Many readers have been asking me about all
the sexual things I do. Normal things like oral sex, and also the more
extreme things like anal sex. Most readers were disappointed when I told
them that anal sex isn’t really my cup of tea. I do have anal sex, but
only because my partner Edwin loves it so much. So like once a month I
let him have his way and we have anal sex. Though that I don’t enjoy it
as much as normal sex, it does give him a kick. After many requests on
the matter, I decided to write down the story about my first anal
It all happened when I was 20 years old and had a boyfriend named Harald. We had a very serious relationship at that moment and we loved each other very much. He taught me many new things about sex and, in particular, how to really enjoy the art of making love. Before him it was more about pure lust and sex, but he taught me how to make love to each other.
One evening we were lying in bed, hugging and kissing, talking about how much love there was in our relationship. Like always he was wearing a boxer shorts in bed. He always slept wearing those, winter or summer didn’t matter to him. Me on the other hand, though the spring had just started, was wearing an old pajama. I crawled on top of him, one leg on each side of him and we started kissing. His lips parted and so did mine, our tongues started to swirl around in our mouths. I could feel his cock hardening inside his boxers as I slowly ground over it with my crotch.
“Sweetie, that pajama isn’t really helping the mood.“ he said breaking off the kiss.
“But its cold!“ I pouted.
He smiled and the only thing I could do was remove it (or else there wasn’t going to be any sex) and I really was in the mood for some good shagging. I rolled off him and slipped my pajama pants off. Slowly, I unbuttoned the pajama blouse and dropped it on the floor with the pants. I wasn’t wearing a bra underneath and my nipples instantly hardened. While I undressed myself, Harald was slowly rubbing his shaft keeping it hard.
I removed his hand out off his boxers and crawled back on top of him. I positioned myself back on his cock and slowly started to grind it again. With one hand I gently tilted his head aside and starting kissing his neck. He loved it when I did that to him - always did the trick to get him hard as rock. I kissed his neck all over while I kept grinding up and down on his shaft through the fabric of his boxers. My mouth moved downwards and I licked his nipples and made them hard. I followed his happy trail till my lips where right above his crotch. Slowly I took the edges of his boxers and slipped it off.
His penis was standing up, waiting to be sucked between my willing lips. With my hand I grabbed his shaft and tilted it aside so I had a better access to his balls. My tongue started lapping his balls with long wet strokes. Harald started moaning softly. I knew he loved to have his balls licked so I eagerly gave them a nice lapping. His balls were becoming very wet from the licking of my tongue. Very gently I took one in my mouth and sucked on it with care, not trying to hurt him. My hand was sliding easily up and down his shaft while I was enjoying myself with his balls. Sometimes I even moved my tongue all over the area covering from his balls to his anus. But I didn’t go any further.
I wrapped my lips around his shaft and placed sweet kisses all over it. With a firm grip at the bottom of his shaft I took a hold of it. The tip of my tongue moved over the head of his cock as I pulled his foreskin back. This made him moan a little louder. I wrapped my lips and around his cock and let it slip into my mouth as my tongue kept running over the head of his hard penis. With a slow pace I started moving my head up and down as my hand followed the rhythm. Slowly but steady my lips and tongue were making his cock more and more wet. Harald loved it when I took his cock as deep as I could, but I wasn’t really good at deepthroating (I’m still not as good at it as I’d like to be). I always did my best and tried to take as much as I could. Inch by inch, stroke by stroke, I moved my lips closer and closer to the base of his penis. But only an inch or two away, I always started to gag. Harald loved the sound of my gagging on his cock and it made him even hornier.
He laid a hand at the back of my head and decided the pace of my sucking. My lips around his shaft and my hand at the base moved along with my head as I was giving him a nice mouthfucking. He told me to remove my hands away from his penis and grabbed my head with both his hands. With slow bucks up and down he started to fuck my mouth. At first he was moving his cock just an inch or two inside my mouth, but the longer he was fucking me, the deeper he moved it in till I reached my gagging point. He really got turned on by the sounds I made when I gagged and this caused him to move even faster and deeper.
We did this for a few minutes till we decided to move on to the next point. I wanted to feel his mouth so bad on my cunt. I wanted to feel his tongue running up and down my slit. But Harald wasn’t really in the mood for it. I moved my hand into my thong and noticed that I was soaking wet. Quickly I rolled off him and took my thong off.
As I was lying naked on the bed, I spread my legs for him. Harald positioned himself between my legs and with the point of his tongue he flicked over my clit. This felt like electricity going through my body. I arched my back as he grabbed my thighs and quickly lapped up some juices by running his tongue from the base to the top of my vagina. He wasn’t really in the mood for oral sex and quickly moved up to position himself between my legs.
He took his shaft in his hand and slid the head of his cock up and down between the lips of my pussy. A few times he flicked it over my clitoris. I wanted to feel him inside me so badly. He placed the head of his cock against my pussy and slowly guided it into my cunt. His cockhead spread my lips and slowly moved deeper into my wet cunt. I closed my eyes and wrapped my legs around his body to pull him deeper into me. With a slow pace we started to make love, his penis sliding in and out of my cunt. I started moaning. He sat up and grabbed my legs and spread them wide open. He was sitting just in front of my pussy and his cock started pounding into me again as his hands were holding my ankles spread as wide as possible.
As Harald was pounding into me hard and fast, I cold feel an orgasm cumming quickly. I started moaning louder and this was a sign for him to keep the pace steady and hard so that I would cum soon. With long and deep hard poundings he made me cum. My pussy made contractions around his shaft and I screamed it out. It was a fantastic orgasm that caused my legs to feel numb.
Harald stopped moving so that I could enjoy the orgasm as much as possible. His cock was buried deep into me. I love it when a guy has his cock all the way inside my vagina. He laid back on top of me and pushed his shaft as deep as he could into me and left it there. This made me crazy and I started contracting my pussy to squeeze his shaft.
“How about we go sit on the chair? Its been a while since we did that position.” Harald asked me breathing heavily. This was a position he loved. He removed his cock from my cunt and sat down on the chair in my bedroom. I crawled out off bed and walked towards him. I placed one leg on each side and sat down on his lap, facing him. I took his shaft and slipped it into my pussy. On the first move, I plunged downward driving it deeply inside me. My legs were draped over his shoulder and I started moving up and down, riding his cock. Harald laid his hands on my sides and helped me steady me.
My pussy was sliding up and down on his shaft and we were both moaning loud. I decided to quicken up the pace and was moving as fast as I could up and down on his shaft. Harald was squeezing my tushie as I was rocking his world. I lowered myself so that his shaft was back deep inside me. Slowly I started rocking back and forth, grinding on his lap, feeling his penis buried into me as he had his head tilted backwards. Suddenly he moved forward so that I had to wrap my legs around his body. He stood up and was supporting my body with his hands under my ass as he started tossing me up and down so that we were fucking standing up, my pussy gliding up and down on his shaft. This was a tough position so he couldn’t last for long and after a few strokes he sat back down on the chair.
“Oooh baby turn around will you?” he moaned.
I got up as his penis slipped out of me and I turned around. My hands were placed on his knees as I lowered my ass towards his penis. Harald grabbed my hips and guided me on his shaft and made it go back into my soaking wet cunt. My body started moving back up and down on his rock hard penis. He spanked my ass a few times. My legs started to get limp because I was getting exhausted by all this movement I had been doing. He noticed that I couldn’t keep the pace as fast as he would enjoy it so we stood up, his cock still inside me.
Harald moved the chair aside and spread his legs. He laid his hands around my body as I was standing up. His cock started moving in and out of me again. It felt so good. As the sex became more furious he was quickening the pace. I couldn’t keep my body standing up anymore so I had to bend over to find support with my hands on the bed. As I was leaning on the bed he fucked me harder. His cock was pounding in and out of my cunt, his balls slapping against my clitoris. The sound of a soaking cunt being fucked was filling the room.
He grabbed me by my shoulders and pulled himself deep into me. I was going to cum again soon. Harald grabbed my arms and pulled them backwards and kept them in some kind of lock so that I couldn’t move. He pounded hard and deep and all I could do was moan and be fucked. My knees started to shake and my legs getting numb, I couldn’t stand it any longer and was going to collapse soon. Harald noticed that and told me to lay down on the bed with my face down. We fell forward and collapsed on the bed. His cock was still inside me and he started pounding away.
I was cumming again, juices running out of my cunt, covering his cock. Harald was also exhausted and fell on my body to recover. My breathing was so heavy that I though I was going to faint. But Harald still hadn’t cum yet so some more fucking was awaiting me. He wanted me to recover so he grabbed his shaft and was slowly teasing me by sliding his cock over my pussy lips to my clitoris and back. He teased me some more by sliding is cockhead over my asshole. Neither of us had ever done anal sex before.
The juices that were covering his cock were now being smeared all over my asscrack. From time to time he moved his cock back into my cunt with a deep pound to pull it back out again so his shaft was covered with pussy juice again. He kept smearing it all up and down my asscrack. At one moment his cockhead was position against my anus and he slowly applied some pressure. I wasn’t expecting anal sex so I though he was just playing. To my surprise I felt my anus opening and his cockhead slipped in a very little. I guess he didn’t realize that because he pulled back and slipped it back into my pussy.
His cock was juicy again and he positioned it against my asshole again. He applied some pressure again and with ease his cock slipped into my asshole very slowly. A few seconds later I realized that his cock was inside my asshole a few inches! Before that moment I always thought that anal sex was going together with pain and discomfort. I tried to relax and slowly Harald started moving back and forth and moaning very loud.
“If it hurts baby, let me know and I will stop,“ he whispered in my ear. All I could do was nod because this was a feeling I never had before. Slowly his cock slipped deeper into my ass. At one moment it started to hurt and he noticed it by the look on my face. The pain was caused because the lower half of his cock was dry. It was not his thickness, not at all cause my ass easily accepted his cock. He pulled it back out and rubbed his spit over his shaft to make it nice and slick.
He slowly guided it back into my asshole. At first I was scared that it was going to hurt but it didn’t and he slipped it inside me all the way. I couldn’t believe that he was fucking my ass. Before I was so scared about anal sex and now it was just happening. I moved my hand under my body and searched for my cunt. I found my clitoris and slowly started rubbing it around while Harald was fucking my asshole. First he was moving slowly, trying not to hurt me. But when he realized that I was enjoying it too, he started to fuck my ass if it was my pussy, hard and deep.
“I am going to cum in your ass sweetie.” he cried out while he was pounding away.
“Please not in my ass sweetie.“ I moaned back.
He asked why not.
“Because I will get diarrhea.” I giggled.
The next thing I knew we were laughing out loud. I don’t know why but I just felt like saying that. Harald was so close to his orgasm that he started fucking again while I was still laughing. He was holding me by my shoulder as he was fucking my asshole hard and deep. His breathing was so heavy and his moaning so loud that I knew his orgasm wasn’t far away.
“Cum on my back baby.” I moaned.
Right before he was going to squirt, he pulled his shaft out and squirted all of his cum over my back. Jets and streams of cum landed all over my back while my anus was adjusting back to the feeling of not having a cock inside it anymore. After the last drops of cum were squeezed out off his shaft, he collapsed next to me. It was such a strange feeling to have just been fucked in my asshole - I couldn’t even describe it. After we had recovered we took a nice steamy shower together to relax.
After the shower we went back to bed and hugged and cuddled for a while and maybe more important, we talked about sex for a while and especially about the special and new experience we’d just had together. From that day on, we had anal sex once in a while. And every time I had my period, I had no excuse anymore to not have sex cause my asshole was always ready for a nice fucking.
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