Just when he thought it would never happen – it happened. There’s a first for everything. This would be HIS first time experiencing anal sex as a bottom. Jacob and I had been dating on and off all during high school. We had a lot of kinky sexual experiences during those years but never explored him taking it in the ass. Sure we joked around about how much he wanted me to be the first to fuck his ass, but we never pursued his Anal Cherry Popping…Until.
It was the summer of our Senior year – we had just graduated and we were off to separate colleges in the fall. We had been drinking all day and after a few more shots he finally gave into his inhibitions and popped the question. (Wicked LiL Laugh) No, he didn’t ask me to marry him!! I could tell that his anticipation had been building for hours. He couldn’t hold back any more!! He asked me to pop his cherry. How funny is a man asking to have his Anal Cherry Popped?
His anticipation grew stronger with each passing moment. I wanted him to relax and ride the ride. Everything would go smoothly from start to finish. Jacob was a husky guy that stood 6’2 and 195 pounds ALL muscle. I was going to break him in like a first-time virgin slow and steady. Well over the next couple of hours, we prepared for the anal christening by putting a butt plug in and watching a few domination strap-on porn. I had to laugh a few times cause he kept flip-flopping back and forth “Yes I want to do it,” he said then he would change his mind. I kept reassuring him that the pleasure was worth the little pain. This would be an experience he would never forget.
Needless to say, he kept thinking about it over and over again. He would watch the porn and get so turned on that he couldn’t help to jerk off his throbbing 10-inch cock. I commanded him to stop touching himself. Consequently, I didn’t want him to blow his load before I got to fuck him with my strapon. We needed to get his anal cherry popped sooner than later. Everyone knows – once a guy blows his load, it’s all over. There would be no popping his anal cherry. I had to keep the ball rolling before he would chicken out.
It didn’t take much coaxing once I started using my magic tongue and fingers. I had Jacob at my mercy as he submitted to me and pulled his legs back to reveal his ass. Once I pulled his butt plug out, he was fully exposed to me. At this point, I knew I could have my way with him. I grazed over his cock with my tongue and made my way to his hungry ass. Slowly licking and teasing him, I diverted his attention with the pleasure of a little tease and denial. I couldn’t resist giving him a Rusty Trombone, as I stroked his cock. I swirled my tongue around his hungry asshole and soon he was begging for me to fuck him. (Wicked LiL Laugh) He didn’t need to ask twice.
Within minutes I had my beautiful strapon lubed up and ready to take his anal virginity. He closed his eyes as I slowly slipped inside him inch by inch. He released a gasp of ecstasy as I worked myself in and out in perfect rhythm. His cock grew even hard with each thrust into his hungry pussy. He couldn’t resist the gratification he was feeling as I massaged his prostate with my strap-on. In and out – deeper thrust he was completely mine as he blew his load. That may have been the first time but it sure wasn’t the last. We had the rest of the summer open to explore kinky anal play and more.
Let’s explore your fetish and fantasy needs, as we play together. I want to tease you in addition to pushing your boundaries. Ready to have some of the BEST Kinky Fetish Phone Sex? To sum it up…I have something just for you. Want free phone sex minutes ADDED to your paid call? FIRST-TIME CALLERS ONLY – Mention Anal Cherry Popping 5, when we connect. Anything goes No Taboos Phone Sex I’m waiting to begin our unique sexual adventure.
Furthermore, let me teach you the Pleasures of Phone Sex with No Limits. Enjoy my Blog – Divulge Your Dirty XXX Secret and the Rest Will Follow All good things always follow when you let me introduce you to the Taboo World of Fetish and Fantasy – Hence incorporating ALL your wicked little needs into our call. (Wicked LiL Grin) Can you do it for me? Maybe you should let me guide you in a direction you never imagined! Subsequently, step outside your vanilla world and slip deep into My World of Pleasure.
Furthermore, my sultry voice will capture you and keep you coming back for more. No worries all in all I will make it as pleasurable as possible. Additionally, Remember it’s ALL about pushing outside your comfort zone and not holding back! Certainly, we can explore ALL your fetish together. Furthermore, the opportunities are endless. Above all let me trigger your inner kinky side as we explore Anal Cherry Popping. Always remember – Above All – Our Only Limitation is Our Imagination. Call me and Let’s cum together. I’m waiting for you now so we can begin another hot journey.
I’m waiting for you…..and ONLY you!!!
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Jamie will do whatever you tell her. So don’t be shy use all her fuck holes.
Megan does family roleplay so well. The perfect deviant mom to her son.
This girl is a true goddess. She remembers my darkest fantasy from call to call. She role plays as someone whom I’ve always wanted to have sex with but will not act on, I’ve told her so much about this that she acts just like this person during the call and always makes me explode in my pants. Kali is the best!
Oh Wow that is ONE AWESOME GIRL! I ENJOYED Her it was my first time and Now I am wanting to do it again 🤣
Raven is Awesome and Perverted as usual. Love her to death!
Dawn got into the family role and ran with it. She was Perfect!
Megan took my idea and ran with it. Her mind is as perverted as mine. A must call.
Chloe is a very caring person. We tuned in together in a instant and made for a relaxed time. She deserves 5+ stars!!
Vivian is one sexy and nasty milf! Such a sexy voice and so experienced! I honestly felt I was with her during our call! …so amazing!!
It was one of the best experiences that I have ever had. I will definitely be back for more with Vivian..
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