Old 02-15-2019, 07:28 PM   #1
jackpoll999
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describe your first sex

Describe your first sex
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Old 02-16-2019, 02:38 PM   #2
Son_of_Battles
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Awkward. Cringingly awkward. I knew where to put it thanks to my extensive online research at redtube and other instructional sites, but even that hadn't prepared me. My hands and legs trembled as with fever while I undressed, and as soon as my dick touched pussy, I was scared out of my mind. It felt so warm and soft, caressing me in a way that my hand never could, and with a pleasure I had never before imagined. Shocks of pleasure shot through me instantly and I feared I would cum before I truely began. The next five or so minutes consisted of me awkwardly sawing into her on the floor of her dimly lit living room.

My anxiety and seflcounciousness stole the moments of true pleasure from the experience. Every slow thrust had me on edge as I thought that this was the one that would push me over the edge. In the end, my fear of cumming inside of her and getting her pregnant forced me to stop before finishing.

After finding myself inside the most intimate place of a girl I barely knew, I couldn't even meet her eyes as we both clumsily redressed. On my way back home, I was elated to have hit this milestone in my life, but at the same time let down with how things turned out...how my nervousness had ruined the greatest experience in my life up to that point.
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Old 02-21-2019, 02:43 AM   #3
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Can't be told on LIT.
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Old 05-12-2019, 11:01 PM   #4
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I tried to tell it on lit, they rejected the story.
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Shmily's first story. enjoy


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Old 05-12-2019, 11:10 PM   #5
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Yep. Age comes into play. Too young for Lit.
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Old 05-12-2019, 11:22 PM   #6
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awkward
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Old 05-12-2019, 11:32 PM   #7
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It hurt . . . never wanted to do it again, then it started feeling good. Who knew
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Old 05-14-2019, 03:14 PM   #8
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Way too young for Literotica and wildly enthusiastic. With my best friends older brother on a sleepover.
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Old 05-14-2019, 04:13 PM   #9
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my first sex stuck with me.
even if it hadn't, the clothes sure as hell don't favor me...
and all the bottled hormones and surgery?

why bother?
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Old 05-14-2019, 08:32 PM   #10
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I was a late bloomer, so it met Lit's standards. I recall enjoying it. We're still friends. Beyond that, I don't remember the details.
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Old 05-15-2019, 07:23 PM   #11
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I up-aged myself six months and posted it here, in First Times. We were sweetly clumsy, but got a little better the few times we were together. The last time we made love, she hid herself behind her long dark hair and a white night-gown, and I walked the two miles home. It was cold, so I walked faster, knowing she was warm in her bed. Nearly all of the women I write about now have long, dark hair; it's not hard to know why.
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Old 05-16-2019, 12:44 PM   #12
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I had a hard time getting any girls to go out with me in high school. I was year older than everyone and often when trying to find out if a girl was interested in me they would imply I was too short or ask me questions about what college I wanted to attend. I had no idea if I was even going to go to college so most girls looked down on me both figuratively and literally.

A friend of mine who was in a similar boat, found some local AOL chat rooms that were people looking for cybersex or desceet hook ups. One night I found a woman in her 40s and I was 19 at the time. We ended up chatting a lot. She live about an hour from me and was married. She had been looking for cybersex because her husband could not perform any more, he was twenty years older with health issues.

Eventually talking dirty with me in chat wasn't enough for her so she asked to meet in person. I drove an hour to pick her up after she got out of work. We found a spot out of the way from the main roads in the woods to park my car. Made out for a bit and then she have me a blowjob. I fingered her clumsily but she seemed to enjoy it.

Two weeks later she messaged me and asked me to not make plans on that Saturday. I didn't and she surprised me at my work. She had gotten a room a local motel and we spent the afternoon and evening banging each others brains out. It was wierd at first because I was trying to do things like I had seen in porn or movies but not everything works like that. She kinda became my instructor as well as my lover. Her and I met up regularly like that for almost a year. She let me try every idea that came to me. She even thought of a few I hadn't.

She was the first person to ever show me real erotica not out of a penthouse magazine and actually told me about this site. I don't think she ever posted a story here but she wrote a few and sent them to me. I wrote her a few too that have long been gone to the ether.

We eventually drifted apart but after she lost her husband she found another guy not quite as young as me. He was maybe 10 years younger than her. She actually passed away from cancer not that long ago.
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Old 05-17-2019, 01:03 AM   #13
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Laurel won’t allow me to give you the details, but the other party was a classmate of my sister. She and I shared a love of art, lit, and food.

She had her first book, a kids’ book, published while she was still at high school. I got to contribute several illustrations. (At the time, I wasn’t sure whether I was going to be a writer or an artist.)

To this day, I’m not sure why we ended up going our separate ways. We ran into each other several years later. She invited me over to her place for supper. The meal was great and then we ended up having glorious sex on the floor in front of the fire. I think for a moment or two we both wondered if we should get back together. But we didn’t.
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Old 05-17-2019, 01:11 AM   #14
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Would violate rules.
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Old 05-17-2019, 03:04 AM   #15
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Quote:
Originally Posted by TornConflict View Post
I had a hard time getting any girls to go out with me in high school. I was year older than everyone and often when trying to find out if a girl was interested in me they would imply I was too short or ask me questions about what college I wanted to attend. I had no idea if I was even going to go to college so most girls looked down on me both figuratively and literally.

A friend of mine who was in a similar boat, found some local AOL chat rooms that were people looking for cybersex or desceet hook ups. One night I found a woman in her 40s and I was 19 at the time. We ended up chatting a lot. She live about an hour from me and was married. She had been looking for cybersex because her husband could not perform any more, he was twenty years older with health issues.

Eventually talking dirty with me in chat wasn't enough for her so she asked to meet in person. I drove an hour to pick her up after she got out of work. We found a spot out of the way from the main roads in the woods to park my car. Made out for a bit and then she have me a blowjob. I fingered her clumsily but she seemed to enjoy it.

Two weeks later she messaged me and asked me to not make plans on that Saturday. I didn't and she surprised me at my work. She had gotten a room a local motel and we spent the afternoon and evening banging each others brains out. It was wierd at first because I was trying to do things like I had seen in porn or movies but not everything works like that. She kinda became my instructor as well as my lover. Her and I met up regularly like that for almost a year. She let me try every idea that came to me. She even thought of a few I hadn't.

She was the first person to ever show me real erotica not out of a penthouse magazine and actually told me about this site. I don't think she ever posted a story here but she wrote a few and sent them to me. I wrote her a few too that have long been gone to the ether.

We eventually drifted apart but after she lost her husband she found another guy not quite as young as me. He was maybe 10 years younger than her. She actually passed away from cancer not that long ago.
This is an interesting first time. Thanks for sharing.

Unfortunately, I have to join the many others who are unable to write about the first time due to Lit age constraints. I guess it's not too much to say it was 100% consensual same gender and quite enlightening.
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Old 06-10-2019, 05:13 PM   #16
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...you realize it is entirely possible to describe sex without attaching an age to it, right?

For example, he was the catcher for the baseball team. I, was an idiot. An afternoon of making out and dry humping led to the least romantic words I’ve ever heard, as he gestured towards his nether regions, “You’re going to do something about that, right? Blue balls are painful.” If I had the mental fortitude, self love or condescending voice that I have now, I would have told him to fuck off. Instead, I behaved like society told me I should: I remained quiet, pliant, grimaced through the horrible pain of a fumbling asshat who did not know his way around a woman’s body, and lost my innocence to someone who was not worthy of even a passing thought.

See? No age attached
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Old 06-13-2019, 11:32 AM   #17
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Being on her b'day no 'fudging' is required to meet Lit rules.

(As I say in chapter one of my story "Tableau," Jamie's parents were "loaded," in both senses of the word.)

She was my friend from school, and we both loved airplanes. We hung out together at the little grass-strip airport that Punch and George, my big brother, did odd-jobs for the manager at. Back in the small west Texas town we all grew up in.

Jamie's older brother was more of a parent to her than the two drunken louses passed out on the floor in one of the the fanciest houses in town. But he went off to Stephen F.'s town (Austin) to attend the U, it was 1974, she was 14.

She gradually moved into our house, sleeping in my small bed with me. Her parents having double, or maybe triple vision might have counted heads, but they didn't notice that she wasn't home. My big brother, who was, and is the best brother ever, used his money and his employee discount at the Farm Supply to buy a mattress.

He drove it, and some pine 1x4s home in his piece of crap pickup. Then he moved a couple pieces of furniture and used a hand saw and hammer to build a bed frame in my room. I was 14 and I finally had a sister to go with my three brothers.

That dichotomy between how my 16 year old brother, and her 18 year old brother reacted... The way George cared more for her and me than getting something for himself, oh like working parts and or seat covers for that pickup. It really made me think. Think about the choices people make in life, and what those choices say about the people making them.

Mom likes to quote First Thessalonians (5:21), "Try all things, and hold fast to what is good." Four years later I had already decided that I was not going to let what anyone else thought about anything else keep me from from keeping what was good around me. I tried to be like my friend Eva; she wasn't oblivious. She just thought about things, and then did what was right in her mind without regard for opinion.

It was Jamie's eighteenth birthday; mine had been less than a month before. When my big brother asked what I would like for this milestone birthday, I asked if we could wait a couple weeks and the three of us go together to a tavern for our first legal drinks. George took us to the nicest restaurant in town instead. That's George.

We were just barely eighteen, and not used to drinking. George was driving and being a responsible adult making sure no harm came to us. We, Jamie and I, got shitfaced. George drove us home, and wished us each a happy birthday and many, many more. We went back to our room, drunk off our butts.

***

I woke up just a little bit before dawn. I was naked in Jamie's bed, intertwined with my sister, also naked. My face was coated with dried pussy juice, as was hers. It felt so good, so right. I wish that I could remember exactly what happened, but I can't. The dawn broke and she woke up with me snuggled up against her.

I wondered what her reaction would be. She kissed me gently. We snuggled and then we went down on each other again in the low angle sun light of an early winter morning in the high desert. That was forty two years ago.

Growing up our parents had a plan; I had a better plan; God had a much better plan. It was post Oil Embargo, post Watergate, post Vietnam. The economy was in the toilet. George was staying home until I graduated so they could go and earn some money.

My last semester of high school had just begun. I planned on maneuvering George and Jamie together, she darn near worshiped him, then we could stay together forever. We are together, Jamie, George and I, all these years later. But it was both more complicated and more wonderful than I could have imagined.

God's plan was to include four others Kristin, Punch, Eva and Lillian. And to use our love to bring some other little souls into this world, they are adults now. I write to honor my lovers, all of them.

Love and Kisses

Lisa Ann
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Last edited by CuteSlaveLisa : 06-13-2019 at 05:19 PM.
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Old 06-16-2019, 01:22 AM   #18
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"I am not so big on first times; my two first times sucked. But this is America, the land of the second-chance, and I am an American, and I believe in the second-chance. Since my heritage is mostly Irish... I asked God for a Mulligan, an unscored do-over, twice...

"My second second time was absolutely wonderful. It was right before Christmas, and nobody could have asked for a better Christmas present (than my lover, he) had this wonderful way of really paying attention to how you moved and acted and reacted as he made love to you.

"My first first time it was indescribable, because except for a short sharp pain, it was over before I even knew it began."

From my upcoming untitled story submission. I will edit a link in if it gets published.

aka Jamie

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Old 06-20-2019, 01:56 AM   #19
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My first time? Awkward and desperate.

The first time with my lady? Coming home to a place I'd never been before.
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Old 06-20-2019, 08:43 AM   #20
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Quote:
Originally Posted by Javahead View Post
...The first time with my lady? Coming home to a place I'd never been before.
So, basically you "seen fire raining from the sky," and it was "sweeter than a lulaby?"

Love and Kisses

Lisa Ann
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