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Losing My virginity to Dipti Aunty

Hello everyone. This is Dhruv. I am here with a story that happened a few years ago and one that I still think about all the time. It’s a long one about losing my virginity. But I wouldn’t be doing it justice unless I included all the details. So sit back and enjoy it. To get it out of the way, I’m 5’9, pretty skinny, and have a medium complexion. I have a standard 6-inch tool that’s quite thick. I’m 24 now. This event took place back when I had completed 18 in the summer of 2014. I had just got done with my boards, did pretty well. I was set to head off to college in Delhi. I lived in Mumbai at the time. The day of my departure drew nearer. I spent time kicking about with my friends who were leaving for college abroad, given I would see them rarely moving forward. One day, I got home after having lunch with some friends, and we decided to meet later in the evening and grab some drinks. My parents had different ideas. “It’s Dipti aunty’s birthday tonight, and she’s throwing a party. We’re leaving for her house at 9,” my mom said. I shrugged and whined to no avail. “This is the last time everyone will get to see you until you return for Diwali. You have to come,” they ordered me. I finally obliged, as there was no point in arguing anymore. I decided to get some shut-eye. 9 ‘o clock rolled around, and we were on our way to Bandra. A little about Dipti aunty: she was definitely my favorite aunty in my parents’ friends’ group. At 35, she was younger than the rest of the aunties and uncles and thereby a lot cooler. When we turned 16, she’d always sneak us a drink or two at family parties. She’d always teasingly ask us about our girlfriends and boyfriends. She was fun to be around. She had been married for 12 years and had an 11-year-old son. But damn, she was absolutely gorgeous. I never thought about her sexually, but always found her extremely attractive. She was a Delhi Punjabi. Extremely fair, slim, and had a great rack and ass. I would best describe her appearance as an older, slightly shorter Anushka Sharma. She was about 5’8. With that being said, she was much older than me and was my parents’ friend. My mind at the time was too innocent to ever fantasize about her. Moving on. Mumbai traffic on a Friday night is ridiculous, so everyone was late. We were the first to get there, and Dipti aunty and Anurag uncle, her husband, were still setting up when we reached. I told my parents I had to make a call, and I’d follow them up later. I really just wanted to get a smoke. So, I made my way up after puffing on a Goldflake King and rang the bell. I made it to the building’s party hall and was greeted by a smiling Dipti aunty. “Look who’s here! Mr. All Grown Up! It’s been so long beta, how are you?” she said she came in for a hug. She looked jaw-dropping. She had a dark blue saree on and her hair tied in a bun. Her waist and hip were well exposed and looked ridiculously sexy. Dipti Aunty always hugged us. But this time, it felt like she lingered. It felt a little different. I didn’t think much of it and went on in. She seemed to be in good spirits, by which I mean she was already a little tipsy. A few minutes after we reached, she remembered she’d left some food and chasers downstairs in the apartment. She asked if I could help her get everything up to the hall. I happily obliged. In the elevator on the way down, we were standing really close to each other. She animatedly acted tired and rested her head on my shoulder. “Throwing a party is so much more tiring than it is fun,” she sighed. I had to agree. She was so close to me. Her boobs were lightly resting on my chest, and it felt so hot. But again, I didn’t think much of it and suppressed any straying thoughts I had. We made it to the apartment and collected the food and chasers. Before we headed back down, she whispered, “Hmm, so it seems like someone is old enough to smoke now. I can smell it on you.” I panicked. Was she going to tell my parents? I’d be dead. But to my relief, she pulled out a pack from a kitchen cabinet. She said, “I won’t tell anyone if you won’t.” “Oh yes, absolutely, don’t worry about that aunty, I won’t,” I replied. “Join me in the balcony for a quick smoke?” she asked. This was so cool. I’d never smoked with an aunty before. Dipti Aunty was just so cool. We got in the balcony, and she lit the smoke. We were standing close, our shoulders touching each other. “Ah, college. You’re going to have a blast. All the young hotties are going to be after you. Don’t forget me when you leave,” she joked and leaned further into me, now partially in front of me. “Come on, aunty, how could I possibly,” I replied. “You’re the coolest aunty in the group, you know that,” I responded. “Awww, what a sweetie,” she said and leaned further in and gave me a lingering 3-second kiss on my cheek. She was now almost entirely in front of me and leaning on the balcony rails. Her ass was literally up against my dick. Fuck whatever thoughts I was trying to suppress before. I was getting hard now. She was so incredibly hot. My hormones were raging. That kiss had to have meant something. I wanted her now. The cigarette was nearly done, and I had to think fast before we went back up. What was the most harmless yet sexual thing I could do? I decided to reciprocate and plant a kiss on her cheek. Risky, but I could play it off if she freaked out. So I put one hand on her bare waist and planted a long kiss on her cheeks. She took a deep breath and backed up further into me, slowly grinding her body against mine and dropped the cigarette off the balcony. Fuck! It’s happening. I kept my kiss planted, and she kept moving. This went on for 30 seconds. She slowly turned her face towards mine and kissed me on the lips. We started kissing. Lips only and slowly some tongue. I was in disbelief. How the fuck was this actually happening. Her body was still facing away from mine. I moved my hands along her waist and placed it on her stomach as we continued kissing. Our tongues were inseparable. She was so experienced. About a minute in, I panicked and broke the kiss. “Aunty, is it okay that we’re doing this? Are you okay with this?” I asked. She was quiet for a moment and responded, “Look, I love my husband. I have a family. And they’ll always be the world to me. But I just want to have some fun. As long as you promise that not a soul will ever know about this.” That was fair. And I wanted her too badly to stop now. I stared at her for a second and went back in to kiss her. “Wait, they’ll be expecting us upstairs. We have to make an excuse,” she said. She called her husband and told him that the maid had undercooked the chicken and that she had to fry it again. She also told them we were short on chasers and that she sent me to the store to buy some. He bought it. “Let’s move inside,” she said. She went in, and I followed. We made it to the living room, and she lay down on the sofa. I got on top of her and got back to making out with her. I slowly began to grind my hips against hers, and she began breathing heavily. She broke away the kiss and took my t-shirt off and then stood up to undo her saree. “Fuck, this is going to be a pain to put back on,” she said. A few moments later, she was in nothing but her black bra and panties. I slipped my jeans off and sat upright on the couch. “We don’t have time, let’s hurry,” she said and slid her panties off before unclipping her bra. There she was, in all her glory. Her body looked like an hourglass. She was so slim yet so thick. Her ass protruded from her hips, and her pink nipples looked incredible on her perfectly shaped boobs. Her pussy was covered in short, trimmed hair. I couldn’t believe I was going to have sex with this woman. She got on her knees and pulled my boxers off before jerking my now fully erect dick. Before I could process anything, she swallowed my dick whole, moving up and down as she moved her tongue. My first blowjob. She kept going, and before I knew it, I was going to cum. I pulled her head up and told her I was close. “Oh, no! Not so soon, beta. Let’s move on now.” She got on her feet, and I couldn’t help myself from reaching out and rubbing her clit. She sighed heavily and whispered, “Put it in.” I slowly slipped my index finger inside her. HOLY. FUCKING. SHIT. She was dripping. Now I knew what people meant when they said a woman was wet. I stroked in and out a few times before she said, “That’s enough, let’s do it.” She lay down on the bed and spread her legs. Her pussy was glistening with her juice. The hair was wet. Everything was wet. I looked at her face, and this 35-year-old aunty now looked like a teenager. That look of lust and vulnerability in her eyes. I placed myself over her. This was it. I was going to lose my virginity. She held my dick and guided it towards her hole. She rubbed it at the entrance for a few seconds. It was soaked. Then, she slowly guided it inside. Fuck. Fuck. Fuck. I was entering a woman. This vagina had given birth to a child. Yet, it gripped my cock tight as I slowly pushed in. I dug my face into her neck and slowly started moving in and out. I was in heaven. Sex is something else. She was so wet. And soft. I moved up to kiss her as I moved in and out of her dripping vagina. We were both sweating. She held my head as we kissed and licked each other tongues. I slowly began picking up the pace and started fucking her hard. Just the thought that this 35-year-old mother and I had snuck off to fuck had gotten me close to the edge. She slowly pushed me out, and I glanced down at my dick and her pussy. My dick and her pussy were covered in her cream. “Sit up,” she commanded. She stood up and got on top of me and slowly began lowering herself on my dick. She grabbed my head and kissed me as I slowly slid all the way into her pussy. She broke the kiss to sigh and then slowly began bobbing up and down. The air was now filled with the sounds of her ass slapping against my thighs and my dick sliding in and out of her soaked pussy. Her boobs bounced in front of my face, and I instinctively took her right boob into my mouth. I lightly bit her nipples and licked them. “Oh fuck, keep doing that,” she said. She was struggling to get words out. I had my hands on her ass and squeezed it as she moved up and down. I don’t know what came over me. But I slowly guided my right hand towards her asshole and lightly ran my finger over it. She didn’t seem to mind, so I slowly slipped the finger halfway inside. She looked down at me and murmured, “Hmm, someone’s a kinky boy.” Here I was, an 18-year-old boy with a 35-year-old mother who was riding my dick while my finger was in her ass. I was ready to cum. I pulled her down on my dick. “I’m really close,” I said. “Me too, get on top of me again,” she responded. She lay back down, and I quickly slipped my dick back into her, stroking in and out. I wasted no time and picked up the pace. The wet sounds of me stroking her pussy were such a turn on. “I’m going to cum,” she said and began kissing me. A moment later, her body froze, and she locked her legs around me. Her pussy gripped my dick hard as she began cumming. That was it. I couldn’t hold it any longer. I plowed her faster, and before I knew it, my balls tingled. I pushed all the way in her and shot rope after rope of cum into her pussy. Our lips were still locked, and I let out a few grunts each time I shot into her. My ears were ringing. I couldn’t believe what was happening. I was in an unbelievable amount of pleasure. It almost felt criminal to feel that good. I collapsed on her and dug my face next to hers. I was finished. I breathed heavily as my dick continued to rest inside her. She stroked my hair and placed kisses on my cheek and whispered, “it’s okay, beta, it’s okay.” It was so emotional. I didn’t know it was possible to feel that good. Our sweat mixed as did our juices. We stayed that way for a good 5 minutes before my dick slipped out of her pussy. “That was something else. I haven’t felt that way in years. Thanks, beta,” she said before going in for a kiss. She got up and cleaned the cum on my dick and her pussy with tissues and started getting ready. We freshened up and headed back to the party hall. Only 30 minutes had passed, but it felt like ages. “I’ll go first. You enter 5 minutes later,” she said. In the elevator, we couldn’t stop placing pecks on each other. I was in love. “No one can know about this. It’ll be the end for both of us, beta. Please. No one,” she begged. “Don’t worry aunty, I would never do that to you,” I reassured her. “Arre, what took you so long, Dhruv?” her husband asked as I entered. “The store was shut uncle, I had to walk further to the next one,” I said. Dipti Aunty overheard the conversation nervously. But she soon realized I was on top of my shit and wouldn’t clumsily give away our secret. Little did Anurag uncle know that I just came inside his wife a few minutes earlier. It was such a cool feeling. I felt like a God. For the rest of the party, we kept catching each other’s eyes. She was back to being the mature Indian aunty that she was expected to be. I was so glad that we had this intimate experience to share - one that would bond us together forever. I was awestruck. I wanted to marry her. And have her with me forever. But of course, that was never going to happen. I left Mumbai a week later, and that was the last I saw Dipti aunty for months. I jerked off thinking about our fuck for months to come. To this day, I think about it every day. Dipti Aunty and I had the opportunity to fuck a few more times after that when I used to come home from college for holidays.

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