I could only describe my last year of high school as “rough.” I had been dumped, stood up by my hastily-found prom date, and nearly failed a few classes from grief over my breakup, losing my honors status and my biggest scholarship. I was absolutely thrilled to be moving to another town where I didn’t know a single person.
I couldn’t afford the dorms now that I was sans-scholarship, but I found a small house in a nearby neighborhood that was renting an extra room. As I was moving my things in, I couldn’t help but notice the gorgeous woman next door. She was doing some gardening in the front yard, and I tried not to be too obvious that I was checking her out. I made a point of carrying the biggest, heaviest objects when she was looking, even though I’m kind of a skinny guy.
I was a little disappointed when her husband came out to talk to her, but it’s not like I should have been surprised. Hot, redhead, and busty isn’t the kind of girl who typically finds herself single. The husband drove off after a few minutes, and she went back to her gardening.
As I took out a small chest of drawers, the biggest piece of furniture, she called out, “Hey, muscles!” I looked over, and was surprised to see she was calling me. I gave her a confused look, but she beckoned me with a finger, so I put my drawers down. They slipped just as I was about to put them on the ground.
I went over to her, and she quipped, “I didn’t mean to make you drop your drawers, that sort of thing belongs inside!”
Unsure of what to say, I chuckled a bit nervously and said, “I guess I should get them inside first.” I don’t think I’ll ever know why I said that, but she took pity on me.
“Sorry, I don’t mean to make you uncomfortable. My name is Jenn, I was hoping to ask you for a favor.”
“Sure, what do you need? My name is Terry, by the way.” I wasn’t about to turn down a redhead I’d just met, even if she was married.
“My husband just got called to the other side of the state for work, and we’ve got a bunch of plants being delivered later today. When you’re done moving in, do you think you could come over and give me a hand moving them to the back yard after they’re here?”
I was kind of tired, but again, hot red head was asking. “Yeah, I can do that. I should be ready in a half hour.”
“Great, they’ll be here around two o’clock, so use the extra time to rest. I’d hate for you to wear yourself out before I get you,” she said with a wink.
Maybe she was just a flirt, but she definitely knew how to play with my hormones. I finished my moving and finalized all the arrangements with my new landlady. I took a shower, and spent some time resting like Jenn said, although I couldn’t help but fantasize about her, and the way she winked at me. Soon enough, two o’clock rolled around, and I heard a truck pulling up to the house.
I got up, got dressed, and went to go show off my manliness to the wife next door. As much manliness as a skinny 18-year old has, anyway.
Sure enough, there were some guys unloading a few pallets of flowers onto the driveway. They finished up by the time I had crossed the yard to Jenn’s house. She passed a couple of bills to the guys for their help, and turned to greet me.
“Terry! Thanks for coming over, I really appreciate it!”
“Oh, it’s nothing, really.”
“Don’t be so humble, I’d be hopeless if you weren’t here to help. We need to get these to the back yard so I can plant them.”
I won’t bore you with the details. It was boring, mindless labor, but it wasn’t so bad when I got to check out Jenn’s ass every time she bent over. She was wearing this really sexy choker, too. Afterward, she invited me in to relax.
“You’ve been so nice to me, Terry, can I offer you a beer?”
“I can’t actually drink yet…”
“Oh, come on, you worried your mom will find out? It’ll be fine, you’re an adult!”
I wasn’t about to refuse her twice. I followed her inside, only too excited about having my first beer with a sexy older woman. She lead me to the kitchen, her shapely ass teasing me the whole way, and grabbed a couple of beers from the fridge. She handed them to me, “Hold these, I need to grab a bottle opener.” She bent over to reach into a low drawer, unwittingly giving me a lovely show.
I can’t say I was a fan. It was weirdly bitter, but fizzy like pop, and the combination did not work for me. I could have sipped ram’s piss if it got me to spend time with Jenn, though. We chatted a bit, made small talk, she asked me about my academic goals, the usual things. She got a funny sort of look when she asked about my romantic situation, but I told her about what happened.
“Well, damn, that’s so terrible!” she said after I told her I’d been stood up. She went back to the fridge, “How about another beer?”
“Sure.” I didn’t really want one, but I sure wanted to keep spending time alone with this woman.
“Why don’t we spice it up, you seem like you could use it,” she said with a wink.
I was already feeling a bit of the first beer, and maybe that was what made me say yes, or maybe it was just that I wasn’t sure how to refuse, but I answered, “Why not, I’ll give it the old college try.”
She giggled a little at my awful joke, and grabbed a bottle of whiskey and poured a shot into my second beer. She handed it to me, “Drink up, bud.”
It was definitely stronger, kind of better, too. I started to feel it go to my head kind of quickly.
“Well, it sucks to hear about your scholarship, but I guess I got pretty lucky for it. You were a lifesaver today!”
“And I wouldn’t have had my first beer with a redhead!” I said, turning red when I realized what had come out of my mouth.
She smiled at me, though, “There are worse people to have your first beer with. You never drank with your girlfriend or anything?”
I looked at my feet, “Not really, no. She was always a good girl, we never did anything like that.”
“Did you at least have a little fun with each other?”
“No, she believed in waiting until marriage.”
“So did I, but I still had a reputation for giving great handjobs by the time I went to college.”
“I wish I’d gone to high school with you.”
She laughed a bit, “A lot of guys do, I’m sure, but I think you would have liked me even better in college.” She started slinking toward me a little. My cock was starting to grow a little bit, thinking about what she might have done. “College was where I learned how to suck cock.”
My cock started getting harder, thinking about how Jenn would look on her knees. “I do wish I’d gone to college with you…”
She was right next to me now, and whispered in my ear, “You’re in college now, Terry.” Her hand drifted over my stomach, teasing toward my waistband. “Wouldn’t you like to know what I learned while I was in college?”
Her hand slipped into my pants, and I gasped as I felt her touch. I’d never had anyone else’s hand on my cock before, and it was better than I could have dreamed. Her fingers teased me before wrapping around my shaft.
“If you still think girls should wait until they’re married, I am. My husband won’t be home until tomorrow.”
I moaned out loud as she squeezed my cock just right. “You want to cheat -nnngh!- on him?”
“Oh, honey, I would never! He likes to hear about me playing with other men when he’s not around. He likes it when I stroke their cocks, when I take them in my mouth, but you know what his favorite is?”
“No, what?” I moaned.
“He loves it when I take a boy’s virginity.”
I nearly creamed my jeans right then and there. She could clearly tell I liked the idea, and she slipped down to her knees, unbuttoning my fly and pulling my pants down. “Mmmmm, I can’t believe your girlfriend let a cock like this go to waste.”
“What do you mean?” Was something wrong with my dick? I was starting to get self conscious.
Jenn stroked the length of my shaft, smiling up at me, “This gorgeous, massive, uncut cock.” She licked up the bottom of my shaft, getting a loud, unashamed moan from me. “She didn’t know what she was missing,” she said as she wrapped her lips around the head of my cock, swirling her tongue over it.
“Ooooh, fuck! That feels so good!” She started stroking my shaft as she sucked my head. “I didn’t know I had a big dick. Are you sure?”
She stopped sucking and smiled again as she stroked, her spit letting her fingers glide over the shaft. “It’s so cute that you didn’t know. You never even realized that you were hung like a stallion, and your girlfriend could have been enjoying eight inches of hard cock. It’s a damned shame, really.” She took my cock in her mouth again, this time bobbing up and down.
I leaned back and steadied myself against the kitchen counter, gripping it with my hands. I closed my eyes and enjoyed the work of her lips and tongue. I snapped back to attention when I heard the camera sound from her phone. She had taken a selfie with my cock in her mouth! “What was that?” I asked.
She stopped sucking for a second, typing on her phone. “I’m just texting my husband, letting him know that I’m having fun. I told him you’ve never even had a hand on your cock, he’ll love it.” She went right back to sucking me, and her phone buzzed. She didn’t stop working my cock to check, but when she did, she immediately pushed her way as far down my shaft as she could, driving me crazy as she took another picture while she gagged.
“More for your husband?”
She lifted her head up. “Of course! But you should come upstairs. He says I need to stop teasing and fuck you.”
My heart skipped a beat. I was completely out of my element, and it was unexpected even after she told me implied she wanted my virginity earlier. She turned to walk away, lifting her shirt over her head, and looking over her shoulder at me as she dropped it on the floor and walked up the stairs. I left my pants in the kitchen as I followed her, stripping my shirt, too.
She lead me to her bedroom, and dropped her shorts and panties as soon as she stopped. Bending over, she slipped them slowly, seductively down her legs, knowing I was watching. She turned to face me, bare naked in all her beauty. She smiled deviously at me, “First time you’ve seen a girl naked, stud?”
I was speechless, unable to do more than nod.
She looked down, “You look pretty good yourself. Are you gonna let me play with that monster some more,” she stepped toward me, wrapping her arms around me, “or am I gonna have to beg, sweetie?” She smiled again, pressing her body to mine and grinding her hips on my cock. “You wanna slip that big dick inside me, honey? You wanna feel my pussy on your cock?” she whispered in my ear.
I couldn’t do anything but whimper desperately as she pulled me toward the bed. She smiled that naughty smile as she laid back on the bed, spreading her legs. She reached for my cock, stroking it a few times before she guided it to her pussy. “Go ahead, sexy, take your first pussy!”
I thrust into her, and almost shouted with pleasure. She moaned out loud, “Yes, oh fuck, such a nice, big cock, yes!” I pulled back and thrusted again, getting into a rhythm of fucking, with her moans filling the room as I lost my virginity.
“You’re so deep, don’t stop!”
“Fuck, it feels so good, Jenn!”
“So fucking good!” she said back. Wrapping her arms around me, she pulled me in, bringing her legs back to take me deeper inside her. I drove the entire length of my cock inside her, the two of us panting and grunting with pleasure.
“Oh, fuck, Jenn, I can’t last much longer!”
“Don’t cum yet, sweetie!” She pushed me off of her, much to my surprise.
“What’s wrong? Did I do something bad?”
She smiled and giggled, “Oh, you’re good enough. I might even have to set you up with some of my friends. But we’re not quite finished.” She reached into her nightstand and grabbed a bottle.
“What’s that?”
“Lube, sweetie. My husband insisted that I give you my ass, and I’m a very devoted wife.” She squeezed a little liquid onto her fingers and rubbed it into her ass.
Again, I nearly came as I realized what she meant, and she started rubbing lube onto my cock. I was going to get to try anal the same day I got past first base for the first time!
Jenn turned over and got onto her hands and knees. She spread her legs a little, showing off and presenting her ass to me. “What do you say, sweetie? Are you going to stand there, or are you going to come and stretch my tight little ass?”
I didn’t need encouragement, as I got back on the bed behind her. She kept looking back at me, like there was nothing she wanted more in the world than to get fucked. I took my cock in my hand, pressing it to her second hole.
“Mmmm, come on, sweetie, don’t make me wait. Give me that cock. Stop teasing me an- aahh! Thank you!”
I slid my cock inside her, slowly at first like I had read you should. She was so tight, and the whole act felt wrong, and that just made it so much better.
“Oooh, yeah, how does it feel to be in my ass?” she moaned.
“It feels so good,” I answered.
“Are you gonna keep playing around, or are you gonna fuck my ass and fill me up with that big cock?”
I hadn’t said no to her yet, and this was not the time to start. I pushed me cock inside, and she moaned with every inch as I penetrated her. As I pushed the last inch inside her, I felt her squeezing me with her muscles, teasing me. I pulled back, and thrust inside her again, and again, and again, a little faster each time.
I couldn’t help myself, though, and I lost my patience pretty soon, and started fucking her relentlessly, pounding her tight, firm ass with quick, rough strokes. Her voice filled the room as she begged: “Harder! Deeper! Give me that cock, I love it!”
I felt myself getting close to an orgasm, “Oh, fuck, I think I’m gonna cum!”
Jenn grabbed her phone again, and I thought I could see her taking another selfie. “Do it, baby, do it! Cum for me! Cum in my ass! Fill me up with your cum!”
With encouragement like that, I lost control completely, as I went over the edge, my cock spasming inside her, shooting my cum in her ass. “Fuck, I’m cumming! I’m cumming!”
“Yeah, cum for me! Fuck, yes, give me your cum! Aaaah, yeeessss!!”
As I came down from my climax, I noticed her sending a video of us as I was cumming. “My husband is gonna love this.” My cum dripped from her ass as she took a picture of it to send to her husband. When it was done, she looked up at me.
“I can’t believe you’re still hard! I remember being that age, when guys could keep going and going… Why don’t you take a quick shower, then you can feed my nostalgia?” She asked with a wink.
As always, I obliged, hardly realizing I would spend my first night in a new town fucking the neighbor’s wife.
Source: reddit.com/r/sexystories/comments/5moc20/the_importance_of_being_a_good_neighbor_str8_fm
Wow
Every teenage boy’s dream.