Anal sex with Max

Emily made sure that her boyfriend’s cock was not only erect, but also properly lubricated. Dani took out the plug from my ass and added some more lube to my hole. I simply laid on my back on the bed and eagerly awaited to finally be fucked by a real cock. My own penis was semi-erect from the sheer excitement. Finally we were both ready and Max approached me with a lustful smile on his face. Dani hopped onto the bed and sat beside me. She began to caress my smooth skin, she looked nearly as excited as I did. Emily remained next to her boyfriend, ready to assist. Max gently grabbed my nylon-covered ankles and spread my ong legs wide. My sister squatted down by his side and pushed his penis at my waiting anus. Max carefully pushed his loins forward.

“Mhmm,” I moaned audibly when the fat head stretched my sphincter. I was fully in my role now, so my moan was as feminine as my appearance.

Max did not stop, but continued to push his cock deeper into my ass. He was not larger than the biggest of the dildos which I had used to practise, but it felt different; flesh was so much better than plastic. We had merely begun, but I was already enjoying the experience. Dani continued to softly caress my skin; our eyes met from time to time and we exchanged smiles. Max was being gentle, but once his whole large penis managed to fit into my ass with ease, he realised that I was not so fragile. Still holding my ankles, he put them on his shoulders. With an odd type of vanity I admired how shapely and feminine my stockings-covered legs looked in this position; white hosiery really suited me. Max grabbed my thighs and pulled out his cock, not completely though, its head remained inside of my ass. He shoved it back in almost immediately, this time his motion was quicker and more decisive. My moan was louder and apparently encouraged Max to skip the preparations phase already. He checked his grip on my thighs and began to fuck my ass.

Dani reached between my legs, all she had to do was to caress my semi-erect penis for a moment for it to become fully hard. Her touch was soft, she clearly wanted to keep me as aroused as possible, but not climax just yet. Max had decent stamina and obviously my girlfriend did not want to spoil the fun for me by making me cum prematurely.

Max’s pace was slow at the beginning, he was still ‘testing the ground’; which was fine, because I needed to adjust to him as well. His shoves were deep and thorough though, each time he would withdraw almost his entire cock, leaving only its head inside of my anus. I groaned quietly whenever he shoved his whole penis. Remaining in my female role became natural for me, so my voice was as feminine as I could make it. Eventually Max began to speed up his motions, his shoves remained just as deep though; the volume of my moans increased as well. Dani continued to keep my cock hard and close to the edge, but made sure to never go too far. She knew my body well enough to be able to achieve that with ease.

Max’s loins were hitting my buttocks with considerable ****; it finally became a proper fucking. He was holding my thighs firmly for support and I could see in his lustful gaze that he loved pounding my ass; his enthusiasm and desire made me feel even more feminine. Once he found his preferred pace there were no more deviations. Max fucked me hard for several minutes before he announces his climax with an audible grunt. Dani quickly noticed what was happening and needed a mere moment to make me cum as well. While Mike shot a voluminous load inside of my ass I shot a load of my own onto my belly. He continued to pound me in short, forceful, but somewhat hectic, motions, until the final drop of semen left his balls. Max kept his penis inside of my ass, while he caressed my long nylon-covered legs. Fortunately he did not have the urge to kiss me; this was Dani’s job and we shared a long sensual kiss. When Max eventually withdrew his cock from my anus Emily swiftly approached me with a butt-plug in her hand.

“You’ll clean yourself in the bathroom,” she said with a smirk, “no need to make the sheets even dirtier.”

“You sure know how to maintain the mood,” I replied and showed her my tongue.

In the meantime Dani put her own tongue to work; she began to lick my semen from my smooth belly. She swallowed most of it, but snowballed a few drops into my mouth when she later kissed me.

Before taking a shower Dani and I made love, alone this time. I kept the lingerie on and the anal-plug in. It was marvellous.

It was difficult to call this experience my ‘anal deflowering’, because after so much pegging I was far from being an anal virgin; but it was my first time with a man. Even though I had sucked cocks already and even swallowed cum, but this felt different. Most importantly I had enjoyed and I wanted more; so did Max, but for him it was Emily who set the limits. Fortunately I had other boyfriends who would certainly be eager to take my ass. Together with Dani we decided that Ricky would be next.