A New Horizon

This is a short but real story about a first time, which happened to me in the early 2000s, a time before smart phones were around, most people over 30 had no clue how the internet works and Tarantino´s Kill Bill 1 would be entering the movie theatres soon.

My girlfriend Heather and I were in our early 20s. It was a rainy afternoon, so we decided to stay at home and enjoy some quality naked time at home together. We were quite comfortable with our bodies and made a point out of coming up with new things to explore together frequently. This way we have tried out many different positions, bought our first sex toys (ok, they were mostly hers) and have enjoyed some light bondage with a little bit of blindfolding together, to keep things spicy.

When we rushed out of our clothes, neither one of us had a clue, what was going to happen next and we loved the freedom this offered to us. I laid on top her which maximized the amount of skin contact with each other and it felt warm, close and it felt like.... more!

We started making out and rolling around, alternating who was on top and who was at the bottom. She knew that her big breast always felt amazing to me and she was not shy to run them up and down my body. Soon I couldn´t hold myself back anymore, so I pinned her down on her back, looked her deep into the eyes and slowly kissed my way down her body. I started kissing her breasts, burrowing my face in between them and gently sucking on her nipples. I went further down, where I ran my goatee around her bellybutton and kissed her all over her belly. I kept lowering my head further and further and because she was freshly shaven, my kisses could reach every spot of her soft skin. She started moaning and when I spread her lips with my (other) lips and I could taste how her lust increased from one moment to the next when I slid a finger inside. Her orgasm soon followed after I decided to use a second finger and move them in a little "come over here" gesture, while the tip of my tongue consistently circled around her clitoris.

After this we decided to include a little vibrator-play for her, so in order to avoid soreness we pulled out some lube from the drawer next to our bed. We then went on with what had become a well-choreographed routine that made her climax again within a few minutes, not so much due to my efforts, but rather through the technological superpower of our little helper. While this left her with a post climactic hypersensitivity, preventing us from entering round two straightaway, it had also made her very horny and hungry for more action.

This is when she started focussing on me, running her hands up and down my body, kissing me passionately, teasing me with her tongue and eventually she grabbed my cock, which was hard in anticipation of what was to come next. After a little while, she went down on me and she too knew exactly which buttons to press to drive me crazy. But this time when I started to moan, she stopped abruptly and looked me straight in the eyes as she grabbed her toy and asked me if I would mind her trying it on me.

In my sex-crazed mind, I stared at the pink vibrator, which was shaped like 'the real thing' and had the length and girth of a good average-sized male equipment. This was new territory and I certainly had not entertained the idea before this moment. Anal play had never intrigued me and being penetrated sounded rather painful, which is something that did not fit in with my idea of erotic pleasure.

Nevertheless, I was hard, horny as hell and I still had her 'perfume' all over my face, which did not help in making a rational decision. Part of me still realized, that I was in over my head and the word consent could not be used in the strict sense here; but I agreed and nervously asked her to get some lube. I was still laying on my back, when she spread my legs, carefully took my semi-erection to rest it on my stomach and gained access to my virgin butt.

There she was, a short redheaded and stunningly beautiful woman towering over me. The fact that she was literally 30 cm shorter than me, became entirely irrelevant in this position and the excitement in her eyes, her mischievous smirk and ample breasts finally convinced me, that she was the right person to do this with.

She winked at me and quickly prepared her tool with a squirt of KY-jelly. My legs were spread wide, my knees pointed to the ceiling and my feet were comfortably positioned next to my butt cheeks when she started to slide the toy along my crack. It was a strange and new sensation, which felt a little bit like a massage until the tip began to first rest on and then apply pressure to my hole. I tensed up a little, but a few reassuring strokes of my cock with her free hand almost immediately put me at ease again.

Slowly she increased the pressure on me, so bit by bit, my sphincter relaxed and widened. It was uncomfortable at first, but after a while, her lips and tongue joined her hands on my front, which made the experience very pleasurable. Due to the immense pressure I could feel, I had assumed that the tip of the toy had been inside of me for a little time now. But then it happened: I fully relaxed my muscles and half of the dildo slid inside of me at once. The sensation of my violently stretched hole hurt a lot but was immediately accompanied by the pleasure from my prostate, when the well lubed shaft slid by it. My eyes popped wide open and my brain could not make sense of the intense but quite opposite signals it was perceiving.

I gasped and asked her to stop, so she halted all movements and asked me if I was ok. When I could not produce an answer right away, she decided to take charge and distract me from the pain by taking my now soft penis in her mouth and gently sliding her lips up and down, reviving its spirits straight away. Her plan worked and after a few moments, the pain was gone. Now I could start to explore the feeling of having a foreign object inside of me. It had an unignorable presence, which I had never felt before and not even a sloppy blowjob could fully distract me from it. All I could think was: "Oh my god, it´s really inside of me!"

Apparently, my reaction had quite an effect on Heather as well. She seemed to drink in my facial expressions and carefully watched every movement of my body to make sure I enjoyed myself. I could see that she was really turned on by this new game, while I was still overwhelmed with a lot of conflicting sensations and emotions. It reassured me though, that she clearly did not try to dominate me, but rather to explore a new source of pleasure with me. I was sweating without even moving my body.

Carefully she started moving the toy inside of me and soon she was going back and forth. I realized I was being fucked gently with a realistic silicone cock and a brief onset of shame was soon washed away by pure lust. I was amazed by the feeling of my manhood being stimulated at its root rather than the tip and every time the shaft slipped by my prostate, it excited me more than the previous stroke. After a while, she started to push it deeper into me and I found out that in addition to the girth, there is a length limit as well, that requires some getting used to. It again hurt a bit, but once she had found a good rhythm, I got accustomed to its full size inside me and soon I could fully enjoy her toy.

She went faster and faster and it was visibly difficult for her to co-ordinate the motions of her left and right hand, but boy, she managed to do so exquisitely! After that, it didn´t take very long for me to erupt in the biggest and longest orgasm, I had hitherto experienced. I blew a huge load all over my belly and Heather almost seemed to enjoy the warm mess as much as I did. I think she was proud of having the power to give me such an enormous level of pleasure.

It was right away clear to both of us that this was something we wanted to explore more. There was a whole world of sexual pleasure that we had never experienced, or even considered because of the taboo attached to it. Needless to say we made butt play a regular thing for the years to follow...

The End?