Fantasy Night Ch. 03

If you have read my previous stories, you know that my boyfriend Tommy and I have an adventurous and loving sex life. I'm always thinking of new ways to keep things fresh and exciting for both of us. Sometimes it's about pleasing my man, and sometimes it's about fulfilling my own fantasies. This story is about role reversal, and although it's mostly about a desire of mine, I'm hoping that Tommy will love the experience as well.

Over the years, Tommy and I have experimented with various forms of anal play. I really love it when he makes love to me anally. The act excites me on many levels. There's the taboo associated with anal sex, that it's something dirty and forbidden. And the intimacy and trust involved, exposing oneself so completely to your lover, knowing that he will be gentle and caring. There's a little fear that it may be painful, and finally there's the actual physical pleasure of having a thick penis moving in and out or your anus. In my experience, once I relax and start to enjoy this incredible sensation, I just need to rub my clit for a short while before I experience an intense orgasm. And feeling my lover pump a load of his warm cum deep inside of me is the icing on the cake.

So as I said, this story is about role reversal. I want to know what it would be like to fuck my man in the ass, and I want him to experience the same physical and emotional pleasures that I experience when he does it to me.

I've played with Tommy's ass before. He loves it when I tongue and figure him back there, and on a couple of occasions, he has allowed me to insert a slim vibrator in his butt while I play with his penis. But this is going to be different. I really want to try and make this experience as much like the real thing as possible.

First, I did some research on the internet. I Googled "realistic strap-on" and found several models, and based on reviews and pictures, decided on a dildo called the RealCock 2. It was ridiculously expensive but it's as close to the real thing as it gets. I bought the strap-on compatible model which is made with three layers of silicone with a firm inner core and an outer layer that slides over the core like a real penis. The veins on the shaft are lightly shaded to give a very realistic color and the balls actually move around in the sack just like the real thing.

I didn't want to just spring this on my lover as a surprise, so I broached the subject during one of our foreplay sessions. "Tommy, I have a fantasy that I'd like to explore, and want to know if you'd be up for it." "I'd do just about anything for you babe." was his response. So I told him all about my desire to have anal sex with him, but with me doing the penetrating. Without hesitation, well maybe just a little, Tommy agreed that he would be willing to give it a try. We both had the upcoming Saturday off from work, so we decided it would be a good time for our experiment in role reversal.

All Saturday morning, I thought about what was going to happen that day. At breakfast I asked Tommy if he was still up for what we had talked about. He paused for a second, and answered, "I'm a little nervous, but yes." After a light lunch, we decided to go have a couple of drinks out by our pool just to loosen us (especially Tommy) up a bit.

Then it was time. I wanted us to shower separately so that I could make a grand entrance in the outfit that I had decided to wear. I showered first, and while my lover cleaned himself up, I got myself ready. I asked Tommy to wait for me in the living room. When I entered the room, he was sitting on the couch wearing just a pair of boxer shorts. His eyes opened wide and the look on his face was a mixture of apprehension, excitement, lust, and maybe a little bit of fear.

I stood before him wearing a tight-fitting black blouse, blue jeans, and black strappy stilettos which exposed my freshly painted black toenails. But what had my lover's attention was what was protruding from my unzipped fly. Tommy was staring at my very impressive cock and balls. The look on his face was just priceless!

I walked towards my lover and stood in front of him, my cock just inches away from his face. Tommy wasn't sure what to do next, so I made things easy for him. Without a word, I dropped to my knees, removed his shorts, and began working his penis. I tried to move slowly, but I was so excited that it wasn't easy. I tenderly licked the head of his cock, tongued his pee-hole and licked up and down the shaft before sucking as much of him into my mouth as possible. I kissed and licked his balls slowly but firmly, using broad strokes of my wet tongue. Then I stood up and told him it was time to switch places.

This is what I had been lustfully anticipating all morning. I sat on the couch and pointed to the floor. Tommy understood and knelt between my legs. His eyes looked up to meet mine, and I pointed down at my penis. "Kiss it" I said, and after just a moment hesitation, my lover planted a kiss on the head of my cock. The visual was so arousing that I swear I could almost feel it. "Lick the head Tommy" and he did. "Now stick it in your mouth and suck." No more hesitation, Tommy was doing as I asked and seemed to be enjoying it as much as I was. "Now lick the shaft baby" I instructed, and I watched as he ran his tongue up and down my cock as his hand instinctively began to fondle my balls. "You're doing great, baby, now lick my balls, kiss them, suck them into your mouth!" I could not believe the words that were coming out of my mouth, but I was just so turned on that all inhibition took a back seat to pure lust.

Tommy crouched down and began to lick my balls as he fondled his own sack. "Now grab your cock lover, and masturbate for me," I instructed. Tommy has done this for me before, and watching him pleasure himself right in front of me was a real turn on. Watching my man lick my artificial balls while running his hand up and down his own cock was more than I could stand.

I couldn't wait any longer. It was time for the main event. I motioned for Tommy to get up, and asked him to kneel on the couch with his arms resting on the backrest. This gave me perfect access to the object of my desire, my lover's sexy little butthole. I knelt on the floor and massaged his cheeks, spreading them apart to view my intended target. I wanted Tommy to experience all the pleasures that I have felt when the roles were reversed, so as he has often done to me before entering my ass, I began to relax him with my tongue. I gently kissed and licked around the opening and then softly licked his anus. My excitement mounting, I quickly became more aggressive, alternating between deep forceful jabs and broad strokes with my tongue. But it was time. I needed to fuck my lover.

I grabbed a bottle of lube and began to grease up Tommy's anus, applying it to the outer ring and using my finger to probe deep inside. I was about to lube up my cock, but decided that it would be more fun to let Tommy do it, so I positioned myself so that my penis was if front of my lover's face. "Suck it for me one more time, baby?" I asked, and he did as I asked, placing that ultra-realistic phallus of mine in his mouth, and sucking on it passionately. "That's wonderful baby, now grease me up for your ass." Tommy took the bottle, squirted some lube on my cock, and used his hand to apply a nice thick coat to the head and shaft. My new phallus looked even better now that it was glistening with lube. I could wait no longer.

I changed positions again, this time standing behind my lover. My four-inch stilettos placed me at a perfect height for penetrating his ass. This was it. I spread his cheeks and placed the fat head of my cock into position. Hoping to prolong the experience for both of us, I began to tease my lover by slowly running my cock between his cheeks, pausing briefly as I rubbed it across his butt-hole. The anticipation really getting to him. His breathing was getting heavier and he would flinch every time my cock touched his anus. And then I zeroed in on his hole. I began to exert slow but steady pressure and Tommy began to squirm a bit. "Okay lover?" I asked, and Tommy replied "yes, keep going, but go slow." I exerted more pressure. I started to get concerned that maybe it wouldn't go in, and then all at once, the shiny head of my cock popped into my man's asshole. At this, Tommy let out a loud grunt. "Still okay" I asked." It hurts a bit honey. Give me a minute to get used to it then keep going."

I waited a minute or so, and then tried to push in a little further. Tommy responded by actually pushing back to meet my slow but steady motion into his rectum. This was it! What an incredible sight. My cock was a third of the way in my man's gorgeous butt and I began to slowly pump in and out. I reached for the lube, pulled my cock almost all the way out, and smeared some more of the slippery liquid all over the veiny shaft. Then, in one slow but steady motion, I slid the entire length of my cock all the way up Tommy's ass. He let out a loud gasp, but did not protest. I began fucking my man in earnest. Not too fast, but with steady long thrusts. With each in and out motion, Tommy moaned deeply and I was in heaven! Watching my cock penetrate his inner depths turned me on in a way that is hard to describe. There were feelings of power and control, mixed with tenderness and love. Combined with the role reversal aspect that had so intrigued me at the start, well I was just loving this!

My man was moaning with every thrust and his breathing was growing faster. I decided it was time to make him cum. Once again grabbing for the lube, I squirted some on my hand and reached around to massage Tommy's cock. Just a few strokes, and I could tell that this was not going to take long. I started to pump away, and Tommy began to shake and moan as I continued to penetrate him deeply. In this position, I could no longer see what was going on, so I just had to imagine the sight of Tommy's sexy butt hole stretching to accommodate my thrusting cock, while I masturbated him towards orgasm.

Tommy's breathing increased and with one final load moan, he began to ejaculate into my hand. Stream after warm gooey stream hit my hand and dripped on to the couch. Inspired, I pulled my cock partially out of my spent lover's ass and smeared his cum all over the shaft before pushing it back into his hole. I moved slowly in and out a few more times, and fantasized that I had actually ejaculated in Tommy's ass, and that it was my own cum seeping out of his well fucked hole. One last slow thrust deep into my lover, then I slowly pulled out, watching every inch of my cock slide out of him. I went as slowly as possible, enjoying the incredible view one last time.

I then helped my lover up to his feet and directed him towards the shower so that he could wash off all the lube that I had applied to his cock and butt. While he cleaned up, I undressed, removed my strap-on gear, and changed into something comfortable to wear until bedtime.

When Tommy got out of the shower, I was waiting with a couple of glasses of wine. We sat and drank and talked until we were both ready to retire, then settled in for a good night's sleep. The evening was everything I could have hoped for. One more great sexual experience shared with the man I love.

-Jessica B.