This one became quite focused on the actual act, but well, that is what it was about for me.
In the summer of my last year at university, I still had to complete a mandatory internship. I went to another city for three months to work in the compliance department of an investment bank for the summer. It was summer, this story I’m about to tell took place before the Lehman bankruptcy, and I had no ambitions to get a contract at the bank. So, all in all, the work didn’t take up too much of my time and I had more than enough time to explore the city, which was foreign to me.
The sister of a friend from university lived there. Through her, I quickly got connected to others as well. Among them was Luisa. Like me, Luisa still went to university. Luisa took life easy. She had a natural optimistic attitude towards life, which she obviously enjoyed to the fullest. Her good humor was contagious. She made no secret of what she wanted and what she liked.
She obviously liked me. So it happened that we had a first date in fairly rapid succession, kissed for the first time and finally ended up in bed. Between the two of us it was unspokenly clear that we did not want a long-term relationship, but wanted to spend a relaxed summer together. That included a lot of sex – a **lot** of sex. After a few days, we spent most nights together either at her place or mine.
Luisa was rather small and slim. That gave me with my height of 1.80 meters and neatly trained 81 kg a completely different presence during sex than I had been used to from my previous partners. The most obvious advantage was that no matter in which position we did it, all parts of Luisa’s body were always within reach for me. Furthermore, it surprised me to find that Luisa always slept in just a T-shirt without panties. More than once, my fingers found their way under her shirt and between her legs where my cock soon landed, too, in the evening, in the morning or even at night when we were half asleep.
On one of those occasions in the middle of the night, when Luisa was riding me hard and I was clutching her little ass with both hands, my middle finger found its way to her anus. I was very cautious when I realized where I had landed there. But when I couldn’t notice any defensive reaction, I started a little more briskly with circular movements around her backdoor. This in turn seemed to please her. I began to exert some pressure. Whether it was just by the pressure I exerted on her anus or by the fact that Luisa, while she rode me, pressed herself once more against my finger, a member of my finger was suddenly stuck in her butthole. Luisa continued to ride me with undiminished ferocity until she came on top of me.
Luisa didn’t seem to think my playing on and in her butt was worth mentioning, so I didn’t mention it either, even though it was a completely new experience for me. Over the next few days and weeks, it became a regular part of our lovemaking that I put my finger in her butt hole when she rode me. She liked it, sometimes I even had the impression she demanded it. Without asking, I was pretty sure my finger wasn’t the first thing she had in her butt during sex. I struggled with myself to find the right time to ask her about anal sex, but I didn’t want to reveal my inexperience in it. So I stayed for the time being to explore her backdoor with my finger.
We had our routine. During the day we both went our separate ways, the nights we spent together. We had sex almost every evening, occasionally enriched by a quickie in the morning.
One evening, a while after me, she came out of the bathroom into the bedroom. I was already lying in bed. She came towards me in her usual pajamas. Her shirt was only so long that it just covered her pussy. She came towards me smiling with an accentuated swing of her hips, walking lightly on her tiptoes. Her playful nature made my already existing anticipation turn into pure horniness.
Luisa crawled to me under the covers and began to kiss me greedily.My hands grabbed her demanding. My right hand sank down to her bare thighs. I ran my hand to the curve of her buttocks under her shirt. My hand froze as I grazed something hard. My hand stayed in place. I released my lips from hers and looked at her in surprise. Her smile turned into a challenging grin.
“What’s that?” I looked at her in disbelief and fascination at the same time. She breathed into my ear: “I thought you might like to stick your dick up my ass for a change. Would you like that? It would make me so hot right now…”. In the next moment she turned around lasciviously, as if she would go into the spoon position. At the same time, she pushed down the covers until her butt was revealed. Lying sideways, she stuck her butt out. I moved away from her a bit and slid lower to get a better look at her butt.
Between her buttocks protruded the flat end of a black butt plug. I pressed lightly on him. Luisa acknowledged this with a pleasant moan. I bit lightly into one of her buttocks. My cock was now hard to the max.
Luisa rolled on top of me and reached for my cock inside my boxers. “Strip.” I peeled out of the shorts while Luisa, lasciviously stripped off her T-shirt. She was now kneeling beside me. She demonstratively licked herself wetly over one palm. She reached for my cock and spread her spit over my hardness. After a few moments of playing with my cock, she reached over to the nightstand and pulled out a tube of lube. She put a thick cap of the gel on my cock and then spread it liberally on him. At some point it was so slippery that it smacked as Luisa jerked along.
Obviously satisfied with her work, she turned to me and gave me an intense French kiss without letting go of my cock. “Come behind me and fuck me in the ass.” I stood up and stepped to the edge of the bed behind her. Luisa slowly and lasciviously turned her back to me until she was kneeling on all fours directly in front of me. Over her shoulder she looked at me and reached for the butt plug that was still stuck in her ass. She pulled it out with a slow steady motion. “Now you.”
I stared at her well-oiled, stretched anus. I firmly grasped her pelvis with both hands, bent forward slightly, and stood slightly on my front feet, bringing my cock into position at her butt hole. “Now go real slow, cowboy.” she gave me on the way, when my glans touched her anus for the first time.
Trying to keep my balance, I slowly pushed my pelvis forward. I felt tension in my cock when her anus did not immediately yield to my pressure. I shifted my weight slightly forward. At that moment, my hard cock slid a tiny bit inside her. I was probably breathing in deeper than she was at that moment. I felt the firm pressure of her anus around my cock just below the glans.
Carefully I shifted my weight to have a secure footing, then I let my pelvis perform very small pulsating movements. After a few movements I dared to penetrate deeper. Luisa acknowledged my advances with clear acoustic utterances. After a while I was able to fuck her relatively deep in her little ass with loose movements of my pelvis.
I enjoyed my anal deflowering to the fullest. It helped a lot that Luisa obviously was pretty experienced and well prepared. The tightness of her backdoor, in combination with the horny sight of her ass and her acoustic background drove my horniness to the immeasurable. At the same time, I was careful not to hurt her or otherwise overdo it. For my part, I began to audibly express my pleasure. I was unsure how far I was allowed to go. At some point I pressed out, “This won’t last much longer.”
“Go on, get it” she returned between two heavy breaths. She didn’t have to tell me twice at that point. I held her tight, allowing myself two or three more thrusts before I discharged heavily. My orgasm shook me. I slowly pulled out and slumped on the bed next to Luisa. She remained in an almost unchanged position. Leaning over briefly, she kissed me. “I’m glad you liked it. Give me two three minutes head start and then get in the shower. I expect you to return the favor…”
Source: reddit.com/r/gonewildstories/comments/rve0dq/mf_my_introduction_to_greek_love