When talking to guys on Lush, I almost always get asked if I do anal. And my answer is always "Sort of," because I don't do it often. But that wasn't always the case. There used to be a time where oral and anal were the only sex I would engage in. This is the story of how that all started.

I was sixteen and had been Seth's girlfriend for almost a month. Seth was tall and on the basketball team. He was half white, half Asian, and had a really sexy and exotic look. All of my girlfirends were very jealous when he took me out on a date to Perkins and I had been feeling a lot of pressure from him, and everyone else, since that night.

After our first date, Seth asked me to be his girlfriend and I said yes. We made out in his car and he played with my breasts. On our next date, I gave him a blowjob and by the third, he was trying to go all the way. I let him know that I'm a virgin and somehow that news got back to me at school.

Only my closest friends knew I was a virgin, but I had been feeling like the only cool kid left who still had her V-card. Virginity was for ugly girls and crazies. I felt like everyone was laughing at me. I had even thought about breaking up with Seth over it, but he was sincerely sorry. He only told one of his closest friends that we hadn't fucked yet because I was nervous and that douche bag spread it around.

All the same, our make out sessions often lead to mutual oral, with Seth licking my pussy. On several occasions, he worked a finger into my tight pussy under my hymen, but I always stopped him. I really wanted my first vaginal intercourse to be with someone I loved and I just wasn't there yet.

Seth was also really into anal play. He loved licking his index finger and sliding it in my tight hole while making out and had even licked it a few times. And after going out for a solid month, he was getting really anxious to fuck it. I had made up my mind, if I wanted to keep Seth as my boyfriend, but wasn't ready to go all the way, I was going to have to open up my ass.

I don't know what teens did before Google, but I was able to get answers to all of my questions. Would anal sex hurt? Possibly, but it could be avoided or lessened with the right lube and teaching Seth how to do it. Seth wasn't a virgin, but he'd never done anal before.

I was too shy to buy the lube myself, so I made Seth do it. I didn't want our first time to be in a car, so we both skipped 7th and 8th period to go to my house two hours before my parents would get home. That would make sure we wouldn't be interrupted. And even though we had made out and played with each other so many times, I was still very nervous.

I don't remember what I wore that day, or what Seth wore. But after closing the door, he began to slowly undress me, kissing me softly. I think he knew this was a big deal for me and I really appreciated how respectful he was being. It wouldn't always be this way, but for today it would be.

We had talked about using lots of lube and after we both got undressed, Seth rolled me onto my tummy and raised my ass in the air. Spreading my cheeks, he squirted some lube on my dry asshole and used an index finger to loosten my tight ass. It felt good and he quickly was trying to add his middle finger into the mix, but it hurt.

"Owww!," I squirmed.

"Sorry," Seth apologized as he returned to just one finger. His left hand began to massage my back as he applied more lube and worked his index finger in deep again. After a few more minutes, he slowly slid his middle finger in, too, and it didn't hurt as bad this time. I lay on my belly, breathing deep as he loosened my little ass.

Seth's left hand left my back and I heard the sound of lube squirting.

"Owww! STOP!!!" At my request, Seth pulled out.

"Are you okay?," he asked as he began to rub my shoulders. I didn't say anything, determined to do this. I just nodded my head, yes. He began to rub his dick between my well lubed ass cheeks. He tried again to slide it slowly into my ass and I bit my lip, moaning in pain and he stopped again.

"Get on your knees," Seth suggested. "Maybe that will help." I got on my knees, squeezing my legs together and trying to relax my ass muscles. Seth pressed the lube against my asshole and squeeze more onto it, fingering it into me sloppily. Some of the lube had dripped down around my pussy.

Standing behind me, Seth placed a hand on my lower back and angled his dick against my hole again. I think he was trying to go slow, but he pushed too hard and slipped in deep, fast and hard. I fought the urge to scream or cry, but remained very still.

My ass felt like something had broken. Like the ring around my hole would never close again. Of course it would, instantly in fact once Seth pulled out. But in that moment, I felt like I would never be the same again. I can only imagine that Seth was feeling the exact opposite.

"Ohhh fuck, baby!" He had wanted to do anal for a long time, since he started watching porn, and at seventeen he was now doing it. He slowly slid out, but not all the way, before plunging back in. "Your ass is so fucking tight!"

Seth's hands rested on my shoulders and he began to fuck me. The pain at the base of my ass lessened with each thrust and somwhere deep inside me there was some pleasure. Not enough to get me off, but it wasn't completely without pleasure. I would later learn, after losing my vaginal virginity, that Seth's dick had been massaging my g-spot from behind. But I wasn't yet knowledgeable about that.

"Ohhh Seth!" I moaned from the little bit of pleasure I was getting. But truthfully, my pleasure from that expeirence wasn't just in having his dick inside me. The real pleasure came from being able to please Seth the way he wanted to be. It was a compromise that also fulfilled one of his deep desires. I reached between my legs and rubbed my clit as Seth continued to ride my ass, moaning and squeezing my shoulders.

"Fuck yes!" Seth yelled as he dove his dick in as deep as he could and held it there. I wasn't able to instantly tell that he was cumming, but figured it out quickly. I can feel a dick pulsing and the warmth of cum inside my pussy, but have less sensation in my ass when this happens. Seth pulled out of my ass and my fear that it wouldn't go back to normal was put to rest. It snapped shut so fast that it squeezed the last drops out of his dick.

Afterwards, Seth and I cuddled and made out until it was time for him to go. I took a shower and cleaned the lube off my pussy, rubbing my clit and making myself cum in the process. As Seth and I continued to fuck, we discovered that I could cum too with clit play in addition to his pleasure deep inside my ass. It wasn't too long before I decided I loved Seth enough to give him my pussy, but until then he would fuck my ass almost daily. 

If you liked this story, be sure to let me know. I'll be sharing more of my experiences, as well as some of my fantasies in future posts. Until next time.

XOXO,

Kendall