  We only had sex when she was drinking because that was the only time she was free enough with her sexuality.  My oh my, how a guy appreciates the girl of his dreams only wanting his body when she is drunk.  What’s worse, these sex sessions usually followed the exact same pattern.  Hot and heavy kissing and petting followed by three minutes of pumping before she pushed me off and claimed that her clam was sore.  And it always seemed to happen on a Saturday, so she didn’t have to wait an entire week to go to church and repent.

How much more could I handle?  I felt bad for wanting to make love with her.  I felt mad because she kept playing with our sex life, which was nonexistent until she started something she didn’t plan on finishing (I constantly begged her to stop the make out sessions when they were reaching a boiling point).  The last time we had sex, was the day before we split for good.  It wasn’t bad.  She finally let me come, and even allowed me to turn her over a few times and sneak it in from my favorite positions.  But the moment I came, so came the guilt trip.  And at a certain point, you get tired of feeling guilty for making love to the one you love.  I thought she was my soulmate.  We just have two different ideas of what sexuality means and its importance in a relationship.  I can’t stop missing her, but I know we are better off as solid friends.  Quite possibly, the worst sex I have ever had might be with the girl I last loved.  I’ve had some issues with my heart interfering with my sex life, but never before has someone made me question my soul’s goodness.

————Ryan Mega

One thought on “Tough Sex: My Worst Sexual Experiences Shared

  1. Pingback: Tough Sex: My Worst Sexual Experiences Shared « SexDrugsMoney

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