First Time Simon

Edited 05/09/2020

I just fixed some things people pointed out to me. English is my second language, so, even though I can write something that resembles a lot of English language, I'm in a need for an editor.

Simon

Simon Kelly,

I'd told myself as I looked myself in the mirror,

you have two weeks to get rid of your virginity. You are nineteen, and in two weeks, you'll be in boot camp.

You must get rid of your virginity before that. I tried to make it sound like I was confident I could do it in two weeks, but the truth was that the guy I saw in the mirror wasn't the hunk girls wanted.

At five feet six inches, I was short, which was a significant handicap when trying to pick up girls. Though I wasn't fat or skinny, I wasn't an Adonis either. We long-distance runners rarely are. We're the poster boys of sinewy. My body was smooth, what little body hairs I had were all gathered between my legs. I had a vast blond bush covering most of my dick. That bush made my dick seem pitiful.

I knew that my erect cock was a bit above average. Not much, but it still was slightly longer and quite a bit thicker than average, if you believed the internet. But that had not meant much in the locker room. My flaccid dick was much smaller than the other boys' dicks, and they always mocked me about it.

I'd loved to be a shower instead of being a grower.

That'd made High School much less humiliating.

I scratched the back of my neck and decided to trim my pubic hairs, maybe that would make my dick look bigger. Just when I was about to go back to the bathroom, I glanced out of the window and what I saw made my dick twitch. From my room, I had a straight view of the next-door neighbor's backyard. Even though it was ten am, our neighbor, Mrs. Bailey, was already lying on the sunbed, dressed only into a flimsy excuse of a bikini.

Mrs. Bailey was a shockingly beautiful blond with a heart-shaped face and a perfect nose and full, ruby-like lips and deep blue eyes. Despite being in her mid-thirties, she had the voluptuous and fit body of a woman much younger. Her breasts were big and round and juicy. They were so perfect that I'd heard my mother telling dad that they had to be fake.

I didn't care if they were fake or not, Mrs. Bailey and her long legs and round ass and big tits made nightly visits in my bedroom -- at least, in my fantasy world. As she moved on the sunbed, those magnificent tits jiggled. I wrapped my fingers around my rock-hard erection and stroked my cock, watching her spread her legs as if inviting a man between them. I took it as an invitation; as my hand moved back and forth on my shaft, I imagined myself between her legs.

I rammed my cock into her hot pussy. In and out, in and out... Suddenly my cock erupted and shot my hot cum straight on the floor. "Shit," I muttered as I leaned down and picked a dirty sock from the floor. I wiped my hand and dick, and then I glanced out of the window. I felt the heat forming on my cheeks when I found my eyes locked with Mrs. Bailey's blue eyes. For a moment, we looked at each other, then the corners of her lips curled up to a knowing smirk, and she waved at me.

Stupidly, I waved back at her, still having the dirty sock on my hand. My blush got deeper, and I quickly got out of the window. I cleaned the mess I had made, and then I took a shower. I had just dressed when my mother screamed my name.

"What is it?" Cried back.

"Come down! Now!" Mom yelled.

I sighed; usually, I tried not to meet mom during the mornings when she was grumpy. She often had jobs for me, and I had only two weeks' vacation before I'd go to the army, and I wanted to enjoy every minute of them. When I got downstairs, I found my mother talking with Mrs. Bailey, who now was dressed in red, low cut sundress clinging to her upper half.

"Simon, Diana needs man's help on her home," mom said, "you're free, so you can go and help her."

I blinked in confusion, wondering what was happening. Mom hated Mrs. Bailey; she had tolerated her when Mr. Bailey had been alive, but after he had died, mom had made sure we had nothing to do with her. I guess it is because mom's forty-six and looks every bit of her age, and she doesn't want dad being around a hottie like Mrs. Bailey.

"Simon?" Mom said.

"Huh?" I asked.

"Did you hear what I said?"

"Uh, yeah," I said, running my hand through my hair, still baffled why mom would want me to help Mrs. Bailey. "I heard you. Mrs. Bailey needs help, and you volunteered me."

"Good, at least your ears work," mom said, and then she turned to Mrs. Bailey. "Diana, I'll send him to you after breakfast."

Mrs. Bailey smiled at me. "Oh, breakfast is the least I can offer for his help."

"That's good to hear," Mom said, and then she told me to go with Mrs. Robinson.

I followed Mrs. Robinson to her home, where she told me to go and sit on the patio. I needed to wait less than five minutes before she came back carrying a tray. She placed it on the table, sat opposite me, and asked, "Do you drink coffee?"

"Yeah," I said, trying not to stare at her boobs. From close up, they were even bigger than I had thought. Her slowly swaying breasts could only be described as enormous.

Mrs. Bailey gave me a cup of coffee. As I started to eat, she leaned on the table, crossing her arms beneath her breasts. Her dress yawned open, showing a near indecent amount of her round and smooth breasts and the deep canyon between them. When I saw the outline of her nipples was visible through the material of her dress, I realized she wasn't wearing a bra. I felt my cock swell up hard as I snapped my gaze back to her eyes.

There was a mischievous gleam on them as she said, "Do you see something you like?"

"Oh, yes!" I squealed and then blushed. "Sorry."

"Don't be," she said. "I'm flattered that a young stud like you is interested in old hag like me."

"You're a gorgeous MILF!" I declared and again blushed when I realized what I had said. "Sorry."

Mrs. Bailey giggled. "Thank you, stud," she said. "Do you mind if I smoke while you're eating?"

"No," I said.

"This is a filthy habit, I know, but I haven't been able to stop." Mrs. Bailey said, slowly running her tongue over her lips before lighting up her cigarette. I don't really mind smokers, and she made smoking look elegant and sexy.

After I had eaten breakfast, she and I went to the basement. I had to admit it was a mess, looked more like a scrapyard than a basement. Apparently, Mr. Bailey had been a bit of a hoarder. The basement wasn't air-conditioned, and it was hot as hell, and soon I was soaked in sweat. Three hours later, when Mrs. Bailey told me she'd go and make lunch for us, we'd managed to clear less than a third of the basement. I snorted; I'd been working so hard that I had not had a sexual thought in hours.

That had to be some sort of record for a nineteen-year-old boy.

*****

Mrs. Bailey

When I went down to the basement to tell Simon lunch was ready, for a moment, I just stood at the bottom of the stairs admiring him as he worked. The boy was beautiful and sexy. He had woken my body from a long hibernation into which it had fallen after my husband's death. It had been two years and eight months since I'd had sex, and I'd been mourning so hard that I had not even missed having sex.

I couldn't even remember when was the last time I had masturbated. I suspected it had been around the time when Kevin's cancer had become so bad we couldn't have sex anymore. As his body had withered with it had gone my sexual needs. It was as if my body had fallen asleep after Kevin's death.

But now, my body was wide awake again.

And my mind was trying to tell me it was wrong to lust over a boy who was less than half of my forty-two years. That the idea of a forty-something woman dating a nineteen-year-old boy was disgusting. Then I reminded myself of the fact that I'd been nineteen and my late husband thirty-three when we had met. And almost no one had believed our fourteen-year age gap to be disgusting. If it was acceptable for a man to date a younger woman, why couldn't I date a younger man?

Besides, Simon's mother had proudly told me that he had joined the army. If he was old enough to die for the country, then he was old enough to plow my drooling vagina with his hard cock.

As I looked at shirtless Simon working, his shoulders, his arms, clenching and rippling, my pulse quickened, and I felt the raw lust stirring deep within me. The sweat that glistened on the young man's body accented his honed body, and made me think other ways to make him sweat...

"Simon," I said, shaking the lustful thoughts out of my mind. "The lunch is served at the patio. Please, come before it gets cold."

I almost whimpered when he turned around, Simon had the body of a gymnast. His muscles were cut to perfection. My gaze fell to his crotch, and I swallowed when I saw the bulge forming there; he obviously wanted me.

I quickly snapped my eyes up to his face. It didn't really help; he gave me a boyish smile that made my body ache for him, and it took every bit of restraint I possessed not to jump his bones.

I turned around and walked out of the basement, my mind full of dirty images of Simon between my legs, ramming his cock into me like a jackhammer. As I got to the patio, I felt my pussy getting slick and ready. When I sat down at the table, I glanced at his crotch. The bulge in there was quite sizable. At that moment, I decided I would not let Simon out of my home before I'd gotten his cock in me.

Unless he had a girlfriend. I would not lure any man into cheating. I looked at Simon, feeling a bit disappointed that he'd put the shirt on and asked, "I was wondering... do you have a girlfriend?"

"No," Simon said, "the food tastes good. You are a great cook, Mrs. Bailey."

"Thank you," I said. "Why?"

"Huh?"

"Why don't you have a girlfriend? A handsome young man like you should have a girlfriend," I asked.

Simon blushed. "Dunno, I just don't have a girlfriend."

I looked curiously at him. "You can tell me, I'm a Doctor, I'm used to keeping people's secrets. I promise I won't tell anyone."

Simon was poking his food for a while, and then he said, "I don't know how to talk to girls. When they talk to me, I get all sweaty and nervous and intimidated. Then I always say wrong things," biting his lip, he looked into my eyes, "like, you know, with you when I told you that you're a gorgeous MILF."

"Was it an honest opinion?"

"Yeah," the blushing boy said.

"Then it wasn't a wrong thing to say, and I'm flattered that you think so," I said, "maybe you can practice talking to girls with me?"

He swallowed. "You, you, uh, you're even more intimidating than girls! I mean, you're the sexiest woman I know, and I love your tits and... Shit! Uh, sorry..." he glanced at me. "See? I always say shi-stuff like that."

"I believe I'm starting to realize what your problem is. You say what you think, and the girls of your age are offended by that," I gave him a seductive smile. "But women of my age love to hear how sexy they are. Perhaps, you should start dating older women like me?"

"Uh..." he gasped as his eyes widened. "Um, Mrs. Bailey--are you, uh, like, like... coming on to me?"

"Perhaps," I said, "would it disgust you?"

"God, no! I've been jerking off for you... shit."

I giggled. "You've been jerking off thinking me?" I asked, and the crimson faced boy gave me a slight nod. Since he'd been blurting out his thoughts, I decided not to sensor mine. "Oh, knowing that a young stud like you thinks me when masturbating makes me all hot and bothered..." I confessed and pointed at my nipples. They were protruding my tits like two bullets. "As you can see."

"Uh, yeah," Simon said, keeping his eyes on mine.

I burst into laughter. "Simon, feel free to stare at my tits."

"Oh, God," Simon said, bringing his eyes to my tits. "Mrs. Bailey, do you get some sort of perverse pleasure from teasing the young men?"

I blinked in confusion; I had not thought a young man like him would think I'd be teasing him just for kicks. Apparently, I had to be careful and straightforward with him. I got around the table and sat on his lap. I wrapped my right arm around his neck and grabbed him by the wrist with the other hand. I brought his hand to my breast and said, "Does this feel like I'm teasing?"

"No," he weakly whispered, keeping his hand still on my tit.

I felt his hard-on on my ass, and it made me shiver with arousal. "Fondle it," I commanded. Simon gently squeezed my breast, and I gasped at the feel; it had been too long since my breasts had been properly fondled.

"It feels so soft," Simon muttered as he kneaded my breast.

As I pressed my body against his, I felt the sexual energy cocooning us, and I was fast losing my control. I knew we should have gone inside, but it just felt so good to be on a man's lap, feeling his hard body on mine, that I didn't want to move. Not yet.

"Brush your palm over the nipple, don't yet tweak it, just run your palm over it," I guided him, enjoying the attention he gave to my breast. My tits had always been sensitive, but after the breast reduction and lift surgeries, they had become extremely sensitive. There were times when my late husband had given me titty orgasms just by fondling and sucking my tits.

An electric current shot through me when Simon brushed his palm over my nipple. "Good boy," I moaned when he did it again. "Now move to the other tit," I purred, my lips brushing on his ear. Simon did as I asked, and I moaned into his ear as he continued fondling my breast. "Now, baby, gently squeeze my nipple and tweak... Oooh, yess..." I sighed when he began to tweak my stiff nipples. Jolts of pleasure shot through me, and I kept gasping and moaning as Simon groped my tits tweaking my nipples.

Forgetting we were out on the patio; I slid the strap over my shoulder and pulled my tit out of the dress. "Suck my nipple," I commanded him.

*****

Simon

I couldn't believe it! One of the breasts I'd lusted after for a long time was naked before me. For a moment, I admired her big and round tit and the cute, engorged nipple. It was like an inch-long pencil eraser. Then I leaned down and sucked the nipple into my mouth. I rolled the between my teeth and tongue, I sucked and nibbled on it. Mrs. Bailey pressed my head down while my right hand latched back onto her left tit and twisted the nipple roughly, feeling it harden even more.

"Oh, oh, oh, yes," she moaned, and suddenly, Mrs. Bailey stiffened and let out a keening wail, and her body shuddered. She pushed my face off her breast, and then she kissed me hard on the mouth. "Oh, you wonderful boy," she purred after the kiss, "just for that I'm going to give you the best blowjob you've ever had. Let's get to the bedroom."

She got off my lap, grabbed me by the arm, and started to drag me inside. Not that I was resisting, after all, she'd just promised me a blowjob. It would be the best one I'd ever had since it'd be my first BJ. We had barely gotten inside when Mrs. Bailey pushed me against the wall and kissed me hard, pushing into me. I sucked her tongue into my mouth, pleading her to give me more. She continued to sample my lips, passionately, and feverishly. Then she dropped to her knees, and before I knew what was happening, she had freed my cock.

"Oh, my, I love blowing hard cocks," Mrs. Bailey said and licked the tip of my cock, having a lecherous smile on her face. Then she swallowed my cock. My mind went blank, and I slammed my arms on the wall to take support. Mrs. Bailey sucked me like she was starving and hadn't eaten in a week. She was in complete control of me from the moment she hooked her fingers over the base of my cock.

"Oh, God," I moaned when she took my whole dick into her mouth. It felt so-oo good! So-fucking-good!

I didn't last long. I tried to warn Mrs. Bailey that I was going to cum, but it was too late; my cock erupted in her mouth, pumping shot after shot of hot cum down her throat. I felt her hand between my legs and playing with my balls she swallowed every drop of my cum.

"Now, it is time to go to the bedroom," Mrs. Bailey said and kissed the tip of my dick. When we got to her bedroom, she kissed me tenderly, and then she said, "How experienced are you?"

I felt my cheeks going red. "I'm, uh, I'm, I'm... a virgin," I confessed.

Her eyes widened. "Oh," she said and then gave me a bright smile. "Would you want to learn how to make a girl wild?"

"Oh, God, yes!" I said.

"There really isn't much of a trick to it," Mrs. Bailey frowned. "Only three rules, actually. One, pay attention to the girl. Touch her, praise her, fondle and kiss her. Ask her what she likes and what she wants you to do. Most of us need some warming, and if you just think of yourself and what you want, you will disappoint the girl. Two, note her reactions. She'll show you if she likes or doesn't like what you're doing. I'll later explain to you how to interpret a woman in the bed. And the most important rule take your good time. Don't rush things."

"You mean, do it slowly, like we did at the patio?" I asked.

She tilted her head. "What do you mean?"

"I wanted to attack the nipple, tweak it, you know. But you showed me that I needed to fondle the rest of it first and then just brush my palm over the nipple before concentrating on it," I said.

Mrs. Bailey gave me a huge smile. "Exactly like that. It is much like playing a video game. You need to do all the tasks of the level one to get to level two," she explained as she undressed. Off came the dress and panties, and then she was standing before me in all her naked glory.

She was in good shape; she had the body of a dancer. Muscular thighs, long and shapely legs, narrow waist, wide hips, flat, taut stomach, and muscular arms. And then there were those large, round, and firm breasts most women would have paid a lot to have.

God, she was stunningly beautiful!

As I looked at her, I felt my dick getting hard again, and she giggled. "Oh, my, is all that for me?" she asked, looking at my erection.

"Uh, yes," I said, staring at her big and firm breasts, wondering if they were fake like mom had claimed. They looked to be too big and too perfect not to be surgically improved, but they had felt soft in my hand.

Mrs. Bailey stepped forward and slid her hands under the hem of my shirt. She pulled it up, and the next moment I too was naked. Her hands were on my back, and she pulled me against her soft tits. I loved the way she touched me. The kiss was deep and urgent. I had never been kissed like that before. She kissed me like she wanted me right then and there. Then she pulled away and laid down on the bed.

I got beside her, and as we continued kissing, my hands seemed to have their own mind. They started to stroke her all over, from ass to neck and tits. I let my body take over, and, since I made Mrs. Bailey moan, I figured I was doing something right. The making out became hotter by the minute until she grabbed me by the wrist and guided my hand between her legs as she spread them wide open.

"You have to take your time to do all the tasks of this level before entering the next level," she said.

As I stroked her inner thigh, I kissed her like I owned her, and she kissed back. As the kiss deepened, my mind was on my hand. For a while, I stroked her inner thigh, then I slid my hand to her pussy, and she gasped. I could feel her pussy was soaking wet, and I grabbed it. She whimpered, "Not so hard, stud, don't grab the pussy, you're not Trump. Be gentle, stud, treat my pussy with care. And suck my tits and nipples while doing it," she said, and, as I took her taut nipple into my mouth, she started to guide me how to finger her pussy.