He took her anal virginity and she loved it

After I found the memories I was looking for, I could watch, more like experience them. It was not like they lay before me in an ordered fashion and there was nothing chronological about it. They were hard to make sense of given what little I knew about her life before I moved into the flat next door to hers. But one memory in particular managed to catch my eye: This guy, she first met him in school but their relationship did nlt start until after he had left the school and she was about to do her final exams. That was about two years after he left. He was handsome to her, tall with brown hair, soft eyes with a nice smile and most importantly he was treating her like a grown up. He appeared gentleman like in most occasions to her but always in a youthful, easy way. Seemingly he was more experienced sexually then she was, but at that time she wasn't inexperienced at all herself it seemed.

In that memory, they were both a bit lit, at his place. I watched from her perspective as he kissed his way down her neck along a simple yet elegant black bra, his warm fingers removing the shoulder straps revealing her white breasts. The soft fabric of her bra sliding over her erect and sensitive nipples, slowly exposing them to the cold air first, quickly followed by his hot breath, soft lips and gentle kisses. I almost felt his hands on her body moving down across her flat stomach, playing with her belly button before sliding towards her panties. Matching her bra they were black, simple yet elegant, clinging nicely to her round ass, not too revealing or uncomfortable but definitely hot. She had chosen that pair of underwear specifically for that evening. His lips escorted her panties all the way to her ankles and he looked her straight into her eyes as he carefully removed the piece of fabric and then kissed his way back to her pussy. That day she had the hair on her pussy cut short and neatly trimmed. Not cleanly shaven, but with a soft and thin haircoat that even covered her outer labia. When his kisses reached her labia his tongue carefully entered her folds and caressed her clit. He sealed her pussy tightly with his mouth and slowly yet strongly pushed more of his tongue inside her, he moaned and the vibrations of his moaning sent shivers through her entire body. His hands moved under her ass and he lift her up a little as he licked her closer and closer to her first orgasm. I could feel her fingers softly tugging his short hair, pulling his head between her wide spread legs, her climax building up. And as she came she let her hands fall to the side, gripping the sheets tightly and bucking her hips against his mouth while every muscle in her body spasmed. His tongue was eagerly taking up her juices as he licked her through her strong orgasm, going slower as she finally came down from her orgasmic high. He pulled a pillow under her lower back, letting her rest her hips a little and getting his hands free to caress both her breasts. He immediately seized the opportunity and began to build up new arousal. I felt her panting, the waves of the first orgasm had just receded and the next was already building up. He let his right hand wander down from her breast, placed it with spread fingers, covering as much of her body as he possibly could, on her stomach while he put his thumb on her clit and began massaging her. When she was close, I could feel her second orgasm approaching like a tidal wave but he pulled away. I felt her confusion and saw her hands from her perspective reaching for his boxers, to free his cock. But he gently took her hands and looked her straight in the eye, „I want to do something special for you, Diane. Do you trust me?” I could feel her nodding slightly rattled. „I promise, I will be extra careful. It might hurt a bit at first. But I promise, you will love it. Just relax, okay?” „What are...” „Just go with it. I love you, Diane.” Again she nodded and he licked her some more before he emerged again and helped her, roll over. „Now lay on your stomach.” I could feel her lying down, her hips lifted by the pillow and his tongue licking her labia and working their way slowly towards her bottom. His warm, strong hands griped her cheeks and spread them gently, but as his tongue moved up, I could feel her tensing awkwardly. „Relax, Diane. I am absolutely comfortable with you, with your body. There is nothing to be ashamed of. Trust me.” And I could feel her relax. The feeling of his tongue encroaching her asshole was weird at first, but his other hand was still gently pleasuring her clitoris, keeping her lust up. „Don't be scared, this is a little wet”, he said as he pulled some lube between her butt cheeks. Although ist was obviously warmed, it seemed cold to her. His fingers began running the lube over her ass, between her cheeks and around her asshole. She squirmed out of surprise as his index finger entered her rear ever so slightly and she gasped a little. „Are you going to fuck my ass?” „Do you trust me Diane?” „Yes, but I am not hmmmmm” He applied some pressure on her clit while the index finger of his other hand gently caressed the inside of her butt. „not sure about my aaannghmm hmmm my ass.” He planted a few light kisses on her arching back. „Close your eyes, Diane and go with it, please. Relax, everything will be okay. I promise. You will love it.” „Ohmm okay but pleaaase. Be gentle.” „Shhh” He took time to massage her but hole and applied more pressure only very slowly to it and I could sense her coming to terms with the strange but more and more pleasurable sensation. After what seemed like an eternity, he pulled away his fingers and removed his boxers, probably applying lube to his cock. I could feel the tip of his cock touching her rear entrance and her of course tensing up, but his hands across her back and his soft low voice made her relax again. „You are ready, Diane. Trust me, you can do this”, and with this words, he applied increasing pressure, widening her butt hole bit by bit. She squirmed and gasped loudly before his glans had fully entered and he retracted again, only to come back and go a little bit further this time. „Ahhng. It's... hmmmm... iinnnntense.” „I know.” He took one hand of her hands and led it to her clit. „We're almost there, girl.” He retracted again and let her begin rubbing her clit, what she immediately did. Even with the tension and the anxiety, her arousal was still high and I could feel it being ready to take the lead. „Haaa! Huhhhnghmmmmm.” She panted. There was the intense sensation of something widening her butthole, entering her body, filling her up and her sphincter sealing her tight around the foreign object immediately after the broadest part had passed. The feeling of fullness, putting slight pressure on her pussy walls from the other side... She almost immediately began to adjust to his size and take pleasure from that weird new sensation. „Are you...” „Yes. You like it?” „It... Hannghm... It's weird. But...” She began to slightly move her butt pressing against his lubed member and letting a little bit more of his manhood enter her. „Hmmmm. I...” „Don't talk now” he said, as he slowly and and carefully began to fuck her. I could feel the orgasm, that started to build up what seemed like hours ago now approaching her fast and powerful like a **** of nature. In her memory she now was on all fours but I did not notice her getting up. He could not have been in her for long but in this part of the memory she groaned in pleasure gripping the sheets experiencing a long and powerful climax through his gentle thrusts... He moaned and gasped, speaking her name in an asking tone, „Diane? I ng I hmm” „Hmmyeas. itsn. Just cum!” And with a last gently thrust inside her, he began to pump his seed in her ass, a weird feeling that...

„D? You okay there?” „What? Uhh, yeah, I'm uh, I'm fine... I guess” „Dude you were gone like minutes! While I was trying to have a conversation with you, but you just stared at the wall! I started thinking about a bucket of ice water or something.”