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First Time Mishaps...

16 Years Ago


Thought I would post something a little fun... i can't be the only one with a story like this... at least i hope not... ::biggrin::

I was 15 the first time I had sex... I was a good little catholic school girl... no clue about any of this stuff... (most of my friends were still virgins or on the brink of turning in their v-card)...

It was a spring day, after school we went back to his house... no one was there. I sit nervously on his bed... he takes off his pants... and i am all ::confused::...

It was soo very tiny... i started to laugh out loud (ok so i was not so nice when i was 15)... I asked him "how is that going to bring me any sense of pleasure...

sadly, i was right... it didn't...

[no subject]

16 Years Ago


::cry:: great topic! ::tongue::

I think I mentioned it here once or twice before, but it fits here as well. And, since I know how all y'all like a good fit, I will give it another go:

For My First Time, I was 26. It was February in Fargo, ND (ya, the one from the movie... ya sure youbetcha!) I worked half-a-day it was blizzard conditions outside, but I knew I had a 3-day weekend that afternoon, and I hoped it would be filled with many much nakedness. So, I stopped for gas and 'supplies' including Everything you need to make a sandwich (condoms and mints= condiments ya!) just in case, and I packed a huge a*s suitcase, large enough to keep me in clothes for a week or more, as if I planned on being in my clothes for more than 15 minutes tops! (more on the suitcase in a minute...)

Then, came the road trip from Fargo ND to Sioux Falls SD, in a blizzard, at night, to get my wick wet, for the first time... I hoped...

Upon arrival (over an hour later than expected) I locked my keys (and the supplies) in my car. I went to find 'our room', she wasn't there. We were to meet at this real classy hotel that had a 5-star restaurant (called Denny's... I think it's French ::biggrin:: ) right next door, so I met her at the restaurant, as she was starving for more than man-meat by the time I had arrived. We ate quickly, then I informed her about my keys.

30 minutes later, freezing and wet (and not in that good way...) she popped the lock on my car with a wire hanger, and we finally made it to the room. I had slyly left a bouquet of roses outside the door, she was touched, but frozen and wet so could only manage a teeth-chattering moment of gratitude once we got indoors.

I'd like to say we tore each other's clothes off and used our combine body-heat and friction and liberal lateral-hip-thrusts to warm us, but that would be too predictably cliche; and this being the First Time Mishaps thread, inappropriate... not to mention, false.

Instead of the Horizontal Mambo, we played Rummy.... ya, the card game. Remember when you were 8 and you played Rummy? ya, that one. Not even Strip Rummy...... it wasn't going good. But, we had also bought some alcohol when she drove us around to local gas stations looking for a wire hanger with which to pop the lock on my car door. So, I tried to keep my eye on the prize. (and, mmmmm, did she have nice prizes under that sweater!! 36Ds I'd guessed...)

We were fed, warmed, and bored within an hour, so it was time for bed. My last hope, since we shared a room with only a single but massive queen-sized bed. While she excused herself to get into her nightgown, the slick sly gentleman in me kicked in, and I went to my suitcase, not for the sex-supplies, but for my very own pillow and blanket I had packed, in case she was uneasy about climbing under the covers next to the likes of me... I had my own little corner of the bed all made up with my own bedding when she emerged from the bathroom in a single-piece knee-length fluffy cotton nightgown and socks. She smiled and turned out the lights so I couldnt see her blush for long.

Score a few more points for me! YAY!

so, roses, gentlemanly gestures, and appropriately inappropriate amounts of alcohol and the stage was set for the disaster to come... the mind was willing, but the body was weak and ill-prepared. There in the dark, she told me that was sweet of me to make my own bed, but wholly unnecessary; we were adults and it was a pretty big bed, it was cold and blustry outside, and she wouldn't mind if I slid under the covers next to her. I was already under there with her by the time she got to 'that was sweet, but...'

We started out by talking about things sexual, where I reiterated the fact that the only things sexual I knew came from porn, that I hadn't even kissed a girl in 5 years or more, and... and she offered a refresher warm-up course on kissing a girl how she liked to be kissed.

OK, that was pretty cool.

and, things started looking up, or perking up as it were. Her n*****s and my c**k were hard and quivering in no time. It was soon decided that we should go only as far as Second Base; my reckoning was a bit foggy, until she started unbuttoning her nightgown. She undid one button, I undid the next, and started practicing those kissing techniques on her sweet warm neck and shoulder. I did my very best to inch the nightgown off her shoulders with my chin and subtle manipulations with my fingers, but to no avail... turns out there were a few more buttons down the front of that nightgown that I had neglected once I had turned my attention to the kissing and groping and fondling...

eventually, she pulled the buttons open herself and climbed her way out of the top of the gown, exposing her breasts to me fully. They were amazing, thanks for the mammaries! I returned the favor and tossed my shirt off over my head. Is it supposed to just tickle the s**t out of ya when you get your n*****s licked and sucked? is that 'the draw' of that particular 'erotic event'?? I dunno... it was lost on me, but I sure enjoyed my turn as Lick/Sucker!

It was getting hot, we were sweating and petting, writhing and grinding; Second Base became more like a try to steal 3rd, when I noticed that she had magically slipped completely out of her nightgown somewhere along the way, and was dry humping my leg (well, not so dry, as it turned out, she was quite aroused!)

We Interrupt the Erotic Disaster for a well-placed a Travel Tip: when planning a road-trip for sex, in blizzard conditions, for a First Time experience, DO NOT WEAR TIGHT JEANS!! ya, so, remember the mind being willing but the body being weak? yep, Li'l Ricky was a mangled mashed mess inside those tight, wet, cold jeans; I was less than half the man I used to be at that critical point in the whole affair. She was naked, wet, perky and panting; I was shrunken, shrivelled and sad, a sorry excuse for a sex-fiend...

after a good while working on the problem, we became frustrated and the mood was gone, or so I thought. Until I heard just 3 little words (no, not THOSE 3!)

"I think I'll take a shower..." she sighed. (ya that's 6 words... WAIT FOR IT!!)

"I think I'll take a shower..." she sighed.
"Oh..." I cried. "OK..." I lied.
"Wanna (1) join (2) me (3)?"

"F**K YA!!!!!!!!!!!!!!!!!!!!!!!!!!!!!" I screamed in my mind, tripping over my sagging, dragging manhood to scramble into the bathroom with her. While the shower heated up, we kissed and cuddled and caressed some life back into me, and I felt, for the first time, FELT her... fuzzy, lumpy womanhood... or woman hood, I guess. I didn't really know what to make of it at the time (come to learn that's called 'the c**t' boys and girls, and it gets 'lumpy' like that if you're really lucky, and she's really aroused... at the time I was hoping it wasn't a 'bad lump' or a left-over from some recent gender-bending surgical procedure, and she seemed to enjoy the touch of my fingertips on that spot, so I kept it there.. stupid stupid boy! it didn't occur to me at the time to move a fingertip's length further south, and get all up in her business... I was such a n00b! after waht felt like hours rubbing her lady-lump (probably 2 or 3 minutes) she took my hand and led me into the shower.

I was throbbing in no time as she washed my front and I washed her back. She made the observation that 'well, since it's all cleaned up now...' and she went down on her knees before me... OMG OMG OMG! if that's what it feels like with a mouth wrapped around it... OMG OMG OMG I can't wait! have to wait... have to... wait... baseball... think about baseball... and Margaret Thatcher naked on a cold day... like today... in tight wet jeans... ooops!

(and not the 'good' oops...) as quickly as it came, it went, without cumming, as it were... I tried to be recipricol with gratitude over her efforts, but I really had no idea and no business going down there without a road-map and a miner's helmet.. to me, that first time, tit-for-twat, was scary and tasted hairy! that's all I recall of my first attempt at giving oral pleasure. OK, that's fine, I'll just do your n*****s, you can do my c**k, fair enough? good! it's hard to be articulate with a mouth full of pubic hair. As Tyler Durdan might say, 'With a c**t in your mouth, you only speak in growls...'

Obviously apparently, I was doing it wrong, that and/or she was not impressed by my lack of staying power... so the shower soon ended before either of us reach our end, and we made our way back to bed, clean and wet and 1/2 the night wasted...

we practiced kissing more, and once I had relaxed and stopped thinking about it so much, I got back to full-on throbbing again eventually. Then, she was concerned about this being my first time, if I could pull out in time, she didnt have any protection herself... so I went to my supplies; I don't know for certain, but I suspect this preparation on my part may have worked against me at this point. Now, I think she thought I thought I was going to be getting some the whole time, when it started out as a simple meet-and-greet type date... regardless, I was informed that in order to use the condom, I would have to get harder...

'It gets harder??' I thought?? HOLY S**T!

well, turns out, after 3 or 4 tries in quick succession, nope, it doesn't get any harder....

...just more difficult!

so, after another good hour or so of wasted effort, and a little more not-so-dry humping against my thigh, she rolled off of me and we went to sleep. She let my soft, mushed, sad little c**k press against her back all night while we cuddled and slept, but I never got any more closer to Victory Lane or Victoria's Secret than that... not that night, not with that woman, any way...

I still call it my First Time though, even though technically, it wasn't.

(oh, and I have gotten much much better at the whole thing since... much much much better! I'll prove it, if I must! dare me? c'mon... any takers?....


...anyone??

Bueller?

Bueller??


s**t!)


((PPS: this whole story is entirely completely 100% fictional... no flacid c***s were injured, no wet p*****s left unfulfilled during the making of this completely fictional account of events that never actually took place... really... I mean it!! why are you laughing!??



s**t

::mad:: )

[no subject]

16 Years Ago


I wasn't a virgin but I was very inexperienced at the time (age 22) in other positions besides missionary (my ex boyfriend was not very good in bed). This was the first time I had ever done it with me on top and I couldn't seem to find a rhythm. So we switched back to missionary and I couldn't help it but burst out crying because I felt so stupid. Luckily my boyfriend was incredibly understanding and was more concerned about why I was crying than my lack of sexual prowess.

Kate

[no subject]

16 Years Ago


Aww, Kate, that sucks! (And not in a good way) Total embarassment!!! Lucky he was such a sweetheart, though!

And RIIIIIIIIIICCCCCCCKKKKKKKKKKKKK!!!!! ::suprised::

You know, the whole time, I'm saying to myself "OK, this is a "first-time" thread. He at LEAST gets LAID!!!"

Nope. Ya didn't.

BUT, at least it wasn't a complete loss... ::drool::



Nicole, Nicole, Nicole, Nicole, Nicole.

Add 2 years to the age (I was 17) and there's MY first time right there. He couldn't even pop the cherry ::sleepy::

[no subject]

16 Years Ago


Um yeah i went home cherry intact... thank GOD it has gotten better over the years or i would probably ended up in the convent or something... haha

[no subject]

16 Years Ago


yep, and I did set the precedent by which I still live today; my girl cums first, and I cum second, or 4th, or 8th... or sometimes not at all...

[no subject]

16 Years Ago


Quote:
Originally posted by Nicole
Um yeah i went home cherry intact... thank GOD it has gotten better over the years or i would probably ended up in the convent or something... haha


I know, right?? That's what I'M saying!!! ::drool::

[no subject]

16 Years Ago


I clung to my virginity, waiting for �Mr. Right� for a lot longer than most of my friends. By the time I was 21, I was very horny and tired of waiting. I had been dating my boyfriend for 3 months and we did everything two sex-crazed lovers can do, except intercourse. He was waiting for me to give him the green light, but I I was waiting for him to initiate. After two more months passed, and no condoms were fastened, it was getting kinda weird. What in the hell were we waiting for? I was determined to make it happen, no matter what, on New Years eve. He & I were going to a dinner party with friends and then returning to his place for the night. It was going to be perfect!
Well, the morning of New Years Eve, I woke up with a bad stomach flu. It was so bad that I couldn�t get out of bed all day. Any light, smell, sounds or touch made me feel worse. But I managed to drag my weary a*s out of bed and go to the party. I couldn�t eat, drink or even carry on a conversation. At midnight, my boyfriend kissed me, but I had to stop him because I was too nauseas.
During the car ride back to his place we started our usual fooling around, which lead to more fooling around in his bedroom. Maybe it was the endorphins, or sheer will, but I actually felt well enough to carry out my mission. I asked him if he had any condoms and he leapt out of bed so fast to get one that I laughed. I didn�t really care about tender words or pleasure; I just wanted to get it over with before I vomited. It wasn't as painful as I had expected, but it wasn't good either.
The next morning my stomach flu was gone. Sexual healing, of course. The first thing I did was check for the tell tale sign of blood on the sheets. Gross, I know, but this is what girls do. I hadn�t told him that I was a virgin and he didn�t act like he knew. I was very relieved and confused to find no trace of blood. Anyway, we had sex 3 times that morning, which set some pretty high expectations for our future sessions. I was pretty disappointed when I learned that sort of stamina wasn't typical for him.
It�s still a mystery as to when my cherry was officially popped. Perhaps it�s still there waiting for Mr. Right � ; )