How I ended up having anal sex with a girl before PIV (Interracial, Virgins, Long) [m18/f18]

So some disclaimers: this is long and will take a while to get to the sexual stuff. I have changed some superficial details and names to protect identities but otherwise this is a completely true story of my first sexual experiences and how I ended up having anal sex with a girl before I’d had PIV sex. I am not a writer of any description and this is my first attempt at a story so be gentle. Also, be assured that there is no Loch Ness Monster. Look for the break if you want to skip to where things get sexual.

I left high school a virgin. Not just a virgin, but a never been kissed virgin. Girls wouldn’t just turn me down, they seemed to be a bit insulted that I thought I had a chance. I was short, pale, and geeky. I had acne, braces and was painfully shy. I went off to University aged 18 with my acne gone and braces removed. Regardless, I had built up a lot of insecurities about my attractiveness. Girls didn’t seem to be horrified by me anymore but I was still no girl’s fantasy. A solid 5 out of 10. But that was ok, I had long since made peace with the fact that I was no model. My confidence slowly grew from nothing to still almost non-existent but something. I went on a few casual dates and even kissed a couple of girls, but never got any further than that.

Rani was doing another course but we had some overlapping classes and were paired up in one of our labs. We lived near each other and so ended up walking to and from uni together most days. Rani was Hindu and the same age as me when we met (18). She was of Indian decent but born and raised in England. Rani was devastatingly beautiful. To me she was an easy 10. She had long, jet black hair which framed her pretty face. She had kind, warm eyes and a dazzling wide smile. She was 5 foot 3, slim but had curves. She had D cup breasts, which looked especially big on her slim frame. Her stomach was flat and went out to her wide hips and generous, but not large ass. She was gorgeous, and miles out of my league.

We became good friends. She was genuinely, one of the nicest people you are ever likely to meet. Friendly, generous, kind and good to everyone and anyone. She was outgoing and made friends everywhere she went. People adored her. She was a gentle soul and a bit naïve. She saw the best in everyone and was disappointed when people weren’t as nice as she assumed they were, leaving her open to being hurt and let down on many occasions.

Although she was born and raised in England, her parents were from India and had quite traditional values; values that they passed to her. They were against dating and sex before marriage. I would learn that an Indian girl’s reputation is vitally important and for her to have any chance of being set up with a nice boy from a good family, and so she needed to protect her reputation. I was also to learn that most Indian girls do date, they just keep it quiet. Rani had dated a few boys and it had not worked out well. They were all good looking (including one part-time model- I shit you not), tall, muscular and Indian. Trouble was that Rani did not want to have sex before marriage and when they found out that she was serious, they would either break it off or put her under pressure until she broke it off. Her last boyfriend got really pushy and then went full stalker after she broke up with him. She ended up having to involve the police and the whole experience had given her a bit of fright. She decided that dating was a waste of her time and that guys were assholes who only wanted sex. She decided she would wait until she was ready to get married and get set up with a nice Indian boy.

Anyway, although I found her breathtakingly attractive, I was never one to want what I can’t have. I wasn’t in her league, wasn’t her type and she had sworn off men. I became friends with her without expectation or agenda. We became closer and closer over time. She did wonders for my confidence, telling me that I was good looking and any girl would be lucky. She gave me advice on girls but never thought that any of the girls I liked were good enough. We would spend hours just talking and laughing, often into the early hours. She was a good friend and I was good to her too. We looked out for each other and always had a great time together.

When we were on a night out, guys would continuously hit on her. She started telling them I was her boyfriend. They looked at me skeptically but decided that whether or not she was lying, she clearly wasn’t interested. I did get a kick out of the idea of having a hot girlfriend that was knocking back all these good looking guys. Sad I know, but it was a fun.

We had been close friends for over 6 months and become best friends when she kissed me. It came completely out the blue. It had literally never occurred to me that I was anything but her friend. While she was hugging me, she suddenly looked up and kissed me. We talked and she admitted that she had feelings for me. I adored her but had never thought anything would happen. I’d never imagined a romantic relationship beyond guiltily masturbating at home while I thought about her.

We agreed to keeping our relationship secret and I understood that she wasn’t going to have sex before marriage. Of course I wanted to have sex but I was in a romantic relationship with my best friend and the most beautiful girl I had ever seen with my own eyes so I was in heaven.

……………………………………………………………………………………

A full year went by without anything happening beyond kissing and a bit of groping over clothes. We were very much in love. I never asked for or expected anything more physically. One day she came over to mine wearing a relatively low cut top. This was quite unusual for her as she was usually quite conservative in how she dressed. I couldn’t stop looking at her cleavage and she caught me looking. While we were making out she took my hand and placed in on her breast. This was a first for both of us. “Is this ok?” I asked. “Yes. You like?” she asked. “Of course… But I can’t feel much through all your clothes”. It was great but she had a top, a vest and a bra on so her actual breast was well covered. She guided me under her top and vest and then eventually unhooked her bra and let me feel her breast directly. It felt amazing. Her breasts were big, firm and her nipples long and hard. I played with her nipples every way you could imagine. She even let me lick and suck on her tits, as long as I didn’t look. Eventually she went to the bathroom and when she came back and with a slight air of confusion, told me that her underwear was soaking wet. I honestly couldn’t have grinned any wider. I explained why she was so wet and we laughed, talked and cuddled for the rest of the night. That evening was the hottest of my life up to that point by a wide margin.

After that night, things moved relatively quickly. A short time later she let me see her breasts. Honestly, they were breathtaking. They were big, round and pert with small dark brown areolas and nipples. My first real life breasts and they the best I’d ever seen. This was obviously quite a big deal for both of us and she was quite nervous. After, I asked her if she wanted to see anything of mine. “Well… I would quite like to see your bum but…” she trailed off. “But?” I replied. “But I’d really like to see your penis”. I was a bit surprised but quickly agreed. She looked away and I took my penis out. Siting next to her, my cock was out from my jeans but under my t-shirt. She looked back and I asked her if she was sure and she said yes so I lifted my t-shirt up. We both just looked at it. I was rock solid. “You’re hard?” she said. “Well yes, I just saw your boobs and now you’re looking at it so yes, I’m hard”. She sort of nodded in understanding. Then she said “can I touch it?” I managed to gulp out a meek “yes”. She reached out and held it, moving it about and inspecting it.

After she’d had a good look, she slowly started to stroke me. I let out a sigh. She took that as encouragement and firmed her grip and stroked me more confidently. Now, I would like to tell you that she gave me an amazing hand job but that would be a lie. It wasn’t good. She did her best but I was nervous and I guess had gotten a bit used to being touched in a certain way as I was a fairly prolific masturbator. She wasn’t holding it right, either too much yanking or not enough. Her arm started getting sore. All in all it was awkward for both of us. The spontaneous lust that got us to that point dissipated and it became a bit clinical. Eventually, after a lot of instruction, I came. When I did she froze and I blurted out “don’t stop!!” so she immediately restarted but it was too late, my orgasm was ruined. She cleaned herself up and much to my disappointment said “well, we won’t be doing that again”. Thankfully, it wasn’t true.

Soon after she gave it another go and it was better. It kept getting better and better until she was giving me amazing hand jobs. One day she was laying next to me with her top off while she was rubbing my cock. She was grinding her crotch up against me while we made out. I asked if I could rub her. She said yes but over clothes to begin with. She was wearing jeans and as neither of us were getting much from it, she changed into some leggings. Her pussy was radiating so much heat and she starting moaning as I rubbed her. She lost her concentration and stopped rubbing my cock but held on as she started grinding against my hand. Wetness was starting to soak through and her breathing became heavier and moaning louder. She took my hand and put it under her underwear and told me to keep going. Her pussy felt so warm and soaking wet. I found her clit easily which was swollen and her moaning got immediately louder and more intense. I kept on rubbing while her breathing got quicker and shallower until she suddenly gasped and convulsed forward. I tried to keep rubbing but she battered my hand away. She sat there convulsing every few seconds as she was cumming. Then she burst into tears. Between sobs she said “that was amazing”. It was her first orgasm ever. I was a bit confused by the tears but when she calmed down she explained that she wasn’t upset, it was just very intense and she felt a bit overwhelmed but she had loved it.

She realised that I wasn’t finished and told me she wanted to do something special for me. Without explaining she started rubbing me again and then shuffled down so that her head was next to my throbbing hard cock. I thought I knew what was coming and sure enough she opened her mouth and started sucking me. Now unlike my first hand job, this was incredible. I watched as this beautiful Indian girl sucked on my pale white cock. The sight of watching my cock slide in and out of her dark lips was almost too much to take. She looked up at me with her big beautiful brown eyes as she took as much as she could and gripped the rest with her hand. Her mouth was hot and wet and I could feel her tongue moving over the head of my cock. I closed my eyes and felt my orgasm building and knew it was going to be a big one. Assuming that she wasn’t going to let me cum in her mouth, I told her I was getting close so that she could change to just rubbing me with her hand. She kept going. I tightened my muscles to hold back the cum and told her again but louder. She kept going. I went to say it a third time but it was too late, I couldn’t hold it any longer and the first spurt came out into her mouth and to my surprise, she kept going. I stopped holding back and I came harder than I ever had before, spurting over and over into Rani’s mouth. It was the most intensely pleasurable experience I’d ever had. I could feel my cum running down my cock as she struggled to contain my huge load. She started slowing down and then came off my cock. I opened my eyes and saw her grimacing and then spit my cum out onto my stomach. She then got up and I watched her lovely brown tits jiggle as she ran to the bathroom to wash her mouth out. The sight of her face contorted wasn’t the best ending to my first blowjob, but as I lay back covered in saliva and cum, I felt like a king.

Over the coming months, we learned about each other’s bodies. We became experts in making the other cum hard. She didn’t love receiving oral which was a shame because I loved giving it. We watched each other masturbate, which was new for her but she quickly embraced self-pleasure. I came on her tits, ass and face. I found her g spot and eventually made her squirt much to her embarrassment and my delight. We fingered each other’s assholes and found that I came hard with some prostate massage. Not having sex gave us a focus on experimenting and exploring options other than sex and it was time well spent.

We eventually started getting a bit frustrated at not being able to have sex. I was desperate to just fuck her and she seemed equally desperate to be fucked. When rubbing her, if I talked about sticking my cock inside her, fucking her bareback and cumming deep inside her, she would cum extra hard. She loved talking about climbing on me and riding my cock and making me cum inside her. But I didn’t push and despite everything we’d done, she still wanted to wait till she was married before crossing that line.

This went on for a while until one day she had an idea. She had been speaking to a Muslim friend who had told her that she was also waiting till marriage to have sex but her and boyfriend had regular anal sex. Rani told me that she thought this was a good idea. I told her that I thought it was a bit silly and really, at that point being a virgin was just a technicality. But she thought it was a good idea and when the girl of your dreams asks you to fuck her in the ass, you do as you are told. So we fooled around a bit and when we were both horny and worked up, she bent over and arched her back lifting and offering up her brown ass to me. Seeing her naked still gave me a rush but seeing her bent over, wanting me to take her anal virginity was a sight that will have a place at the top of the wank bank forever.

I got behind her hard as a rock. I separated her ass cheeks and like an idiot, I tried to push it in pretty much dry. It wouldn’t go in. It didn’t help that she was tense. I told her to try and relax, which to be fair is easier said than done when someone is trying to stick a dick in your ass for the first time. I realised that a bit of moisture would probably help and so I fingered her ass with a wet finger and then spat on my hand and rubbed it on my cock till it was plenty moist and tried again. At first we had the same problem, but then suddenly with a slight squelch, I slid into her ass. We both sort of froze as I knelt there behind her. I had no more than the head in but it felt amazing. It was so tight, almost uncomfortable. She looked behind her and our eyes met. The sight of this stunningly beautiful Indian girl looking at me with so much lust in her eyes with my cock in her ass is something I will never forget.

I half expected her to tell me to take it out but instead she looked forward and slowly, started to move up and down on my cock. At first I didn’t do anything but then I started to stroke with her and pushed deeper and deeper into her ass until I was balls deep and she was pushing hard up against me, taking every last inch. I had never had PIV sex but kneeling behind her, with my hands on her hips as I stroked in and out of her ass, balls slapping against her, I felt like I’d lost my virginity. I knew I wasn’t going to last long but when she let out a moan, I instantly came hard and was suddenly spurting rope after rope into her tight warm ass. As my orgasm started to subside, I realised we hadn’t agreed that I could cum in her ass and hoped she would be ok that I had. We both slowed down and then stopped. While I was still in her, she asked “did you cum?” I said a hesitant “yes”. Much to my relief she said “good” and came off my cock, letting out only a tiny dribble of cum and trapping most of my load in her ass. She went to the bathroom to clean up and then we lay together talking for hours in each other’s arms.

If you’re interested and made it this far, we did eventually have sex. And yes, it was on our wedding night, like she always wanted. Hope you enjoyed our story.

Source: reddit.com/r/gonewildstories/comments/4u85b1/how_i_ended_up_having_anal_sex_with_a_girl_before