A Wild Birthday Month Ch. 02

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David receives the gift of two busty escorts.
6.6k words
4.62
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Part 2 of the 5 part series

Updated 09/22/2022
Created 07/23/2011
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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.

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It's 11:30 AM on a Tuesday and I'm on my way over for my weekly lunch meetup with my childhood friend Robert. Unlike other weeks, this one is different. In case you didn't see the first part of this story, I'll be brief. Two years ago I was humiliated when I saw my wife of eleven years on a tabloid celebrity TV show...in another country with some wealthy playboy. She had apparently been having an affair with him for a year.

Divorced and humiliated, I spent the following year and a half sulking, hiding in my work and in my big home I originally planned on having a family in. My childhood friend Robert is also another wealthy playboy who did well in the stock market. He wasn't the guy who stole my wife, but he accidentally caused my wife to meet the guy she ended up running away with.

Ridden with guilt, Robert always felt obligated to make it up to me, but I kept telling him it wasn't his fault. Worried about me spending another birthday alone in my home, he ended up surprising and shocking me with a unique gift -- an entire evening with a beautiful and highly paid escort. I originally was reluctant, but Ashley (the escort) helped me break out of my shell and gave me one night of mind-blowing sex I'll never forget.

So this week it's different. I wasn't feeling down on my life anymore. I wasn't feeling inadequate. I felt like I had a new lease on life, like a massive weight was lifted off my shoulders. I strolled up the street from my work to the high-rise that houses Robert's multi-billion dollar business, took the elevator up to the top, and of course was greeted by his lovely executive assistant Jacqueline.

Jacqueline: "Hi David!"

I don't know what it is, but that gleaming smile from Jacqueline just brightened up my day even more. She's as sweet and smart as she is pretty. Ever since that wild night, I had contemplated asking her out on a date, but I still think Robert might have a problem with me messing with his assistant.

David: "Hey Jacqueline. You look great today."

Jacqueline: "Why thank you. You seem different today."

Well, I couldn't help the compliment. Jacqueline was wearing one of those business suits for women that most guys drool over. Her long dark hair flowing over her shoulders and sparkling brown eyes could mesmerize any man. Even with her glasses on she just screamed smart and sexy. Maybe I just feel more daring today since I got some of my masculinity back.

David: "I don't know Jacqui. I just feel like I got a new lease on life. Just had a wonderful weekend."

Jacqueline: "Well, that's nice to hear. What did you..."


Suddenly her phone rang. She answered and all I heard was "Yes Robert." and "OK". She hung up the phone, smiled and told me Robert would see me now. I guess I was saved by the bell since I don't think I want to tell her I was nailing a highly-paid escort.

David: "I'll see you later Jacqui. Nice chatting with you as always."

Jacqueline: "See you later David."

I strolled into Robert's office, closing the door behind me. Sitting behind his desk was Robert with a big smirk on his face. I looked at him with a sarcastic look of disgust.

David: "You're an ass."

Robert laughed. "Look at you. Look what one night of good sex can do. You even dressed differently. Every week it's the same shirt with a tie and slacks. Now today you're not even wearing a tie."

David: "Yeah, I'll admit you were right."

Robert: "Told ya. Come on, I want sushi today. You're buying."

We left the office with Jacqueline and I sharing a smile as I walked out. My mind wandered a bit if I should talk to Robert about the possibility of asking her out or not, but I know Robert is a bit possessive on things, including his staff. I can't imagine him liking the idea of someone trying for his assistant. Plus, how do I even know if she's single? A girl like that has to have a boyfriend or husband.

I cleared my mind as Robert and I got a table at a nice sushi parlor we like. After the waitress took our order and left us alone, the questions came out.

Robert: "So how was she?"

David: "I'll be honest, she was incredible. I never had sex like that in my life. Not even with the ex."

Robert: "I saw Ashley's photos. She's got a hell of an ass. Did you get to tap that?"

David: "Well, I'm not one to kiss and tell..."

Robert: "BULLSHIT! Speak...since I paid good money for her."

David: "Well, Ashley doesn't allow guys to do anal on her. She was amazing, especially when she gives head."

Robert: "No anal? Oh well, she's hot anyway. Not very 'endowed' when it comes to tits though."

David: "Yeah, but I didn't mind. Her talents more than made up for that, although I might have to seek out a girl with a nice rack when I get back in the game. I honestly wouldn't mind sex with a girl who has a great pair."

Robert: "Heh...David needs some milk?"

David: "Oh...you just reminded me. I need to stop at the store on the way back. I do need milk for coffee. Thanks for the reminder."

Robert and I laughed and talked like we usually do. I was thinking of asking him about Jacqueline, but I held back. I even wanted to inquire why he sent Ashley to me weeks before my birthday, but I decided to stop looking a gift horse in the mouth.

Lunch ended, I got my milk, we parted ways, and I went about my week. Saturday hit and I did my usual regimen of relaxation, housework, and exercise. With all the domestic stuff finished, I decided to pull up a movie on Netflix and have a beer.

With Bruce Willis shooting terrorists on the screen, my mind went back to Jacqueline. I kept wondering if Robert would have a problem, and would she even go out with me. Forgive me if I sound insecure, but not all the wounds of the past have healed, and Ashley did help get the healing process rolling better. Maybe I should try a dating site instead, rather than putting all my eggs in the basket of the first woman I get eyes for.

"DING DONG!"

My doorbell rang, and thus interrupted my thought train. I hopped off the sofa wondering who this was. As I approached the door I was hit by a thought as to why Robert sent Ashley to me three weeks before my birthday. Perhaps Ashley isn't the only one he hired.

I opened the door and before me was not one, but two lovely ladies.

David: "Well hello ladies."

Sarah: "Hi. Are you David?"

David: "Since I was born. And you are?"

Sarah: "My name is Sarah, and this is Elena. We heard from Robert you like milk. May we come in?"

My eyes first locked on to Sarah. She was gorgeous. Probably about 5'10" with the black heels she was wearing. She was clad in what could only be described as a sexy milkmaid outfit. Some kind of farm girl ruffled top and short fluffy skirt, all colored with a white and red checker pattern you normally expect on a picnic tablecloth. Her long light brown hair was tied off in two unbraided pigtails, each with a matching red ribbon.

Sarah had a stunning face I had to admit. She had beautiful green eyes that shimmered like gems with high cheekbones and a smile that would melt any man. I would guess her ethnicity was Czech or some Eastern Bloc country, despite that she had no accent. Regardless, I wondered why she was a high-priced escort. She could walk the runway for Victoria's Secret or be some millionaire's trophy wife.

Elena was Latina, and a beautiful one at that. The best way to describe her would be Vida Guerra's lost sister. She had dark skin and long dark wavy hair with some very sexy Spanish curves. Elena was clad in an outfit that I could best describe as "inspired" by the typical Hooters waitress outfit. She had on white high heels as opposed to sneakers and socks, shiny purple shorts that accented her delicious bubble butt, and a black tank top with "got milk?" printed on it.

I almost forgot to mention the best part. Outside of Sarah's stunning face, Elena's exotic looks, and their outfits, both women were very well "endowed". Sarah must have had full D-cup breasts filling out that milkmaid top of hers, and Elena...wow. She must have been a double-D cup size as the "got milk?" text was pushed out nicely. I'm surprised that tank top made it all the way here without bursting open.

I didn't even care if their tits were fake or real. I knew I was in for an amazing night not only fulfilling my bit tit fantasy, but a threesome. What a birthday gift! I get to live out every porn fantasy most men have ever dreamed of.

I let the girls come inside and closed the door. Sarah then handed me a glass bottle of milk.

David: "Why thank you."

Sarah: "We heard you needed milk. Is skim ok?"

I decided to be flirty. "Well, I normally like things nonfat, but I also usually get some half-and-half as well."

Yeah, I know it sounded cheesy, but I do generally keep half-and-half for coffee. Elena then took my hand and brought it to her left breast.

Elena: "I think we could accommodate that. Sarah knows how to milk the right stuff out of someone, and I just give service with a smile."

Sarah: "I'll take care of this."

Sarah took the milk bottle from my hand and walked over to the kitchen to put it in the fridge. I took the moment to feel over Elena's gigantic breasts. They were soft, squishy, but firm. My cock grew in my pants rather quickly.

As Sarah walked back towards us, I saw her reach behind her back and pull on some strings, apparently undoing her top. Elena moved her hands down to the bottom of her tank top and began lifting it as well. In a few swoops, Elena and Sarah removed their tops, showing me their bare and beautiful breasts. I have a feeling they were originally decent in size, but each had enhancement done. Their racks looked like solid expensive work. No "refund gap" or odd hanging. Just big and bold, sitting there like they were teenagers. Some might still question if these girls were just well endowed but I wasn't going to dwell on it.

I went back to fondling Elena's bare boob while Sarah brought my other hand to one of hers. If my cock could speak, it would have been screaming to be let out. I took my time though and fondled their boobs for a minute or two, feeling their large nipples grow hard to my touch.

Elena then placed her hand on my crotch and began to rub my big man.

Elena: "What do we have here?"

Sarah then took a feel of my hardness with her dainty hand.

Sarah: "Looks like an udder for me to pull and squeeze on. Shall we take this someplace more comfortable so I can milk this little guy over and over?"

David: "Right this way ladies."

Elena grabbed her somewhat large purse and took my hand as I took Sarah's hand and led them both upstairs to the master bedroom. When we arrived, Elena dropped her bag and then both girls proceeded to undress me. Thankfully I was just dressed in my usual house clothing of athletic pants and a t-shirt.

Tossing my clothing on a nearby chair, the girls smiled and pushed me down onto my bed with my legs handing over the side. They then proceeded to remove the bottom halves of their costumes, revealing some skimpy thongs they had on underneath. Elena then was about to remove her shoes when I spoke up.

David: "Ladies...would it be too much trouble to leave your heels on?"

Sarah: "You want shoes on the bed? We don't want to mess up your linens."

David: "Yeah, I know it might sound ridiculous, but I guess I just wanted that total fantasy of two beautiful women doing me in high heels like you see in the porn films. Probably sounds lame."

Elena: "Not at all. It's a fantasy many men have. We'll leave them on for a bit."

David: "Thank you. Feel free to take them off if it gets uncomfortable."

So now I was lying naked on my bed with two beautiful women clad only in high heels and thongs, each with massive breasts to my pleasure. I wanted my porn fantasy all the way so I'll remember it as long as I live. The cost of getting the linens cleaned would be so worth it.

Sarah and Elena crawled up next to me on either side. I wasn't sure if I get the "full experience" again, but I moved to kiss Elena first. She welcomed my mouth as we started to make out, my one hand under her and the other massaging one of her massive melons.

Sarah started kissing my shoulder and the back of my neck, caressing my skin but not touching my cock just yet. Not wanting her to feel left out, I broke my kiss with Elena and moved to do the same to Sarah. Our lips locked and our tongues caressed one another as I played with her big breasts. Elena started to kiss her way down my body and made her way to my cock. She started to plant little kisses on it, making my skin tingle with excitement.

Meanwhile, I broke my kiss with Sarah and proceeded to start nibbling on her massive tits while sliding my hand down South. I first gently caressed her pussy through her thong, but after a minute I slid my hand inside. She was hot and wet and sighed to my touch. I rubbed her pussy gently as my lips gave extra attention to her beautiful breasts.

While pleasuring Sarah, Elena took my cock in her hands and began to slowly lick it from base to head. I tried to pay attention more to Sarah simply because I didn't want to explode that very second to Elena's touch, but it was hard. Elena took my cock in her mouth and slowly went down inch by inch until I could feel the head in the back of her throat.

Elena began to slowly move up and down my cock, resting her arms on my thighs while kneeling on the floor just off my bed (I did mention my legs were hanging off the bed). Her tongue felt silky and velvety as she sucked on my cock and continued to please me with her mouth.

Sarah on the other hand was enjoying me rubbing her clitoris as we returned to making out. After a few minutes of this, she broke our kiss and slid down to join Elena.

Elena: "Want some? I don't think I'm milking this right."

Sarah: "Why don't you go sit with David and I'll show you the proper way to milk this udder."

Elena smiled and crawled up next to me. We first watched Sarah as she gently stroked me.

Sarah: "The simple way is by gently pulling, tugging, and stroking."

Sarah then put her other hand on my balls and started to massage them. I was in heaven.

Sarah: "Sometimes you have to stimulate things a little more. However, I like using my mouth to better stimulate the milking process."

Sarah then put my cock in her mouth and started to suck and bob up and down. At this point I thought I would explode immediately but Elena saved me by bringing her lips to mine again. We kissed deeply and I continued to pleasure Elena just as I did Sarah, sucking on her massive tits and playing with her wet pussy through her thong. Elena was moaning and loving every moment of it as Sarah began a faster pace while massaging my balls.

Finally, Elena pushed me away and climbed on top of me in a sixty-nine position. Pushing her thong-encased pussy in my face, she proceeded to take turns sucking my cock with Sarah. Every time Elena bobbed her head up and down on my cock for a bit, Sarah went to sucking and licking my balls.

There's only so much a man can take. I tried to tell them I was going to cum, but Elena simply pushed her pussy back into my face, grinding her sexuality on me. Finally she pulled my cock out of her mouth and rapidly stroked it as she and Sarah awaited the prize.

I couldn't take anymore. I exploded as Elena kept moving my cock back and forth, shooting some cum into Sarah's mouth and then into her mouth. I was just lost in silk enhanced with the smell of sweet Spanish pussy, breathing rapidly at the orgasm I just had.

Still on top of me, Elena and Sarah commenced on gently cleaning my cock lightly with their tongues. My little guy was hypersensitive to their touch, but they continued until he was clean as a whistle. Elena climbed off me and asked if she and Sarah could clean up a tiny bit. Apparently I did get one or two shots on their faces as opposed to their mouths.

I directed them to the bathroom and asked if they wanted any wine or something to drink. The girls said wine sounded good, so I went downstairs to open a bottle of Pinot and grab three glasses. I was hoping I could last more tonight so I could get more and more of these busty beauties.

When I arrived back in the room, the two were sprawled on the bed in a seductive fashion, still clad in their thongs and high heels.

David: "Now this is a beautiful picture."

They giggled as I handed them glasses and poured them wine. We sat for a few minutes, drank, and even fooled around a little. Elena would pour some wine on her skin and I would lick it off. Sarah also licked some wine off Elena for fun.

Eventually, Sarah started caressing my cock wanting to get me hard again for more action. Elena joined in as they took turns lightly giving me oral and playing with my balls while the other would make out with me and let me play with their tits. After a little while, my cock was beginning to grow again and I had an erection...feeling like I could go into the night.

Elena: "Got milk?"

David: "Um...just downstairs in the fridge. You two seemingly have all the milk here."

I lightly fondled one of Elena's breasts.

Elena then said, "Want milk?" as she shook her chest a little bit, her big breasts bouncing at her movements. Sarah giggled.

David: "Ok. What do you have in mind?"

Sarah pulled me off the bed and sat me down in the chair the girls tossed my clothes into. Elena went into her bag that she brought and pulled out what looking like a bottle of oil. She poured some into her hands and began to massage it into Sarah's breasts, making them all shiny. Sarah then poured some into her hands and did the same on Elena.

The two walked over and knelt on the floor in front of me, taking their partially oily hands and rubbing them all over my hard cock. With a seductive look in her eye, Elena spoke again.

Elena: "Time for round two sexy. You're going to cum all over our big tits."

Elena then spread my legs more and moved in between them. Grasping her gigantic breasts she wrapped them around my cock and slowly began to stroke up and down. I was excited, as it was the first time I had ever been tit-fucked. My ex unfortunately didn't have large knockers, so we couldn't really do that.

I sat back and enjoyed the show as Elena continued to stroke my cock with her magnificent mammilla. I was happy the girls "milked" me once already, because I wanted to enjoy this.

Looking across the room, I noticed a large standing mirror my ex left when we divorced. It was a bonus now as I could see Elena's bubbly ass bounce on her high heels as she moved up and down on my cock with her tits. I didn't know where to keep my focus, but I was loving every minute of it.

After a few minutes, Elena released my cock from her warm oily tits and allowed Sarah in on the action. She smiled at me with that tender smile that I said could melt most men as she wrapped her D-cups around my cock and continued where Elena left off. Up and down she went, over and over as I switched from watching her tits around my manhood to her tight ass bouncing in the mirror.

And so this went on for a while. Each girl taking turns every few minutes. I lasted a bit longer since I will admit I didn't get as much stimulation from their tits as I would their mouths or pussies. I wasn't complaining though. I felt like a king being serviced by two slave girls, and my bodily fluids building up into another wonderful orgasm.

Rave303
Rave303
78 Followers
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