Earlier this year I had been dating a man for almost two months and had been mulling over whether I should date him exclusively. He was a stoic yet Punjabi man who had amazing posture and had been in Silicon Valley since he was in college, some 20 years ago. We’d been on a few lovely dates and he did a magnificent job of romancing me and idealizing me as the pinnacle of his sexual desire. He, too, was exceptionally masculine, his jawline so prominent that many times after lovemaking I would lay next to him and run the back of my hand across his neck and cheeks.
He had been divorced for three years, with three kids, and put his kids before anything we did. I could tell, however, that his previous marriage was seriously lacking in the sexual department (as mine had too), as each successive time we made love he mentioned that he wanted to love me more the next time. After a particularly fun session, he mentioned to me if I was interested in anal. I had never a cock in my ass, and mentioned that I was worried at how it would feel. He hadn’t had anal either, and reassured me that if I felt comfortable trying that he would make me feel as comfortable possible. I nodded yes, that sounded fine.
I was very nervous. All week long I massaged my asshole with lube in preparation. I got a Brazilian two days before and did some research online and bought a self water-enema kit to clean me out. Several months earlier I had bleached my asshole, and when I looked at it in the mirror I almost psyched myself into bleaching it even more, but decided against it.
When he came over to my house that evening, he brought his backpack in which he carried lube, a number of toys and a bottle of Malbec and I could see in his lustful eyes that he had one thing on his mind: my tight little puckered asshole.
Once we got tipsy he removed his shirt and removed mine. We were making out sensually, feeling his soft lips against mine and our tongues twirling around each others. His aftershave was so masculine that I could feel my pussy swelling up. Within a minute we were both naked, his hard cock pressed against my stomach. He went to his backpack and opened up the lube, which he squeezed all over his cock. I continued making out with him while lathering the lube all over his cock with both hands as if I was pulling a slippery rope. He stroked his cock too, taking the lube on his hands and spreading it all over my tiny tits and massaging my nipples.
He then picked me up, slung me over his shoulder, slapped my ass and walked over to the bed, gently placing me down. He grabbed his backpack and laid out all of the toys at the foot of the bed; anal beads, a butt plug, whipped cream, and the lube. I was softly moaning in anticipation as we got into the 69 position and he started licking my pussy while I stroked his cock.
He rubbed lube all around my ass and gave me a slap on each cheek before squeezing a dollop on my asshole, which dripped down to my pussy. I pushed myself back so that my asshole was inches from his face and he gently tapped my butthole before rubbing his finger tip on it. I could feel myself loosening up, my anus feeling cool air, before he slowly inserted his entire finger and began penetrating back and forth, back and forth. I was feeling like such a hot dirty slut that I grabbed his hand and started licking and sucking on the finger that had just been in my ass.
He rubbed my clit briefly before rolling me over and asking me to get into my favorite yoga pose: the [nidrasana](https://i.pinimg.com/originals/be/f1/4f/bef14ff833dbd04ab21075527682637f.jpg). He helped me put my legs behind my head, and when I was locked into place he spit in my ass and asked me if I was ready. I said yes. He stroked his cock for a few seconds before trying to insert, but couldn’t even remotely inside.
“Sorry, it’s really tight.” I said.
“It’s ok.” He said softly.
He spit in my ass again and plunged his tongue slowly. Again, I could feel my anus loosening up, cooling down. He was kissing my butthole, and when he lifted I could see a trail of spit connecting my ass to his lips. He reached behind him for the anal beads and inserted the first, smallest bead. It plopped in, as did the second bead. He squeezed more lube and moved the beads like a pipe cleaner. The third bead was relatively larger, and as that bead was swallowed he tried pulling it back out to much resistence. I grasped the bed sheets as I watched my asshole skin get tugged forward. I tapped hard and asked for more lube.
He poured more lube all over and pulled all of the anal beads out. He quickly tried to insert his cock but I clenched, afraid of the pain. He grabbed the whipped cream, spraying it on my pussy and licking it up. I was rubbing my engorged clit vigorously, trying everything I could do loosen up my asshole. One last time, he spit in my asshole, rubbed lube all over the butt plug and inserted it with extreme caution and gentleness. The plug got about a third of the way in before I clenched again and tapped out.
“Your butthole is very tight.” He said. “Are you sure you are comfortable with this?”
“I don’t know.” I said, dejected. “Can you try licking me again?”
He did as told, and began lapping my asshole like a dog at it’s water bowl. I tilted my head back in ecstasy, attempting to reach a meditative state so that he could begin to plow my tight asshole. He spit one last time, plunging his tongue in over and over before using his fingers to dilate me.
“OK try now!” I exclaimed.
He quickly lifted up and inserted his cock head. But I clenched again, and he yelped and swiftly pulled out.
“I don’t think this is going to work.” He said. “The only other thing I can think of is amyl nitrate, but I’m not going to make you do that.”
“I’m sorry my butthole is so tight. And I’m sorry I can’t relax enough.” I felt bad and I could feel some tears welling up. I really truly wanted him to have all of my ass that night, but it wasn’t meant to be. We lost the mood, cleaned up, and laid on eachother in bed watching “Eat Pray Love” while I fondled his balls with my hands. After the movie was fell asleep.
We had another lovemaking session after that, but it was rather milquetoast, as I believe the balloon had been burst. Two weeks later we met for coffee and within the next month he had all but disappeared from my life.
Source: reddit.com/r/gonewildstories/comments/i6m9so/mf_my_indian_lover_tried_his_best_but_my_asshole
Really great story! Without doubt extremely erotic and arousing, but I actually found certain aspects a little comedic, and obviously the end extremely bittersweet. I totally enjoy your stories – thanks so much for sharing! ???
Hot. You need someone with experience to take your anal virginity. I volunteer as tribute.
Once I took a FWB ass virginity like nothing. We were so horny and lost in the moment that wasn’t hard at all which I was surprised. While doing she grabbed her dildo and shove in her pussy and I was like whoa! Yazz!. I think the heat of the moment was the best lube.