Fantasy Night Ch. 02

I want to tell you about another great night with my boyfriend Tommy. If you read my first story, you know a little bit about us and our desires to keep our loving relationship alive and fresh by always communicating honestly about our emotional and physical needs. As a result, not only is our love for each other growing day by day, but the sex just keeps getting better and better!

Last time I wrote about my little bucket list of sexual fantasies and about one night in particular. On that night, at my request, I watched my lover masturbate right in front of me while I fingered myself to orgasm. This time, I wanted to explore a fantasy of mine that is well...anally oriented.

A little background first.

Tommy and I have experimented with anal play in the past. One night, while we were in a sixty-nine position, I was feeling a little bold. I had been sucking Tommy's cock and licking his balls when I decided to take things a little further, and I positioned myself so that I had access to his ass. I began licking closer and closer to his little butt hole, and then boldly swiped my tongue across his anus. Tommy kind of squirmed and shifted out of position and I took his action to mean that he was uncomfortable with what I was doing, so I backed off. We remained in the sixty-nine position and continued making love, me sucking on Tommy's gorgeous cock while he licked my pussy to orgasm.

A week or two later, we were again sixty-nining when my man starting licking towards my butt hole. I'm guessing that our previous session had got Tommy thinking about oral/anal stimulation and that he was interested in trying it again. When his tongue reached my anus, the sensation was wonderful, a mixture of physical pleasure and excitement. We were moving on to a new sexual adventure, one that was both erotic and taboo. His tongue felt really good and I moaned quietly, encouraging Tommy to continue.

After he had been at it for a few minutes, I shifted slightly, moved my head into position, paused for a second, then gave his ass hole a firm lick with my tongue. Tommy flinched, but did not move away. If anything, he positioned himself to allow me better access to his hole. I licked him there a few more times, and we began a sort of anal sixty-nine. We couldn't actually tongue each other's butts at the same time, so we periodically shifted positions so that one of us would have easy access to the others orifice.

We were both getting excited to the point of no return, when Tommy climbed on top of me, and while kissing me passionately, inserted his penis in my wet pussy. We fucked while kissing deeply and exchanging tastes. Our orgasms came quickly and we collapsed in each other's arms, falling asleep shortly thereafter.

So, this brings us to my fantasy.

My desire was to really focus on my lover's ass, to take my time and pleasure him anally with my tongue and fingers. And since it turned me on so much the last time we had fantasy night (you should read that story sometime), I might also ask Tommy to play with himself again tonight!

I prepped myself throughout the day for our encounter. I showered, shaved and applied a fresh coat of bright red polish to my toe nails. If you read my first story, you know that Tommy loves my feet and toes.

After a nice dinner and a couple of glasses of merlot, I ask Tommy to go take a shower then meet me in the living room. While he's showering, I poke my head into the bathroom and ask him to make sure and soap up his butt really well, knowing that this will get him thinking about what I might have in store for him.

When he's finished showering, he comes into the living room wearing a pair of black boxer shorts, one of my favorite looks for him. I'm sitting in one of our tall back chairs, wearing a long white satin robe. My legs are crossed, displaying my sexy calves and pretty feet and toes. I am also wearing one of Tommy's favorite pair of shoes. They're gold, with a four-inch stiletto heel, and just a couple of thin straps to hold them in place.

I've sat a glass of wine on the table next to me so that I can take a sip from time to time and I'm feeling quite regal, like a queen in her throne, with one of her subjects standing before her. Tommy obviously likes what he sees, which is made evident by the large bulge in his shorts. I motion for him to stand right in front of me. I put my hands on his hips, and plant a big kiss on the bulge in his boxers. A couple more kisses, then I slowly pull down his shorts to reveal his engorged penis. I waste no time, and begin kissing and licking my man's beautiful dick. I suck on the head, making it shiny with my saliva, as Tommy moans in pleasure. I lick up and down while gently fondling his balls. I spread open the pee hole with my fingers and lick and probe the slit with my tongue. Each move makes Tommy gasp and moan excitedly. But this fantasy night is about his butt, so it is time to move on.

I take a couple of sips of my wine, place my hands on Tommy's hips, and direct him to turn around, facing away from me. He does as directed, and now I have a great view of his cute little behind. Sitting in the chair will not give me the access I need, so I ask Tommy to take a couple of steps away from me, and I slip forward and kneel down on the carpeted floor. Now my man's butt is directly in front of my face, and thinking about what I'm about to do next has me both physically and mentally excited. My pussy is becoming wetter by the minute, and I can't help but finger myself and rub my clit for a short while before moving on to the main course for the evening.

I'm just about to reach up and grab his ass cheeks when I get a better idea. "Tommy", I want you to reach back and spread your ass for me". "OK, if that's what you want" is his reply. With that, he reaches behind and pulls his cheeks slightly apart. "Don't be shy honey, spread yourself wide open for me"

He does as I ask.

Now, right in front of my eyes, is my lover's ass, cheeks spread wide, with a clear view of his sexy little puckered butt hole. This whole scene is so turning me on. The idea that I'm about to lick his anus stirs many emotions. It's taboo, dirty...yet in another way, it's tender and loving; I'm placing my tongue on my lover's most intimate spot, showing him how much I adore him and want to pleasure him.

So here I go.

I move in close, and gently brush my tongue across Tommy's anus, just once to start. Tommy gasps. I tongue him again a few times, each time eliciting sounds of pleasure from my lover. He tastes clean and fresh, and has a slight scent of the lavender soap he used in the shower. I try experimenting with different techniques, alternating between light flicks of my tongue, broad firm swipes and light jabs. Tommy is loving every minute of this and is actually spreading himself wider, allowing me even better access to his hole. This emboldens me, and I make a point with my tongue, and slowly begin to enter him, penetrating the rubbery ring of his anus. Tommy moans loudly, encouraging me to go deeper.

At some point, my right hand had slipped between my legs, and I've been playing with my wet pussy and massaging my swollen clit. Now, with my other hand, I reach around and begin fondling Tommy's penis. He's moaning and beginning to shake and I'm afraid this will end too soon, so I release his cock and move on.

I want to play with his prostate next. I have another sip of my wine and grab a bottle of lube that I had set on the table. I'm about to squirt some on to my fingers when an idea hits me. "Tommy, I want you to lube up your ass for me." I take his right hand and apply a generous amount of the lube to his first two fingers. I so love my man! He's willing to try just about anything to enhance our lovemaking. While still holding his cheeks apart with on hand, he slowly smears some of the lube on his anus, and then tentatively inserts a finger inside. "That's it baby" I encourage, "stick it in deeper". He does. "Now move it in and out." And he does.

What a sight! I'm kneeling behind my man, my face just inches from his ass, and he's finger fucking his own butt hole, moving his finger in and out slowly. After a short while, I decide that I want some of this action, so I take his hand, and pull it slowly away from his ass. I lube up my own fingers and gently insert one into his hole. It feels warm and tight inside, and I begin to move in and out slowly. Tommy is loving the sensation, and I am loving the idea that I am probing so deeply into my lovers most intimate region and causing him such great pleasure.

While this is going on, I'm still playing with my pussy, so I don't have a free hand for Tommy's cock. I ask him to grab his penis and masturbate for me. He doesn't hesitate, and begins to pump his engorged cock while I finger his anus and massage his prostate.

At this rate, Tommy won't last much longer and I decide that I don't want to let his cum go to waste. I remove my finger from his rectum and turn him around to face me. He's still pumping away on his shaft and just as he's about to ejaculate, I wrap my lips around his cock and begin to suck. Tommy moans loudly and I feel his cum splashing against the back of my throat. I try my best to swallow every last drop as he shakes and moans with pleasure. When I'm sure that he's done, I release his penis from my mouth, stand up, and give him a big kiss.

I can tell that after all this stimulation, Tommy is weak at the knees, so I take him by the hand, and we move to the bedroom. We lie in each other's arms and rest quietly before finally going to sleep for the night.

One more fantasy checked off my bucket list!

-Jessica B.