my first time

i’ll always maintain that it was melissa hogan’s fault.

every high school had an m. hogan. you know this chick. sh-t, some of you reading might have been this chick. the ultra-mature, ultra intimidating, ultra, ummm, “physically developed at an early age” chick who, by her freshman year was dating seniors and by her senior year was dating steelers.

anyway, m. hogan at lunchtime was basically was responsible for at least 1/4 of my early sexual education (the other 3/4′s being “dream on“, my parents, and “eazy-duz-it”.). our lunch tables were like every other lunch table in every other school in the country, where one or two students tell lascivious (and, in hindsight, completely unbelievable) sexual tales while the rest either laughs, co-signs, or nods along in silent affirmation, despite the fact that no one else had done anything even remotely close to what she was talking about. she’d hold court, and we all were captive listeners, storing every story, taking mental notes with every nugget.

one constant theme of m. hogan’s lunchtime lectures was her utter disdain of “one minute men“. one minute men were the bane of her existence, the iago to her othello, the soap to her southerner, and i made “not being a one minute man” my own personal sexual tenet.

by the time i finally got around to having sex, despite my attractive, yet *insert word that means the exact opposite of “virginal* partner and the lovely “vertical smile” anxiously waiting for me to enter, m. hogan stayed in the back of my mind. forget pleasure, i was a man on a mission…a mission to last. i even positioned myself so that her alarm clock was always in my line of sight.

because our site is pg-13 in theory i won’t get into too many specifics, but lets just say that by the 51 minute mark, i finally decided to climax because i ran out of intentionally non-sexy things to think about (for you laypeople out there, this is a common practice used by young men when trying their hardest not to climax. for example “scrambled eggs”, “mailboxes”, and “that guy on the bus with the giant diabetes foot” all went through my mind at one point that day.)

surprisingly, after she spent a couple weeks at upmc presby allowing herself to heal, my partner let me hit on a pretty consistent basis for the next couple months, but not before a couple phone conversations where i had to convince her that the “hour long chili dog” would never, ever, ever happen again. if so, she had a legal team prepped and ready to sue.

anyway, people of verysmartbrothas.com, how was your first time? was it great, good, underwhelming…or did it have potential legal ramifications similar to mine? (nevermind, don’t answer that second question)

—the champ

234 thoughts on “my first time

  1. First!!!!!!!!!

    A guy who can’t last more than a minute is selfish and should be banned from having sex period. Seriously finishing in one minute is like getting a D in math which is not acceptable. Women need a little more than a minute to have some fun too. On the other hand an hour is way too long. I would imagine a vagina being stroked for that long would start to feel raw and irritated especially if condoms are being used (which I hope)

    • “A guy who can’t last more than a minute is selfish and should be banned from having sex period. Seriously finishing in one minute is like getting a D in math which is not acceptable. Women need a little more than a minute to have some fun too.”

      i think somebody needs a rabbit

    • You might have to take virgins into consideration, i dont think they can help it. Most boys dont realize that sex isnt like masturbation, where you can spew within 5 minutes of erection. Those minute men weren’t taught better because girls just lay under them with a grimace and didn’t say a word. I’d suggest telling him you need a little more attention in order for it to feel good for you. if he disregards it AFTER you say something, THEN he’s a selfish prick.

      For some reason, 3/4ths of the men Ive had sex with always busted within the first minute of me putting “Da Hurt” on them (I don’t know why I just called it Da Hurt. It’s actually named Triumph). They always redeemed themselves the second round, but it just seems to happen a lot.

      • “(I don’t know why I just called it Da Hurt. It’s actually named Triumph)”

        If I was drinking Kool-Aid, my screen would have been sprayed by syrupy goodness.

        Syrupy Goodness sounds X-rated. Or like a stripper name. At a strip club in Tougaloo, Mississippi.

      • “For some reason, 3/4ths of the men Ive had sex with always busted within the first minute of me putting “Da Hurt” on them (I don’t know why I just called it Da Hurt. It’s actually named Triumph). They always redeemed themselves the second round, but it just seems to happen a lot.”

        toke’s comments: the gift that keeps on giving

      • Men who are quick to cum need to make sure that their lady is satisified. If a man is challenged in controling his nut, then maybe he needs to make sure his lady is satisfied. Don’t just roll over and go to sleep.

    • ‘LOL @ Dream On! Martin Tupper! Brilliant show!”

      its the show that taught me about breasts. it’ll always have a special place in my heart

      • I really loved the old movie clips, but his boy Eddie always seemed a little suspect to me (even before he was Professor Oglevee & this was public knowledge.) It’s on DVD you know! Sorry I’m off topic. I have ADD.

        So yeah, my 1st time…:)

    • Indeed. “Dream On” was absolutely some of HBO’s best series television…at least until hype joints like “The Wire” and “Entourage” came along.

      But I never understood how Martin Tupper got all that @$$ as goofy as he looked. Now THAT is an X-File/Unsolved Mystery/Ripley’s Believe It or Not…ok?

    • I also watched Dream On and I remember this one episode very specifically where the woman he was having sex with screwed him like a tiger or rabbit (or some wild animal)…and i remember that reference being a good thing and thinking am i supposed to know how to do that? I was still a virgin at the time and terrified that I may have to fake a seizure in order to capture the essence of that woman’s performance. Anyway, I loved that show too.

    • I can’t speak for the Champ, but NWA definitely provided my initial information on the procurement of ‘dome’.

      “Just Don’t Bite It (She Swallowed It)”

      Classic material.

    • “Did you really use Eazy E as an instructional tool? LOL”

      i used to sneak and listen to that on my parents record player with the headphones on.

      to this day, I still have no idea how i tricked my dad into buying me that album

    • What about Indian Girl (An Adult Story) by Slick Rick?

      I will never forget the day in fifth or sixth grade when someone passed me a walkman and headphones on a bus trip to Hershey Park. I pressed play and sat there with my mouth open for 10 minutes. They actually took a picture of my face. lol

    • Lesson 1, first you grab the d*ck then… and then SPLASH!!! I remember that my mother had to buy that tape for me because it had the Parental Advisory sticker on it, and for some reason she never batted an eye! little did she know.

      Easy E, I’d say that tape was very instructional…and that’s all i have to say on the matter.

  2. My first time was a horrific experience. I was absolutely traumatized by the whole thing, I didn’t attempt sex again for about 18 months after that.

    That one experience also probably cemented my choice/preference/whatnot in men. Thats a comment for another blog, though.

    I was 17. He was 24. It was a horribly painful, bloody mess. I mean bloody literally. I thought he killed me. Granted I already knew there might be some blood the first time. Yeah this was murder scene amounts of blood.

    All of that was probably way too much information, but I felt the need to express just how horrible the whole thing was.

    Y’all have NO IDEA how happy I was to discover that it actually got better and was actually FUN and felt good.

    I hate you Tony Ignacio.

  3. My First Time = Not. So. Memorable. My First Time Being Turned Out By A Woman 7-Years My Senior When I Was 18 = WOW!! Since the site is PG, I won’t go any further.

    I will say that “Eazy Duz It” is one of my most favorite gangsta rap songs of all time. Where else can you find a drunk dude going to pick up his girl, grabbin’ her by her “nappy ass weave”, slappin’ the hoe, and then following up by throwing a right-cross at her father knocking “his old ass out” all in one verse? CLASSIC!! Gangstas these days are too busy lookin’ for “love in the club” and “makin’ it rain” I guess. Damn.

      • I question the thought process of a 25 year old woman ACTUALLY being cool with taking an 18 year old boy’s virginity. PLEASE tell me you lied about your age. Otherwise I gotta wonder what was wrong with that sista.

          • Why does something have to be wrong with her???! Why is it so hard to believe that monk is simply that mack-a-docious?!

            • Go on ahead Monk. Get your splackavellie, on.

              You know the worst part about using the word “splackavellie”?

              I had to sing the song to remember how to spell it.

              My guitar gently weeps.

            • No offense to MONK. He might very well be KANG MACKADOCIOUS, but still! When I was 25, there’s no way I could’ve dated a guy who was 18, let alone done anything else with him. I just couldn’t have that on my record.

        • She didn’t take my virginity, but I will give her the credit for “turning me out” so to say. I’m 31 now and I STILL think about the times we had.

    • my first was a couple years older than me too. i think this is something every guy should experience. i couldnt even imagine how much stranger stuff would have been if we were both virgins

    • I have heard sooo many men esp. black men claim that their first time was by someone significantly older. They were like 13 and the 19 year old babysitter turned them out…What is really going on?

  4. I recall my first time very clearly. I was 18, he was 21. We’d been together for about a year. We had fooled around countless times. And honestly had done just about everything else. We were in my basementn fooling around, the SHAI CD was playing on the radio and this time we just didnt stop. And for a first time, it wasnt bad at all.

    Immediately after, I broke down and cried for about 45 mins. He held me on his lap and kissed my cheeks the whole time. The for no apperant reason at all, I stopped, hopped up and started making us a pizza. He looked at me like I was nuts and said, ‘babe, what was that about?’ I said, ‘I dont know, I think I just needed to mourn my virginity.’

    After that we ate pizza, watched tv, fell asleep and woke up and did it again.

    I think the odd thing was when he left, my best friend called me and in the middle of our conversation she just came out of the blue and said ‘Ohhhhhh Bitch….You Fucked. Didnt you?’ I guess I even sounded a bit more relaxed.

    • “Immediately after, I broke down and cried for about 45 mins. He held me on his lap and kissed my cheeks the whole time. The for no apperant reason at all, I stopped, hopped up and started making us a pizza”

      are you sure your name isn’t “mariah carey”?

    • Must have been good if you got up and cooked afterwards. I feel like if he kissed your cheeks the entire time you cried, he deserved pizza. High five!

      • Making a pizza after sex is like some low budget Jill Scott sh*t. I wish my gal would’ve made me a pizza. Shit I would’ve taken some ramen noodles.

        • “Making a pizza after sex is like some low budget Jill Scott sh*t. I wish my gal would’ve made me a pizza. Shit I would’ve taken some ramen noodles.”

          my chick got me a glass of chocolate milk. it was the best chocolate milk ive ever had

  5. My first first time or the other one.

    It was, in a word, brief. Interrupted. Unfinished?(My little brother came home from school early.) I think you could say that my virginity after that point was technical.

    Wait… You might mean my very first, first time… Also unfinished…

    When I actually did have a significant duration of sexual congress it was……… okay.

    (Note to self: Try not to fall asleep before you hit the “Submit Comment” button)

    • “My first first time or the other one.

      It was, in a word, brief. Interrupted. Unfinished?(My little brother came home from school early.) I think you could say that my virginity after that point was technical.

      Wait… You might mean my very first, first time… Also unfinished…

      When I actually did have a significant duration of sexual congress it was……… okay.”

      lol…i think being ambigious is just in your nature.

  6. My first time was some traumatic and nothing spectacular! I didn’t do it because of “puppy-love”…I did it becuse I was curious of what all the hoopla was about. No one told me my cooty-cat would feel like it was being ripped open and that I would bleed the next day! What part of “feeling good” is that!?!?

    *shreks at the long hope to have forgotten by now memory*

    I didn’t have sex for a WHILE after that shinanagans (sp?)!

  7. Awwee sh*t! Y’all don’t want to know how a true pimp got down on his first time. But I’mma tell you anyway…

    It was the summer of ‘97, my sophomore year of H.S. and I, being the mini-mack that I was, had just “befriended” the captain of the cheerleading team. (*Shout-out to Brooklyn Tech HS*) One day, she came over to my “Palace of Love” aka “The Honeycomb Hideout” aka “my momma’s crib” and my mom, coincidentally, was out of town. I remember Boyz II Men’s “Uhh Ahh” playing in the background. (if you don’t know about this track…get up on it, immediately!!! It will change your life for the better.)

    Here’s a little background info about the 16yr old version of me: (1.) I was a very naive teenager. (2.) My expectation for male/female sexual interaction only included going to 2nd base (and half-way to 3rd base), which I considered an enormous victory because I had actually never really figured out how sex worked exactly. (3.) The concept of me having sex never entered my mind because, as far as I knew, nobody had sex in H.S. (4.) The lower portion of the female anatomy was a complete mystery to me and I was even a little repulsed by its appearance. It just looked so weird to me.

    Anyway, we were lying in my bed ‘necking’ when she just took over. She was experienced (translation: one partner [who also happened to be her 20yr old boyfriend at the time]). Anyway, it was beautiful and far better than I had ever imagine. That was the single longest minute of my life. Unfortunately, as quick as she jumped on she jumped off. She was stricken with cheater’s remorse. Me on the other hand…I was a Sexual God! Granted, I simply laid there and let her do all the work… but, in that brief minute, I still put it down and can’t nobody tell me different.

  8. ok this has nothing to do with our topic, but i had to share. My boss just told us that due to gas prices we can all work from home Tues-Thurs, only making us come into the office on Monday and Friday. I am doing mental cartwheels. Ok. Done.

    • This is the BEST news I’ve heard since…I don’t even know the last time I’ve heard news this good.

      As good as this news is I am still jealous.

  9. I have a story attached to mine, but it is a bit personal. All I will say is, imagine sticking the back end of a sharpie up your nose.

    I got lucky and had a small penis my first time. It still hurt like a motherfucker. I didn’t bleed. He accused me of lying about being a virgin, and I told him not to get mad just because he had a small dick. Good times

      • naw, thats just what it felt like. something hard and unapologetic forcefully paving its way into a narrow passage that up until that day, you truly believed would stretch to fit it. i mean, if it can fit a finger, it can fit a sharpie

      • LAMO @D*stroy… I read too fast, initially I read “nasal” and automatically it translated to ANAL… I had to go back and re read… LMAO

    • “and I told him not to get mad just because he had a small dick”

      you actually said this? wait, who am i talking to…of course you said this, lol

        • LMAO! Jess, telling a man to his face that he has a small d*ck (right after sex) is an offense that rivals Lucifer’s betrayal of God.

          You don’t just throw the words small d*ck around all willy-nilly. I hope you know that that poor dude is probably plagued with all sorts of security issues. I hope your pleased with yourself. ;-)

        • He said, “Your pussy is mad loose. You’re not a virgin.” Uh, your mom?

          He had insecurity issues before we started. His penis and balls together looked like an army tank. He knew. Calling me loose. GTFoutta here.

  10. My first time was brief as a mug too. I had no clue what I was doing (p0rn makes it all look so simple) and I was messing with the el neighborhood ho-cita.

    Such is life. All I know is that when I saw The Wood, its like my entire life flashed before my eyes. Especially the scene where Michael finally cracks Alicia. Good times.

  11. First off let me say D*STROY is absolutely right about that Boyz II Men track! That shit makes babies, for real.

    Now My first time actually happened much later than I usually admit. I was 18 years old and in Air Force Tech school in Biloxi, MS. She was 25 and fine as frog hair. We started kicking it alot and one night we were at the local, “club”, It was really like a community center for the young Airmen that just turned into a club at night for no reason. We were sitting in a booth and talking, and she was getting a little hot and bothered, In my innocence I did not pick up on the signs, but even if I had seen it coming, what was I going to do about it? I couldn’t take her back to my dorm, hell I couldn’t even wear civilian clothes at the time. So there i sat in my BDUs and combat boots, while she was in a bad little miniskirt about to make a puddle on the floor (TMI?). Finally, I guess she couldn’t take it anymore so she jumped up, grabbed my hand, and led me outside. She took me to a little spot around the back of the building, pulled her skirt up and told me to get it. Thank God instincts kicked in and I got to work, pants around my ankles, hat and combat boots still on and it was raining. I would say I lasted about 15 minutes, but it felt like 30. After that I went back to my dorm and smiled for 3 hours. It was a good experience until the next day when she kept blowing my phone up trying to get another dose, which was a complete shock to me because I had no idea what I was working with at the time. I got scared and stopped talking to her, but it was all for the best anyway, I found out later she was married and had 2 kids back wherever she was from. That is how the monster was born though, in the rain, in camo and steel toed combat boots. It set a nice tone for the adventures that followed.

      • If you like that one, wait till I tell you about the time I stroked my pastor’s daughter on a pool table in Japan…..good times!

      • Ugh…men! *rolling eyes* You’ll have daughters one day. Beautiful daughters who will go through a precocious puberty.

        • PREACH!!! men have no idea what its like to raise a female child. My dad did so much dirt he used to tell me (EXPLICITLY) that he would kill me if I ever… He knew he had to pay back for all the “corn that he stole” (its a Guatemalan saying) which is why I never messed with the Latino dudes (dad was too well connected in the Latino community) now the black dudes that is another story. You reap what you sow. YOU REAP WHAT YOU SOW!

        • LOL! Ladies, wait a minute! She was 20 years old, it’s not as if I took advantage of someone’s little teenager. Why do I have to get the eye roll of disgust for that?

          • “…wait till I tell you about the time I stroked my pastor’s daughter on a pool table in Japan…..good times!”

            You get the STRONG eye roll b/c you’re proud of those TACKY experiences. I understand that these encounters warrant respect in Manworld, but what kind of woman would I be if I could read what you wrote and co-sign? Don’t answer that question. I’d be the woman at the community center turned night club if I could co-sign.

            • Listen. If I got a pastors daughter to spread eagle on top of a pool table I’d be proud of that shit too. It’s like getting a die hard gang member to proudly don a garland of flowers and lipstick to walk down the block he grew up on, just for a chance to hold your hand.

            • (one eye sqinting) Ouch! :-) Ok I respect your point of view, but that was a low blow at the end there!

          • @ big buck… Im not rolling my eyes in disgust at you individually, however as a male species, collectively I was agreeing with 2Degreez that you collectively WILL REAP WHAT YOU SOW when your baby girl starts to bud, and I hope she don’t start at 9 like some of my friend’s baby girls.

    • that “first time” made me want some…I have always wanted to be bent over outside in the rain…been in action a long time and have yet to make it rain in the rain…KU(muhfuggin)DOS!

      • Thank you! I thought it was pretty nice too, I wish it had not been my first time though so i would have really appreciated the novelty of doing it in the rain and all that. But since it was the first time, the only thing on my mind was “I can’t believe i am finally getting some, this is…..oh..oh..aaaagh! LOL!

  12. my first time was w/ my first bf exactly 2 weeks before i turned 16. it was frustrating & painful for the most part b/c he was ginormous. after we got past the blood & pain, it actually felt really good for the 10 mins i could take it. i’ve never been w/ a virgin and never want to either!

  13. Well unfortunately I wasn’t that chic, but I was friends with her. I was a virgin until I was 17 and ready to head off to college.

    Lost my virginity in the back of a stretch limo prom night out on the beach…yep I’m a total cliche’ but I wasn’t about to get to FAM and let some random Kappa take my precious jewels…like so many others I know.

    All in all it was a good night, became a freak the next day though and I haven’t stopped since.

    • “became a freak the next day though and I haven’t stopped since.” lolol

      It is like you go from being a good wholesoome girl to be a being a ‘hoesome’ girl…Or so I have heard

      • Yeah well I try to embrace my inner freakdom whenever possible, which doesn’t actually require me to be a hoe…but in Tallahassee, everyone embraced their inner hoe at one point or another.

        …man, those were some good times.

  14. My first time can only be described as Disney meets Tom Clancy/Steven King/CSI(all of them), you know everything was wonderful and happy till he pulled out his weapon of mass destruction and proceeded well keep reading…We were juniors in high school, I was 15 and he was 17, we were high school sweethearts, we had been bf/gf for 9 months, he the co captain of the boy’s basketball team (undefeated champions that year) I the envy of all my high school female counterparts, we were in Love . We would always go and hang out at his best friend’s house. We would chill (make out/fool around/pretend to be doing homework) in the basement on the couch watching cartoons till about 5:30 ,then he would walk me to the bus stop so I could be home before my parents. On this particular day our hormones were in rare form cause before I knew it he had my dress hiked up and my panties were on the floor, when all of a sudden I felt a pain that I can only describe as what an episiotomy (a surgical incision through the perineum made to enlarge the vagina and assist childbirth) must feel like. As a matter of fact you can not convince me that I didn’t hear my flesh actually tear (I am intentionally being graphic so you can understand this pain and share it with others). I remember looking at the tv and seeing that Duck Tales was on (to this day I can’t watch that cartoon without flinching). After what seemed like forever had passed, [dont get me wrong he was as gentle as he could be considering I felt like he had taken a ginsu knife and literally tore me a new one] it was over. We laid there and cuddled, I with tears in my eyes and a lump in my throat. He rose to get the (obligatory) warm wash cloth and returned , his eyes widened as he handed it to me, we were unaware of the BLOODY mess that had been made during our tryst. In a matter of seconds our romantic interlude had turned from romance to a scene out of CSI, where we were doing all we could to hide the evidence. young love….I always think back to my first time with great positivity, so what each time I peed for the next week I felt like I had slid down a razor blade bannister and was made to sit in alcohol, you cant even imagine what it was like to try and walk… I will leave that up to you I still think of it fondly to this day.

  15. There was a cartoon at the Spike & Mike animation festival that depicted a couple’s first time. That cartoon pretty much described my first experience to a tee (except my first time involved a *lot* of booze).

    Lots of poking/prodding/trying to line up the right holes, and then wondering if it got any better. It did. ;)

    • I forgot to mention – it was with a white girl.

      (don’t shoot me, I came back to the tribe shortly thereafter!)

    • “Lots of poking/prodding/trying to line up the right holes, and then wondering if it got any better. It did.”

      you know whats funny, is that i don;t think i really, really started to enjoy sex until after maybe my 5 or 6 time having it. up until then, i was still on my own personal missions and sh-t

  16. CHAMP! First you make me love you when you typed…”the iago to her othello” (*blushing* just using this reference in casual conversation made me tingle) and then you make me second guess that thought with “the soap to her southerner” (MIC CITY, TEXAS checking in and smelling bath-and-bodywork-licious)…and then love you all over again for giving me a new phrase “hour long chili dog” LM(red)AO…(she was tripping for thinking that was a bad thing…gives you longer to try new ish)

    but I digress, first time? *index finger on chin, squinting eyes trying to remember* it was a LONG time ago…my homegirls older brother Jeff Bell…I spent the night at their house…in his room…GREAT equipment…horrible delivery…no foreplay…bad kisser…overall a 6 out of 10 possible points (5 of which are for his BEAUTIFUL cocoa colored d*ck)…it was so FORGETABLE I waited another year (or so) before I tried the whole “sex” thing again…and have been off the wagon EVER SINCE!

    BTW…I WAS, AM, and WILL ALWAYS BE the Melissa Hogan of Skyline Career Development Center (class of 98 baby!)

    • “she was tripping for thinking that was a bad thing…gives you longer to try new ish”

      lol, honestly, i think she might have been comatose for those last 15 minutes

  17. My first time was with the new cute chick that transferred to our school from Arizona. Me being a country boy, I was already enamored by her previous locale, her west coast dialect and the very notion that at the tender age of 15 she had more tits than McGee going on. Anyway, after our “getting to know each other” stage, she informed me that she had experienced “bliss” twice and looked forward to when we would get there. Now the kid was shook, because she just assumed that I was Mr. Loverman (Shabba!…I loved that song), but she couldn’t have been more farther from the truth. I fronted, like me…uh, yeah…sure I’ve done it before (lie), but like most kids who grew up in the 90′s I learned from that surrogate-father we all know…yes, hip-hop. I too didn’t want to fall into the minutemen category and being that she was experienced I figured she would grade me like my high school Spanish teacher – THOROUHLY (lol). Anyway, when that time came me and my best friend (he was getting at her cousin) go over to her uncle’s house (who was a preacher and preaching at his church that night) to kick it and as they say one thing lead to another and it started to happen. Yo, I was soooo nervous that initially I was just trying to do everything right (while jogging my memory of various songs, movies and p0rn to emulate so as to come off like I was chief-boot-knocka) and as time passed…and passed it was getting close to 9pm (around the time when reverend uncle was to be getting back home) and with listening to all the older dudes talk about “coming to fruition” if you will…I notice that hadn’t happened yet and with time closing in on us more anxiety ensued, then my best friend bangs on the door saying her uncle pulled up in the drive way! So we scramble to put clothes on (all the while I tried to figure out how are we going to get out of here) and she let’s my friend in and we hide under the bed until the coast was clear (meaning uncle reverend apparently had some bad Mexican or something and had to relieve himself upon the porcelain thrown) we tip-toed (with Jordan’s in hand) out the back slide door as to not trip the door chime of the front door. So in my afterglow of “becoming a man” and walking back home while telling my homeboy about the experience I remembered that I didn’t even bust! Which was a bit of a downer, but hey…those times after I made sure fruition came.

    Ya know…after reading some of the ladies anecdotes of primordial sexcapades I’ve come to the realization that I’ve never slept with a virgin…

    • @ AKSHONE- *looking both ways not trying to be too obvious “THOROUHLY” thorouGhly (couldn’t help it)

    • Love the story!

      I was with a virgin once, I hated it and will never do it again. It felt like consensual rape, I felt all wrong and dirty afterward. Luckily I don’t have to worry about that much these days because the age range I tend to date doesn’t usually come in the virgin variety.

      • my ruile is NO VIRGINS…I did it once..I told him NO because he wasn’t circumsized (sp?) so this 28 year old man went and got “clipped” just so I would dust him off…after that…I felt obligated…you gotta give the people what they want…after that…it was a WRAP!! When I broke it off with him, he wrote me a 10 page letter with a drawing of tweety bird at the end with a knife (made of the foil from a piece of Big Red gum) stabbed through his heart…fast fwd 10 years…he’s still trying to get the GOODENess!!

        VIRGINS are a BIG responsibilty…if you’re not IN LOVE with the new booty…don’t do it!

        • “When I broke it off with him, he wrote me a 10 page letter with a drawing of tweety bird at the end with a knife (made of the foil from a piece of Big Red gum) stabbed through his heart”

          *speech…less*

          • wow…(brushing imaginary dirt off my shoulder) I thought it would take more to make you speechless…I feel accomplished now…thanks for that ramdom ego stroke CHAMP!

        • D@mn GOODENess!!! The brotha went and got circumcised as an adult! I always heard that was the equivalent to child birth for men. The 10 page letter…any time someone uses cartoon characters from their gleeful youth and uses his home economic skills to create a faux weapon of acute precision to hit home his sorrow over a breakup was SERIOUS! LOL!!!

          • yeah…he still checks in with me occasionally…when he’s between marriages, hack potnas or whatever female co-dependent fuckery he’s got going on…now he’s a PLAYA FROM THE HIMALAYAS and he blames me…for breaking his heart!

            I repeat…VIRGINS ARE A BIG RESPONSIBILITY…JUST SAY NO!

          • LOL @Akshone!!! Yeah that sh*t is really some crazy sh*t. Not to mention that dude was old as hell doing arts and crafts to convey his emotion! What a clown!

            Anyway, He really proved he was ride or die by getting his jammy nipped and tucked! You did him dirty and wrong Goodeness, you did ‘em dirty-wrong!

        • Wow i’m sitting here in shock that a grown man got circumcised so he could get a piece.

          the power of the poontang is unparalled… my goodness.

    • hold up! I didn’t have a crime scene at my first episode… I was developed at a young age and started my period at 10…back then, when you start your period, you go to the OB/GYN to get checked out…forceps much…so when I finally got down with the fresh…I was already “open” and there wasn’t a vampire buffet going on at all…so don’t hang all your virginal expectations on a bloodbath…

      (sidebar) I didn’t realize we were givint ages with our stories…gonna go to my grave with mine cuz all you knee grows were old as hell bustin cherries…and I was…ummm…not…

      • did i block that out…forceps? really? i also started my period at an early age but forceps i don’t recall. i do remember a clamp or something but that did nothing to lessen the pain experienced during my first time. On the other hand there wasn’t a bloodbath either just a spot or two. Maybe you have a point.

  18. My first was the day before my senior year in college, 21 years old…yep, I was a late bloomer…so late I gave it up to someone in a one-night stand.

    I remember the next morning laying there trying to study his face so I could always remember it. When he woke up I had to ask him his last name. 4 years later, I wouldn’t recognize him if I passed him on the street. Sigh.

    • “I remember the next morning laying there trying to study his face so I could always remember it. When he woke up I had to ask him his last name. 4 years later, I wouldn’t recognize him if I passed him on the street. Sigh.”

      this sounds like a story from an AA meeting

  19. I have a girlfriend who is 29 yrs old and is still a virgin with no end in sight. We have all agreed we are going to throw her virginity a farewell party when she finally gets some.

    • One of my sorority sisters died a virgin, she was 22 had just earned her Master’s degree the night she died. Her mom buried her in a wedding dress, it was so sad.

    • I have to ask…is this by choice or does she just not have any takers? Which is a whole other issue if she doesn’t have any takers.

        • Naw, she is a pretty girl. I mean she is a thick girl, but so am I. (although, we are built differently) But I think her lack of confidence is why she doesnt draw men to her very much. But the girl is definately a pretty girl, beautiful face, skin, hair all of that.

          • Wow, S&S…just by the mere fact that you said she lacks confidence, is thick AND pretty let’s me know that it’s gotta be something else. To some kats that’s the perfect storm! Y’all in ATL, too!…wow.

            • yeah, from what you said, she fills all of the qualifications of the perfect jump-off check list

              thick? check
              cute? check
              low-self-esteem? check
              no std’s or baby-daddy drama? check

              her resume is flawless

          • “Naw, she is a pretty girl. I mean she is a thick girl, but so am I. (although, we are built differently) But I think her lack of confidence is why she doesnt draw men to her very much. But the girl is definately a pretty girl, beautiful face, skin, hair all of that.”

            Some body needs to do a translation on this sh*t!

            • ask a dude what she looks like. girls say their friends are pretty and they are miles from attractive. My sister does that all the time with her friends. She will say her friend is cute and she will be built like a basketball.

            • Deviant,
              LOL! You never want to be built like a basketball. Haaa. I just got a kick out of:

              “I mean she is a thick girl, but so am I. (although, we are built differently)”

              That means S&S is cute-thick and her home girl his a hot-@ss-mess-thick.

  20. I was 21 when I had sex for the first time..

    I was very calculating about it, I just decided it was time for me to experience sex. I met a guy who was a gentlemen and very considerate and I knew he was “safe” to experiment with. I read a book that gave tips on preparing for my first time..that book was a lifesaver. I didn’t tell him I was a virgin so he banged it out with no mercy LOL (I had made him wait a year so he had some pent up frustrations..) He was seriously endowed too. But a stomach full of E&J combined with what I gleaned from that book made my first time not too bad, I don’t remember any pain, in fact I was fairly numb. I think I’m going to call up him up one of these days and tell him he was my first, I’ve felt more weird about that now that I’m older.

  21. You know this first-time convo makes me wonder… where is/are the craziest place(s) that y’all have “done it?”

    My top 3:
    1. The Subway (D-train)
    2. The World Trade Center (outside on a relatively secluded bench)– “Gone but not forgotten.”
    3. A NYC pizza shop bathroom

    • ummm….(thinking really hard)

      2008 – in a shadow box at a swinger’s club…

      1999 – in the glass elevator of a hotel…

      1996 – in the walk in fridge at Subway…

      1995 – and you know that curtain that goes around the screen at the movie theater? there is about 3ft of space from curtain to wall back there…(shout out to CINEMARK MOVIES 14)

      • This list is the truth!!!

        The glass elevator really is dope. But I gotta give it up to you for the walk-in fridge at subway. I love subway sandwiches and I love sex… COMBINED! that must be pure bliss!

    • I have only 2 that i count as crazy

      1.On the steps in a school yard, it was night time
      2.Dining room while my mom was in the living room

      • LMAO!!! #2 should be number 1! While you’re mom was in the living room.

        Were the rooms next to eachother? Was she awake?

    • My top 3:

      1. In a dusty outhouse amongst various lawn cutting and shrubbery maintenance devices (don’t ask).

      2. On a Ferris wheel at the state carnival (d@mn that sounds country, lol)

      3. On the highway using cruise control – me driving (pedals) and her steering (wheel)…VERY scary, but she was hott so it was all worth it!

    • 1. Statue of Liberty Park on 4th of July. (Pre 9/11) Its amazing what crowds of people don’t notice

      2. Outside of MIT library/Bank of the Charles River Boston

      3. Driving back from Logan Airport (Boston) to RI

      • oooh I 4got about the bench outside the Scientology Church Headquarters in Boston…that place is so beautiful and romantic especially at night

        • o0o girl u goin ta hell with a gasoline g-string on!! LOL

          but..hey..i cant talk…the stories I could tell..lol

  22. Indeed. “Dream On” was absolutely some of HBO’s best series television…at least until hype joints like “The Wire” and “Entourage” came along.

    But I never understood how Martin Tupper got all that @$$ as goofy as he looked. Now THAT is an X-File/Unsolved Mystery/Ripley’s Believe It or Not…ok?

    • “But I never understood how Martin Tupper got all that @$$ as goofy as he looked. Now THAT is an X-File/Unsolved Mystery/Ripley’s Believe It or Not…ok?”

      yeah, its kind of like how seinfeld would have a different decent looking chick every episode

  23. Wow, first I gotta give up the ‘slow clap’ for BIGBUCK. Hmm…my first time I was 17 years old and it more or less resembled The Champ’s tale except that I was on the receiving end of the 51 minute chili dog. The soundtrack to my debauchery included the first albums of both Boys II Men and Jodeci. The ENTIRE PLAYTIME of both slow sides. I remember very specifically looking at the clock at the other end of my daybed and thinking “when is this agony going to end?” When I think back to my boyfriend at the time whispering in my ear to “relax and loosen up” I wish I had thought of a witty reply like: “well, I’m sorry but this is the first time I’ve had a large penis inside of me.” The cherry was officially popped- 45 minutes post entry and I felt stoned. The best part, my 2 male “play cousins” (do people still say that?) picked me up and congratulated me with kool-aid, hamburger helper and a seat in their “big boy” barcalounger. I felt like one of the guys…except that my evening eventually ended with hours of soaking in epsom salts. I think virgins should use KY jelly, but it would probably still hurt like shit. And unlike the earlier comment where the woman had the sense to abstain for awhile, my silly a$$ kept on doing it because my boyfriend convinced me that it wouldn’t hurt as much if i did it more. man, what a crock…

    • “The soundtrack to my debauchery included the first albums of both Boys II Men and Jodeci. The ENTIRE PLAYTIME of both slow sides”

      wow, lol. who knew the chili dog was ubiquitous?

    • ur play cousins gave u a CUMMING out party. kool-aid, hamburger helper and the big chair. im telling you simple shit makes the best of times. good 1.

  24. lets see..
    my first time I was 15 he was 19. we had been together for 2 months and I had decided I was ready. as we commenced to “getting it in”
    and all the “not so fast”
    I fainted. from the pain. he was so scared he called 911 cause he thought he really injured me..come to find out..he did! my uterus is still tilted slightly ..and that was 10 years ago..thanx N.Ali..kryptonite d*ck having ba*tard!!!!
    aside from being put on punishment I didn’t do it again for aleast another 6 months!

    • dammnnnn. he called 911? that takes balls, after all he was 19 and technically that’s a case for statuatory…well, you know.

    • LOL kryptonite Dick. LOL you fainted. LOL I only laugh because it seems ur ok now but that had to be harrowing with the ambulance cops parents and such. i couldn’t have written a better scene. FUN-E!

    • your uterus is STILL tilted?? between that and the razor blade bannister/alcohol story… i don’t think i’ll ever “get it in”.

      *i feel like crying*

  25. where: central park, nyc
    when: 19 yrs old
    who: boyfriend from high school/college

    needless to say, i am no longer ‘one with nature’…i had mosquito bites every where!

    and to top it off…we got caught by the police…luckily he let us go..after my boyfriend at the time told him who his father was in nyc gov’t..it wouldn’t have looked good for either of us.

    • “needless to say, i am no longer ‘one with nature’…i had mosquito bites every where!”

      outdoor sex is overrated. too many unprotected holes and too many opportunistic critters.

      • outdoor sex is overrated. too many unprotected holes and too many opportunistic critters.

        This could be the funniest sh*t ever!!!!! LMAO! I immediately imagined some rabid woodland creature licking its frothing chops at the prospect of sliding into someone’s bare @ss. Yikes.

        • shit, i’m not even talking about rabbits and squirrels, but spiders and ants and shit. see…i need to go watch nba superstars 2 or something to get this imagery out of my head

  26. @ miss patterson..honey yes called 911!!
    they didn’t ask him his age I’m guessing so he was relieved for that!
    he still is number one on my list after 10 years. that’s a hard act to follow…lol.
    he set the bar wayyyy too high!

    • “he still is number one on my list after 10 years. that’s a hard act to follow…lol.
      he set the bar wayyyy too high!”

      so the ability to induce faints from pain is a turn-on for you?

  27. I just turned 23 and I’m still a virgin. But from reading some of the posts, I see that dealing with us may become burdensome in a sense (i.e., GOODness’ NO VIRGINS POLICY). I’ve had several opportunities in the the past (especially during h.s. and college), but I never meet anyone I want to do it with :(

    I’ve always contemplated if I should tell the next guy I would consider. What do ya’ll think?

    • Lande,

      Much props to you! Honestly…I envy you. I really don’t have many regrets, but I really regret not having waited until I was married to have sex.

      I was my wife’s first partner and I always wished that I had waited too. I have found that sex is exponentially better with someone you are in love with. This epiphany made me realize that the act of sex is far more profound than most of us realize. I am not saying that a strictly phyiscal romp with a random person doesn’t feel good. But, there is something almost spiritual about a man and woman, who are deeply in love, entrusting themselves to one another through intimacy. This type of passion, vulnerability, trust, risk etc should not be taken lightly nor just offered to any joe shmoe. Once you sleep with someone, you can never get your virginity back… so if you do decide to take the plunge, make sure that the guy is deserving. As you can see we all clearly remember our first time but some of the memories would be better off forgotten.

    • I was talking to a girl friend of mine about this topic of “the first time” and I told her how bothered I was that all the women who commented sounded like they had been tortured and yet all of the men had enjoyable albeit embarrassing first times. She told me that her first experience was NOTHING like what you’ve been reading. She explained that it was enjoyable & painless because he really took time with her and her body. I think you should tell anyone you’re considering that you are a virgin because at least they can approach the situation with more consideration and maturity. Just because you’re out of college doesn’t guarantee that the men you might deal with will know how to please you. D*stroy was very much on point with his advice…it’s very mental/emotional and it’s important that you communicate your needs.

  28. …ok it was good at 16 to have my first orgasm with a girl. after that i was chasing that feeling but with women i felt were sexier. success can run but it could never hide from me. suffice it to say i was on a roll every since. quality over quantity. good sex can come in many diff packages and at the end of the day is as much mental as it is physical but when i say quality in the aforementioned statement i meant the external attraction/looks. wayyy past that now and still prefer substance over form, quality over quantity but more like beauty from the inside out.

      • i have found that there is not much that i have ever wanted and could not have. i was selling shoes and people were calling me Al Bundy and one day i looked up at a high rise on a hill and said to myself; if im gonna sell shit why can’t i be in a building like that selling something that costs a lot of money and making a lot of commission. Inside of a year i was in that very building working for Time Warner making big comissions. I was always the guy leading a group of cats in my highschool years to victories with girls or anything else. When we were pillaging, and getting loot I was creating the schemes and the only one with the presence of mind and composure to stay and max out when everyone else paniced and was ready to run. I’m the guy who took 10 dollars and turned it into a case of beer an ounce of jamaican gold a hotel room and 3 girls for three guys. Its nothing that we cant manifest with proper alignment of desire, will, intent and action. seek and ye shall find. in the abundance of water the fool is thirsty. choice is based on awareness so seek wisdom and understanding and you will attract it to yourself. look for secrets and you will find them. too many people focus on the outer when they should search the inner. its the inner that creates the outer. there is nowhere a man goes that the heart and mind haven’t already been. i could go on but i’d have to charge. mind creates reality literally.

  29. Pingback: Very Smart Brothas | ms. masochistic (part 2)

  30. well lemme be the first shameless one to say i lost mine at 14. it was just weird. but then again, im weird. i didnt start masturbating until i turned 19 (yes, *long* after i started having sex, and only after i read about it in a book) and i didnt have orgasms until i started masturbating. to add to the unfortunateness, i havent been able to keep a good sex partner since. *shrug*

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