Hi guys, I am a long time reader of this sub. I have thoroughly enjoyed reading some of the stories here. I was thinking if I have anything that I can share as a give back. Though I had my share of sex life with girlfriends and hookups, almost all of it is filled with predictable and normal course of events. I have no regrets though.
Having said that I can share a couple of stories (can’t predict if it will be two or three) that happened during the few years I spent in Boston after college. My parents got divorced when I was 3. I grew up with my mom my whole life. My dad was in his law school when I was born. He eventually went on to become a lawyer in the new england region.
I grew up in a town in midwest. My mom did her best to raise me with whatever she had as a tax consultant. She sent me to meet my dad during summers some times. I spent a few summers in Boston, the summer before my senior year being the last. As a kid the change of environment felt very different. While we lived in a small house, my dad lived in almost a mansion with swimming pool, gym and sauna. Whenever I visited my dad, he took me to his tennis practice every day, bought me gifts and did his best to bond with me. I had a room in his house that he got cleaned before I visited.
My step mom was very social person and attended lot of parties and hosted some. All the neighborhood MILFs in their late thirties used to show up at our parties. I couldn’t complain. My room was upstairs and if I peeked out of my blinds, I could see all of our back yard. Saturday and Sunday afternoon were my favorites. Some of the neighborhood MILFs would visit our home and my step mom would hang out by the pool. It was a perfect opportunity for me to check them out.
Particularly, the last summer I was there as a kid, I took a binoculars with me. That made the back yard guests outside in my back yard even closer. I felt like such a pervert peeking out of the blinds and checking out the MILFs. During that last summer there weren’t many opportunities though. It was only 5 or 6 times my step mom had a visitor who took a dip and hung out by the pool. There was one person I could see almost always though. It was our neighbor Geeta.
Our neighbors Amit and Geeta were an Indian family. The husband was a professor and the wife was a management consultant. I almost never saw the prof except some times during tennis practice with my dad. My dad introduced Amit and he asked about my preparation for college. The first time I noticed Geeta was when I looked outside my window one Saturday morning. I woke up early and looked around casually from my balcony. I was rewarded with the sight of a lady walking her dog. I quickly jumped inside my room and started perving through my binoculars.
Holy shit! Although I thought she had a cute face and a slender figure during the times I saw her in my house, she looked busty. She was in her sleep wear, cotton shorts and white T-shirt. I knew she ran a lot as I saw her many times running around. Her bare legs were toned and the grey shorts topping them made them more attractive. As she walked her leashed dog, her tits were moving very freely and I had an instant hard on. There were repeat performances, and I was able to see her a number of times that summer.
I moved back to Boston one summer during college for an internship and there were many things to look forwards to this time. First off I had enough experience now and I was not some horny high schooler. I wasn’t seeing anyone at that time and hoped to make most of the break.
I’ll never forget the afternoon that I looked out in my back yard, and I saw Geeta in her bathing suit. She set up a lounge chair, and then I watched her rubbing suntan lotion all over her legs, shoulders, and face. She was talkint o my step om as she spread her legs, bent over, arched her back, and other nice poses.I stared at her ass through the binoculars as she laid on her stomach. The bathing suit fabric was stretched tight over her ass, displaying her two irresistible half-globes. When she turned over, I could see only the slightest protrusion of her tummy. For the most part she had a pretty flat stomach for an older babe, and the suit was pulled tight over her protruding pussy mound.
While adjusting her towel, she managed to lean over. Her tits were on full display and I could see inside the loose top of her suit, to the non-tanned part of her tits, nearly to her nipple. Damn, I’m sure if I were standing right there next to her, I could see her whole tit and nipple! Geeta was the friendliest of the local women with me, sometimes carrying on long conversations when I’d be out in the yard. Actually, she did all the talking, as I didn’t know what to say to any of these women. But she was a friendly woman.
I bumped into Geeta once during the weekend while I saw her running outside. I’ve seen her running in her black spandex shorts before. What an ass! I stared at her ass as I ran behind her for a few seconds. She had put on some weight ever since I saw her last but she still was an attractive MILF. She slowed down to say hi and asked me when I was back and what I was up to. I caught a whiff of her body odor that smelled lavender. Over the course of next two weeks, I took every opportunity to talk to her. She was a very easy person to talk to and it only made it more easier as time passed. We even flirted a couple of times and she caught me check her out once when I grinned as a response. After talking during some breaks, she invited me for a dinner.
“Come on in,” she called. I entered and followed the sound of her voice. She was in her living room on the couch, legs curled up underneath her. She was wearing a halter dress that tied around her neck. The sides of her breasts were deliciously exposed, the way that she was sitting meant that it rode up her legs in an intriguing and enticing way. I tried to tell myself that it was just because it was warm that she had chosen to dress that way, the same reason why I chose to wear shorts.
Despite a mental mantra reminding myself that this was just a friendly get together for pizza and conversation, I could feel my cock stirring.
“Do you want a beer?” Geeta asked. “The pizza should be here soon.”
I nodded, not fully trusting myself to speak.
“Kitchen’s through there,” she said, pointing to the doorway opposite of what I had come in. “Get me one too while you are at it.”
“Sure,” I finally managed to croak out. I wasn’t entirely sure of what was going on. Was she deliberately teasing me? Was she trying to seduce me? Was I being too cautious? Or was I being fairly clueless? All this went through my head as I entered the kitchen, located the fridge, and grabbed two long-necked bottles of beer. It could have been Corona, but my mind was somewhat focused on other things.
As I came back into the living room, it was to see Geeta paying for the pizza. The poor delivery guy could not take his eyes off of her chest, but from the way she was smiling I don’t think she minded the attention.
Geeta paid for the pizza and turned back to see me watching her. “I didn’t pay for these just to have men pretend not to look at them,” she laughed, pressing the pizza box up against the underside of her breasts. “Come on into the kitchen,” she said. “We’ll eat in there.”
She set the pizza down on the table and stretched up to get down a couple of plates down. “Want me to do that?” I asked.
She shook her head, so I sat down and enjoyed the way her dress rode up her legs. I had to admit that she had a fine ass, and the way the dress hugged her body made me a bit glad to be sitting down so I didn’t embarrass myself. I sipped my beer as she turned around to hide the fact that I had been ogling her as much as I had been.
“Like what you see?” she asked with a small chuckle as she placed a plate in front of me.
I nodded and laughed. “Guilty as charged,” I admitted, opening up the pizza box and placing a slice first on her plate then on mine. We didn’t talk for a while after that, both of us intent on demolishing our pizza.
“Now this is they way to celebrate the end of a week,” she sighed, placing the cool bottle of beer against her neck as I reached for a second slice of pizza. “A bit more relaxing then having to go out too,” she admitted. “I might just be getting too old for that kind of thing.”
“You? Come off it,” I said. “You’re not old.”
“You’re very sweet,” Geeta replied. She finished her beer, downing it quickly. “I think I want another one.”
Ever the gentleman, I got up and got her one.
“So I take it you are single now, huh?” she said.
“Huh?” I replied. “Oh, yeah, Sandy moved out last month,” I said.
“That’s too bad,” Geeta replied, though the look in her eye said that she wasn’t sorry at all.
“Was it a bad break-up?”
I shrugged. “There’s rarely ever a good break-up, is there?”
She chuckled ruefully. “Too true. Do you want anymore pizza?” she asked.
“No, I think I’m good.”
“Why don’t we move back into the living room? Its more comfortable than in here,” she suggested as she got up to put the pizza away.
“Mind if I grab another beer?” I asked, already on my way to the fridge.
“Help yourself,” she said with a smile.
As I sat on her couch drinking my beer, I tried to figure out the signals I was getting from her. I still couldn’t decide if she was just being friendly or if there was more to it then that. I thought maybe she was waiting for me to make the first move. As I waited for her, I heard her close the front door. It was starting to get late, and the nights still got cool when the sun went down, so I didn’t think much of it. Then she walked over to be, and sat down straight on my lap, straddling me.
“Oh, it looks like I’ve got your attention,” she said in a breathy whisper.
I tried to work tongue, lips and jaw to make words, but failed utterly.
“Too strong?” Geeta asked. She took my beer away from me then placed both of my hands on her ass. Either she wasn’t wearing panties or she was wearing a thong, because I didn’t feel anything under her dress except for her ass. “I don’t want to be accused of sending mixed signals.” She ground her hips against me, then leaned in and took my earlobe into her mouth. “Am I coming in loud and clear?” she asked.
I think I managed to grunt a reply, but either way my hands squeezing her ass seemed to be all the encouragement she needed. She pulled away from my ear only to kiss me fiercely, her tongue driving between my lips and into my mouth. I felt her tongue circle around mine, and felt her hands on my shoulders as she kissed me. She pushed away slightly, her lips still inches from mine.
“Better,” she breathed huskily. She bent down and traced kisses along my neck.
I slid my hands down along her calves, then back up her legs, pushing her dress up over her ass. “No panties?” I asked.
“I was wondering how long it was going to take you to notice,” she said.
I squeezed her bare ass then gave it a single sharp slap which made her yelp in surprise.
She ground back against me though and kissed me hard on the mouth again, telling me that it wasn’t completely unwelcome.
She then pulled back again, her small nimble hands working at my shorts. She undid the snap and then the zipper, pressing her hand against my cock through my boxers.
“Mmmm,” she moaned. She pushed off of me, sliding down to the floor between my knees. I lifted my ass up as she tugged my shorts and boxers down in a single pull. “Lose the shirt,” she growled as she took my cock in her hand and slowly stroked it.
I was hardly in a position to argue so I pulled it off and tossed it further down the couch from where I was sitting. She ran her fingers down my legs as she positioned her mouth over my cock. She ran the tip of her tongue over the head of my cock and all I could do was roll my eyes back, tug on her hair, and groan my approval. She smiled up at me, and making sure she kept eye contact with me traced kisses down my cock before taking first one ball and then the other into her mouth. She ran her tongue over them and I just held on to her hair loving the feel of her tongue on my balls.
Geeta let them out of her mouth with a pop and asked, “Think you can untie the knot?” Before I had a chance to reply she had taken the head of my cock back into her mouth and I could feel her tongue swirling around the head of it.
I reached down, my fingers fumbling with the knot as she bobbed her head up and down in my lap. I was finally able to work the knot free and let the ties slide down. I ran my hands along her smooth back and then around to her breasts, dragging my nails lightly against her skin. She moaned around my cock and then opened her mouth wider and pushed me deeper into her mouth. She gagged slightly, but seemed determined to take me all they way into her mouth and I wasn’t about to tell her no. I played with her tits, tugging on her nipples as she sucked my cock. She relaxed her throat and worked me deeper and then I felt her tongue slip out to lick against my balls. I groaned my approval and she pulled her head back up and smiled at me.
“You like my big tits, don’t you?” she said then licked my cock from my balls to the tip. “You like playing with my tits while I suck your cock.” She took me back in her mouth and sucked hard on it making me groan my approval. I wasn’t sure how she expected me to answer while she did that to me, but she didn’t seem too interested in conversation. Her sucking took on a certain rhythm and while she didn’t try to get my entire cock in her mouth she did manage to take about half of me on each down stroke and her tongue kept busy swirling around the head of my cock, teasing me and driving me wild.
I rested my hands on her head and warned her that I was about to cum. Rather then stop, she merely pulled her head back some and worked her tongue against the head of my cock as her hand rapidly stroked my wet cock. I tightened my grip in her hair and bucked my hips up into her mouth. I felt her swallow me, holding her lips tight just under the head of my cock. She waited until she was sure that I was finished before releasing my cock. She looked me full in the eyes and licked her lips seductively.
“There better be more where that came from,” she said. She stood up and pulled her dress off, leaving her in just her bare feet. She leaned over and kissed me on the lips gently. “I’m not nearly done with you,” she murmured. “Lose the clothes.”
I was not about to argue with a woman who had just given my a blowjob, so I quickly shed my sandals and finished pulling off my clothes. I followed her into the bedroom where I saw her stretched out lazily on her bed.
“One good turn deserves another, don’t you think?” she asked, spreading her legs wider. Her pussy was mostly shaved, just a small landing strip of hair left over her swollen lips. I knelt on the bed, kissed my way along the back of her knee and up her thigh. She moaned her appreciation, and when my head was close enough ran her fingers through my hair in encouragement. I kissed her stomach as I ran my hands up her body, cupping her full breasts and squeezing them.
“Mmmm,” she moaned. “Quit teasing.”
“Yes ma’am,” I said with a grin that got me swatted on the top of my head. I flicked the tip of my tongue against her pussy lips which made her writhe, and then I pressed my tongue flat against her pussy, grinding my tongue between her legs.
“Oh, that’s it, that’s it,” she cried as I flicked my tongue against her clit, and I could feel her legs tense when I pushed my tongue inside of her pussy.
My hands slid back down her body, caressing her thighs as I worked my tongue in her, and she moaned in frustration when I moved my tongue away to kiss the inside of her thighs.
“You are such a teeaaasse,” she moaned as I suddenly sucked her clit back into my mouth. She put her legs up on my shoulders and held my head in place as I licked and sucked her pussy, and she screamed in ecstasy when I pushed my finger slowly into her, fingering her while my tongue was busy with her clit.
Her thighs squeezed around my head as she came, but I didn’t stop licking her, sending her from one orgasm straight into another, my finger sliding in and out of her hot wet hole as I licked her. Finally, I relented and kissed my way up her body. She grabbed me roughly and pulled me to her in a fierce kiss, her tongue twisting around mine.
My cock was definitely hard again and was pressed between us, resting against her stomach.
“Mmmm,” she sighed. “I know I’m ready to feel that in me,” she said. She pushed me off of her and rolled on to her side. She opened the drawer and pulled out a condom. She looked
at me and shrugged. “No offense,” she said. “But if you want to play…”
I nodded in agreement. We didn’t know each other that well and I appreciated her caution. She opened the condom and slowly rolled it down onto my hard cock. She stroked me slowly a couple of times before getting on to her hands and knees.
“I’ve been acting like such a bitch in heat that you might as well fuck me like one,” she said as she looked back at me with a grin.
I postioned myself behind her and ran the length of my cock against her pussy before pushing the head of my dick against her. She reached one hand back, grabbing my cock and pushing it inside of her. Geeta felt good, beyond good. She pushed back against me, moaning all the while, and twisted her hips slightly which did very interesting things to my cock. I grabbed her by the hips and started fucking her, slow long strokes where my cock nearly escaped her pussy but always ended up with my balls pressed against her.
“Fuck, fuck, fuck,” Geeta said, almost a mantra as I pushed my cock into her. “Come on baby, fuck my pussy.” She pushed her hips back against me harder, making me fuck her faster. I pulled her hair back with one hand, pulling her head back as we fucked.
“Yeah daddy,” Geeta cried. “Fuck my hot wet pussy,” she cried out as I started fucking her faster, pumping my hard dick in and out of her faster and faster. I pulled back on her hair harder as I fucked her, my other hand squeezing her soft full ass.
She screamed as she came, grinding her ass against me as her pussy tightened and convulsed around my cock. She sank down to the bed, my cock still buried in her, and rested her head on the pillow. “God, I needed that,” Geeta sighed, then pushed back against me. “Let me on top of you.”
I slowly pulled out of her and rolled over on to my back. Rather than facing me though, she straddled my waist with her back toward me. She grabbed my cock with one hand and slowly lowered herself down on to me.
“God, I love how you fill me,” Geeta moaned. She sank her pussy down, completely taking my cock into her. She then leaned forward, her hands on my legs and began rocking her body back and forth. It was all I could do just to grab her hips and thrust up into her, watching her ass bounce up and down as she rode my cock.
“Yes, yes, yes,” she cried as she fucked me.
I could feel my balls tighten, could feel myself about to explode. I grabbed her hips harder and growled, “I’m going to cum.”
“Cum in my baby, cum in me,” she repeated, her head thrown back in total lust. She reached a hand down and cupped my balls as she fucked me.
I didn’t need any more encouragement than that and as I pulled her down hard on to my cock I exploded into the condom. I could feel her cum soon after I did, as she kept grinding down on my cock.
Finally she relaxed and lay down against my chest, my hands wrapped around her waist. “God that was good,” she murmured, her head turned into my neck. She left small light kisses on my neck and ran her hands down my thighs. After a while, she rolled off of me, my cock slipping from her.
She sat up, smiling at me as she rolled the condom off of me and disposed of it. I started to get up, but she rested a hand on my chest, pushing me back to the bed. She lay down next to me, her head on my chest, and one of her legs covering both of mine.
“You don’t have anywhere you need to be, do you?” Geeta asked as I ran my hand lightly through her hair.
“Just here,” I replied. “Just here.”
Source: reddit.com/r/gonewildstories/comments/8mdsb8/mfcheatinglonga_summer_of_surprises