The Next Day with Dennis

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Janice and Dennis try anal sex for the first time.
1.4k words
4.57
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CDBec60
CDBec60
13 Followers

After that magical first evening, when I have Dennis my first blow job, things were great. I became the woman I felt inside whenever around the house. Since I was not working, I did the cooking, cleaning, laundry, and all sorts of "wifey" duties. I was still so enthralled with being able to be a woman that I had endless energy when dressed. Because of this, I was able to prance around the house, dressed in various reveling maid outfits that Dennis started to buy me. Satin and lace. Showing off my slightly rounded butt in beautiful, ruffled panties. All while wearing stockings with a garter belt and 3 inch heels. The sexual energy my outfits produced made cleaning and cooking mandatory, as a way to work off this energy while Dennis was at work.

Sex with Dennis had not gone according to plan so far. I have always fantasized about a man fucking me in the ass. My anus tingles with the thought even now. However, I was a virgin and anal sex (as we found out) is not for the ill-informed.

That next night, I got especially dolled up. I set my hair in curlers earlier in the day, so that my strawberry blond hair was now in little ringlets. First, I gave myself four enemas to clean out my little boi pussy. I then scrapped every bit of unwanted hair from my body, showered, and rubbed in a conditioner, to give my body a smooth shiny look. After making up my face, I donned a red satin bra, panty, and garter belt set, that was decorated with black lace and strategically placed little pink silk flowers. Hoop earrings, two gold chain necklaces, long black silk opera gloves, and a black silk wrap around shortie robe to allow Dennis to unwrap his gift. Finally, my black 3 inch pumps to elongate and feminize my legs.

I dabbled a tiny amount of perfume and waited for Dennis to arrive home.

When he got home, he saw I had cooked him a dinner of oysters, asparagus, with a strawberry and watermelon salad. Followed by a chocolate tart for dessert. This was every aphrodisiac I could think of.

Dennis definitely knew what I was thinking about and told me he had been thinking about shoving his cock up my ass all day. I could tell by his squirming at the dinner table, he had a raging hard on.

The meal was finally done and Dennis got up, walked over to me, took me by the hand and led me to our bedroom. I lay down seductively on the bed while he turned on some sensuous music.

He walked up to the bedside. I got to my knees and started to unbuckle his pants while he took off his shirt. Without a word being said, his rock-hard cock sprung out of his underwear. I started lightly running my silken gloved hands over his cock and balls. He started to moan with pleasure. When I kissed the head of his penis, he shuddered with delight and let out a squeal. I pulled my face away (but kept a hand on his cock) and said "No, no, no. You are not coming quickly. Tonight is going to be special. I hope you have the energy."

With that I wrapped by lips around his hard cock and started to such lightly. I was actually amazed at myself for being such a good cock sucker. I have owned a cock for 25 years and know what I liked, but I had never even touched another man's penis before last night. But I seemed to have a knack for this as Dennis' legs were starting to shake.

I stopped with the sucking and gently guided him to the bed. He lay on his back while I was on all fours above him. I removed my robe, exposing all my lovely silken undies. I then proceeded to continue sucking and licking his cock, all the while thrusting my panty clad ass in the air, aching for something to scratch the itch I felt inside my rectum.

After a few minutes of delightfully playing with his throbbing cock, I finally whispered to him "Are you ready to take me, big man?"

"God yes!" he blurted out. He suddenly jumped up, grabbed me by the upper arms and flipped me around so that I was now lying on my back and he was on top. I started wiggling my ass in an inviting way. May anus was just itching to be opened. My rectum just itching to be filled with cock.

I lifted my legs as high as I could, revealing my panty cover asshole to him. Dennis pulled my panties to the side, placed the tip of his dick against my asshole and gently began to push.

What started as heavenly bliss, suddenly became quit painful.

"Wait, wait" I yelped "that really hurts."

"Oh, I am so sorry Janice. The last thing I ever want to do is hurt you." He seemed confused on what to do next.

"How about you just use your fingers for a while" I purred. "That will let me loosen up a bit."

Now truth be told, while I was a virgin with men, I had been shoving various long hard thin things up my ass for as long as I could remember. But they had all be relatively small and thin, such as magic marker and even the occasional hot dog. But Dennis' penis was by far twice the size of anything that had ever been there before.

So Dennis sucked his finger to moisten it and gently worked it inside my anus. He wiggled it around and at several points found my prostate. I could tell because the world melted away in a tidal wave of pleasure. I think he actually thought he hurt me because each time I would let out a little yelp of intense pleasure. After a few minutes of this, I realize my cock was getting hard. I did not want to turn Dennis off with my sudden expression of masculinity, so I slowly turned onto my side. Once there, I pulled away from his finger and turned towards him. He was kneeling on the bed with his cock still standing straight out. You could have hung a coat on it.

I wiggled my way closer and took his cock back into my mouth. I started sucking while moving my head up and down his shaft (or actually towards and away from him in that position). I began to suck harder and ran my tongue under his shaft while it was in his mouth.

Dennis leaned forward and gently pushed his finger back into my asshole. While I was sucking his cock, he was swirling his finger around inside my butt, sending the most fabulous waves of please up from my ass. This combined with the feeling of his cock in my mouth and throat as well as the thought that struck me, that I was laying on a bed, in beautiful lingerie, with a man's figure up my ass as I sucked on his cock, began to send me into a sexual bliss I had never known before. I felt so feminine at that moment, that the feelings all came together and the next thing I know, I am shuddering with ecstasy and joy. I realized I was having an orgasm even though my penis was out of the picture. No seaman came out of me, but I just knew that I was orgasming none the less.

After what seemed like an hour of overwhelming bliss, I kind of came out of the fog and realized I still had a cock in my mouth. I attached his cock like a wild woman, sucking, licking, and stroking until I felt Dennis shudder and that wonderous gush of gooey cum shot into my mouth and down my throat. I keep sucking on his cock until it began to go flaccid.

Dennis dropped down beside me in the bed and grabbed me in his arms. I lay my head on his chest and smiled like I had never been happy before.

"I guess we will have to take it a bit slower with your tight little ass." He whispered.

"I am sorry" I mewed. " I wanted to take it all. I just couldn't."

"Hey, this gives us something to look forward to. I will have to get some toys to help you loosen up a bit."

"That could be fun in itself." I said. "Me and my ass are looking forward to it."

I giggled and snuggled up to him, kissed his chest and realized I could not stop smiling.

CDBec60
CDBec60
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5 Comments
lacychristinelacychristine7 months ago

This story line is so sweet! I love the romance and the attention to the pleasure they are feeling. I love the lingerie Janice is wearing.

Put her in some beautiful, feminine dresses and make her elegant sometime. Cover her in flowy lace nightgowns, and have more romantic sex!

AnonymousAnonymous7 months ago

Janice is going to need Lube and a Butt Plug starter set and maybe a cock shaped Butt Plug bigger than you've used in the past yet a size smaller than lover boy and wear it during the day while he is away. To get used to the size. Just some suggestions Janice. 4 Stars

AnonymousAnonymous7 months ago

JANICE NO NOT A HOTDOG!!!!

also babe.... lube

rmac1rmac17 months ago

You need an editor. Too many misused words and misspelled words

chris2kchris2k7 months ago

Great chapter

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