A Wild Birthday Month Ch. 03

Story Info
David's birthday gift gives him his first taste of anal sex.
8.2k words
4.52
57.3k
11

Part 3 of the 5 part series

Updated 09/22/2022
Created 07/23/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Rave303
Rave303
78 Followers

DISCLAIMER: The story you are about to read is purely fictional. Any possible similarities between the characters and events with people in real life are purely coincidental.

**************

Ah Tuesday. Seems like nowadays the days are much happier than they used to. I was walking my usual route to have lunch with my best friend Robert, but I felt like I was on top of the world. Come on now, if you just had the Saturday night I just had, wouldn't you be happy?

If you don't know why I'm so cheery, then you might want to read the previous chapter of this story. As what's apparently becoming a month-long thing, my best friend (who happens to be very rich) bought me a threesome with two beautiful and busty escorts from one of those high-priced agencies. A week before that it was a cute blonde who was as sexy as she was sweet. You'll have to go all the way to the beginning of this tale to understand why my friend Robert bought me what looked like two incredible nights of sexual fantasy.

So it's around 1:15 PM now, and I'm walking up the street to the high-rise Robert owns to have the usual weekly lunch meetup we have. It's a little later than normal because he had to hold an online meeting with business colleagues during our normal lunch hour. I don't mind though, since I'm not in a job that requires me to clock-in and clock-out like a normal laborer.

Up the elevator I went to the penthouse office Robert has, where his lovely executive assistant Jacqueline will hopefully be there with that smile that could brighten up any cloudy day. Hopefully she wasn't out to lunch.

The elevator door opened and I didn't see sunshine, but moon. Two moons to be exact. Slightly bent over and digging through a file case was Jacqueline, only not in her usual business attire. I was witness to a beautiful heart-shaped ass clad in spandex capris.

Jacqueline: "Be with you in just a minute!"

She didn't look to see who was here, as she's feverously digging in the files. I took a moment to admire her beautiful derriere in those fitted spandex pants. I guess she must go work out during her lunch break.

Feeling daring and naughty after the porn fantasy I just experienced, I decided to play a little joke. I walked over to the window and turned to face it, my back was now to Jacqueline's across the room.

David: "Now that's a lovely view."

I didn't see what happened next, but all I heard was what sounded like Jacqui probably quickly turning around wondering what office pervert was possibly checking her out.

Jacqueline: "Excuse me? Oh, David. Hi!"

I turned around and smiled.

David: "Hey Jacqui. Was just admiring the view out your window here."

Jacqueline: "Really...and here I thought it was Andy the office pervert trying to sneak a peek at me in my workout gear."

Now I could see what Jacqueline was wearing. Spandex capris with an athletic top that showed her pert breasts quite nicely. Athletic socks and gym shoes were on her feet and she had hair tied off. She did look like she had been sweating.

David: "You look great."

Jacqueline: "Oh gawd I so do not."

David: "Not from where I'm standing. You look like you're in incredible shape."

Jacqueline: "You flatterer. Spin classes and Pilates do wonders."

David: "It shows. Robert doesn't mind you in that attire?"

Jacqueline: "I'm sure Robert would rather I work in a bikini if he could pull it off. He actually lets me use the executive bathroom to shower and change when I go work out. I just came back from the gym though and Robert needed some files ASAP. Come on, let's go see him."

Jacqueline took the lead as we headed over to the doors to Robert's large office. I did take a moment to savor Jacqueline's sexy body as she moved in front of me. I'm thankful I just had the weekend I did, or else I probably would have been hard as a redwood the moment I saw Jacqui. I kept thinking about how much I would love to date her, and decided I'm going to take a chance and ask Robert if he would have a problem with it.

We entered Robert's office and he was just finishing up a phone call. He waved us over before saying "bye" to whoever he was talking to and hanging up, Jacqueline walked over and placed a stack of files on his desk.

Jacqueline: "Here are the files on Merck."

Robert: "Perfect. Thanks for the rush sweetie."

Jacqueline: "I'm going to go shower and change. I'll be back at my desk in 15 minutes."

Robert: "No problem. Don't forget behind your ears."

Jacqueline rolled her eyes and giggled a little bit before looking at me with that beautiful smile.

Jacqueline: "See you later David."

David: "Bye Jacqui."

Jacqueline made her way to the door and closed it behind her.

Robert: "Mmmmmm...I hate seeing her go, but I love watching her leave. It's a shame she's my employee."

David: "I'm surprised you haven't gone further. You were always the ladies man."

Robert: "Nah, not with Jacqui. I don't play with my employees. Plus I respect her too much to treat her like a hookup. Besides, she just dumped some loser who cheated on her."

David: "She hides it well."

Robert: "Yeah, they didn't go out long. When I found out about her dumping him I ended up having my lawyer call that loser and put a huge scare into him. Made it sound like she was a mafia don's daughter. The guy must have shit his pants."

We both laughed. I'll give Robert credit. He might be a player with the ladies, but he's still got a heart. I remember one time he got into a fling with a fashion model who wanted him to commit. When things turned ugly, he simply wheeled and dealed and got her on the cover of Vogue as a way of saying "No hard feelings."

David: "So you wouldn't touch Jacqui...what about if I wanted to?"

Robert looked at me for a moment in surprise and concern.

Robert: "What? You want to fuck my assistant? Your birthday gift isn't enough?"

David: "Well, yeah. Fuck...but also date, dinners, movies, shows, walks in the park, fall in love, happily ever after, etc. Would you have a problem if I asked Jacqueline out on a date?"

Robert's face of concern turned into a smile.

Robert: "Of course I have no problem. Jacqui's a prime piece of real estate and I can't fathom a better guy for her."

David: "Thanks Robert. I didn't want to step on any toes or anything. Through thick and thin you've always been a good friend."

Robert: "No worries. I just have two requests."

David: "Go ahead."

Robert: "One, if you break her heart I will bury you alive."

David: "Whoah..."

Robert: "Two, you wait until after your birthday to take her out. I've spent plenty of money on this gift and I don't want that coming into the mix with Jacqui. It's only two weeks left and I can see a little sexual healing has done wonders. Look at you. You've been coming in here smiling at Jacqui every week for a year since I hired her. Bout time you got your balls back."

David: "I hope I can survive with my balls after the next two weeks. You hungry?"

Robert: "Definitely. Where do you wanna go?"

David: "Let's hit up O'Donnell's Irish Pub for a beer and some of those famous burgers they push."

Robert: "Whoah...a beer during work hours? Who are you and what have you done with David?"

David: "Let's just say I buried him alive and I'm going to be a new David from now on."

We left for O'Donnell's as Jacqui was somewhere probably showering that sexy body and changing for the rest of her workday. I was thrilled inside to find out not only is she single, but I have Robert's blessing. It's too bad I have to wait two weeks.

Robert and I had burgers and beers while I filled him in on the threesome. I tried to get an idea of what he had in store for me this weekend, but he wouldn't budge and simply told me I'd have to wait and see.

I ended up working a little later that Tuesday since Robert and I took a long late lunch. The rest of my week came and went without a hitch. So here I am on Saturday, expecting something sexual to come knocking on my door for another wild night. This time though I'll try to be better prepared. I picked up a few bottles of wine at the store to serve to whoever comes, and cleaned up my house. Sometimes I think I should hire a cleaning lady with all the work cleaning this big house entails.

I figure the woman or women coming will probably be here at 8, since Ashley, Elena, and Sarah all came around 8 in the last two weeks. It was 6PM and I determined I had time to get a workout in, then shower and be ready by 8. I went up to the bedroom and picked out a shirt to wear later, laying it on the chair. I changed into my workout clothes and went to the small gym setup I made in the basement.

I figured a workout would make me loose but energetic to handle whatever Robert had in store for me. I did thirty minutes of free weights and then spent thirty minutes on the elliptical, building up a lot of sweat. I kept wondering what Robert had in store for me, and was a little excited at the mystery. I also kept thinking about Jacqueline today, thinking how much better it would be if she ended up at my door tonight.

"DING DONG!"

David: "Shit!"

I looked at my watch and it was nearly 7. Crap...she was earlier than the others were, and here I was a sweaty mess in my workout clothes. I was embarrassed, but had no choice. She would think I blew her off if I ran to get a shower and change before answering the door.

I thought maybe I could apologize for my appearance and offer her a glass of wine while I cleaned up. I opened the door and saw only one woman there. I will say while last week was fun, it is a lot of work to please two girls at one time. One on one is more my speed.

The girl herself must have been 5'7" with the black heels she had on. She was clad in a gray baby-t and denim shorts, and had a very European looking face. Definitely Eastern Bloc or maybe Mediterranean. Her shoulder-length black wavy hair was tied off and she had a basket of what looked like cleaning supplies.

David: "Yes?"

Zhanna: "My name is Zhanna. I come to clean house, yes?"

Zhanna spoke broken English with a thick accent. Wasn't sure what country because I'm not good at identifying those things. I almost wondered if Robert was a psychic since I was contemplating paying someone to clean my house, although in 4" heels I don't think Zhanna was here to clean.

David: "Come in."

Zhanna came in with the clacking of her shoes echoing in the living room. She looked around and I got a chance to look her over. She had decent looking tits, proportional to her body, but her ass...wow. Heart-shaped like Jacqueline's. It just bubbled and bulged out there like ripe fruit. I started to get lost in Zhanna's nicely shaped derriere when she turned and spoke to me.

Zhanna: "This house clean already."

David: "Well, yeah. I cleaned it earlier. I didn't expect anyone to come here to clean my house."

Zhanna got a good look at my messy self though. I was covered in sweat, and my hair was a mess.

Zhanna: "Look at you. You a mess. Come, I clean you up now."

David: "Oh, you don't have to do that. I can get you something to drink and I'll go take a quick shower."

Zhanna: "No! You a mess and I clean you up. Go before you make mess of house."

With her basket in hand, Zhanna started pushing me to go upstairs. She must have spotted the guest bathroom right near the top of the stairs and pushed me towards it.

David: "But that's the..."

Zhanna: "MOVE! Get those things off!"

This girl was definitely different. Ashley, Elena, and Sarah were more tender and playful. This one was just forceful. I hoped Robert didn't get me some dominatrix type. I am so not into that. I wonder if he is?

I kicked off my shoes and removed my t-shirt. I caught Zhanna licking her lips out of the corner of my eye, which made me feel like a champion. I then slid my shorts off to reveal my half-hard cock

Zhanna tossed the clothes into a nearby hamper and then opened the door to the shower. While the master bathroom in my bedroom has a nice shower and hot tub, this guest bathroom is tiny. Just a toilet, sink, and a shower stall. Not even a bathtub. Zhanna then turned on the water to a semi-hot temperature and gently pushed me in. I then watched as she kicked off her heels and removed her tank top to reveal a royal blue string bikini top with yellow trim. She then unbuttoned her denim shorts and pulled them off to reveal matching bikini bottoms.

I'll admit I liked what I saw. The bikini showed off her sexy curves and I could only wonder how much fun I'll have playing with Miss Zhanna tonight.

Grabbing some stuff from her basket, Zhanna came into the stall with me and closed the door. It was a bit cramped with the two of us here, but I wasn't complaining. She had a sponge and what looked like some body wash. My cleaning lady started rubbing lather into my skin and worked her sponge all over the upper half of my body, even turning me around to wash my back.

Zhanna then rinsed me off and put more wash on her sponge, squatting down to lather up my legs and crotch. It felt great to get cleaned up like this, even though nothing very "sexual" had happened yet.

Water cascaded down my body as soap suds washed away. Zhanna was still squatting as she wiped the remaining suds off. I could feel her hands occasionally brush my cock as it hardened up in front of her. She was teasing me a little with this shower, but not anymore.

Zhanna: "Now you are clean. We get dirty again."

Zhanna, still squatting, took my hard cock into her mouth and began to suck on it with a loud "MMmmmmmm". I let out a sigh and leaned back against the wall. She wasn't the best head I ever got, but she felt wonderful as she sucked on my big man and bobbed her head in and out for a bit.

After a few minutes of blowing me, she then took my cock out of her mouth and began stroking it. I even felt her put some kind of lube on as she thoroughly rubbed my cock in and out with her hands. I guess she was going to give me a nice hand job as an appetizer.

Little did I know that Zhanna had pulled aside her bikini bottom, exposing her pussy. I had closed my eyes and enjoyed the sensation of Zhanna's lubed hands rubbing my hardness. Suddenly, she stood up.

Zhanna: "Now you will fuck me."

I was always happy to oblige, and I got a kick out of how Zhanna was very direct in what she wanted. I wasn't sure if she wanted to fuck me here or someplace else, but I decided I'd just follow her lead.

What she did next shocked me. Before I even had a chance to react (or even think), Zhanna turned around with that beautiful heart-shaped ass to me, bent forward a bit, and pressed my cockhead at her anal opening. She pushed back a bit and the head of my big man popped into her anus.

David: "Whoah!"

Zhanna: "Oh yeeesss!"

Zhanna then slowly pushed her self back, impaling her sexy ass on my cock. I was in total shock and surprise since I never had anal sex with any woman in my life.

David: "HOLY SHIT!"

Before I knew it, Zhanna's pretty butt was resting against my body. Her bikini bottom pulled to the side, crossing over one of her curvy butt cheeks.

David: "No condom needed here?"

Zhanna: "No. I just get over yeast infection. My pussy sensitive, so you fuck my ass, yes?"

Zhanna pulled a bit forward and part of my cock came out. I thankfully didn't see any brown on it, which told me this was planned and she was sent to let me experience anal sex. Wow Robert, very nice.

I went to try to move us, since I didn't think I could get good movement in that stall.

David: "if you want, we could move to..."

Before I could finish, Zhanna forcefully pushed herself back, pinning me to the wall with her sexy body.

Zhanna: "No. We fuck here first."

Zhanna started to rub, grind, and rotate her sexy ass on my body. My cock buried to the hilt in her anal opening. I was in awe as she spoke dirty to me.

Zhanna: "We fuck in here and in the bedroom and the kitchen and everywhere in the house tonight, yes? You fuck my ass over and over and cum inside me, yes?"

I couldn't say anything that would matter. I was trapped between the wall and Zhanna's round ass as I felt my cock rooting around inside her anus. I could feel her sphincter clenching itself tightly around my big man like a vice. Anal sex definitely felt different than intercourse in a vagina.

Zhanna then began to pull herself forward and forcefully push herself back on me, fucking me with her ass. Every time she pushed back, it pinned me in there, trapped and forced to simply enjoy the bounty this European tiger offered. She continued to pump my cock over and over with her ass and clenched her butt cheeks at times to further drive me insane. Zhanna loudly moaned and breathed heavily with each push that my cock drove deep into her.

My wild cleaning lady started to pick up the pace, slapping her butt on my body as her ass continued to stroke my excited cock inside her. I could feel my first climax building up.

David: "Zhanna, I'm going to cum for you."

Zhanna: "Ohhhyesss. Cum in my ass!"

Zhanna then went faster, slamming her ass on me. I can tell this isn't the first time she's done this, and I'm honored to be a notch on her belt. The lube on my cock combined with her tight anal opening and movements was all that I could handle. I grabbed Zhanna by her hips and pulled her into me hard as I let out a grunt and fired load after load of my cum into her hungry ass. It almost felt like her butt was sucking it right out of my manhood.

She moaned and screamed as she felt my cock empty itself into her, goading me on to finish. We stood there for a moment as I panted at the shock my system took, but then Zhanna slowly moved forward and let my softening cock come out of her.

David: "Ohmygawd...I've never done that before!"

Zhanna: "First time for everything, yes?"

I smiled as Zhanna then took her soapy sponge and washed off my now limp cock. I could see my own cum washing away down the drain as it was oozing out of her ass. After rinsing me off, she turned off the shower, grabbed some towels, and dried me off before drying herself off. Zhanna straightened up her bikini bottom before sliding her feet back into her high-heeled shoes.

Zhanna: "Now we move to next room, yes?"

David: "I'm all yours."

Zhanna took my hand and led my naked self out of the guest bathroom. I saw the master bedroom down the end of the hall, but my home office caught her eye.

Zhanna: "We go here now."

My home office isn't anything you would not expect. I had a nice oak desk with my laptop on it and an executive chair as well as a smaller flat screen TV and stereo. Along the wall opposite to the stereo and TV was a black leather couch.

Zhanna pushed me down into a seated position on the couch and then sat next to me. She pulled the scrunchie out of her hair and let it all hang loose. She wasn't as stunning as Sarah or especially Jacqueline, but I will admit she was a sexy beast with her own unique vibe.

She started to massage my limp cock and asked: "And how is our little man?"

David: "Still in shock, but he'll eventually be ready for more."

Zhanna: "I help him get ready, yes? I want to dance. You sit and watch."

Zhanna rose up from the seat and slowly walked her way over to the stereo. I couldn't take my eyes off her beautiful ass as she sauntered over and began to look for some music to play. She eventually settled on some kind of deep sexy soulful jazz/electronic music hybrid CD I had.

Rave303
Rave303
78 Followers