Alexandria, VA -- 1993
This was my second business trip, heading down to DC. I landed at then Washington National Airport and took a cab across the river to my hotel. I unpacked my suitcase and headed down to the hotel bar and restaurant. I was young and naive back then, ignorant to some of the realities of sex. I had not yet realized that what is pleasing to the eye, and what is pleasing to the touch are rarely the same. Truth be told, even then I had certain fetishes... older women, and chubbier women. An older woman walked in and sat next to me at the bar. She ordered a glass of wine. I sat there and ordered my steak. I finished my dinner, and the bartender asked if I wanted desert or another drink. At 23, I had champagne taste and a beer wallet, so I thought about it and said no to both.
Without looking at me, the woman next to me said to the bartender "Get him another drink and put it on my bill."
Of course, I thanked her profusely.
Again, without looking up she asked, "First business trip?"
"Second", I said, "I'm Jack.".
"Pleased to meet you."
With that she finished her meal and ordered a second glass of wine.
"I travel every week. It keeps me sane. I am not the type to stay in an office all day. And besides, I love the perks."
"Perks?" I asked.
"Yes. When you do this more, you'll understand."
"Do you mean like airline points and upgrades and free travel?"
"Yeah those are a few but I don't need them. I have plenty of money and nothing to spend it on."
"Well what other perks do you mean?"
"Jack, IF and ONLY IF you're a good boy for the remainder of the evening you may find out."
Hmmm, I wasn't really sure where this was going, but I was definitely curious. With that, she said she needed to use the ladies, and this was the first time she turned to me. She was medium height, a little on the heavy side... a smaller BBW. She looked to be 50ish. Her tits were big but not enormous... a strong D cup. Interesting thing about bigger ladies... first, though I didn't know it at the time, they universally give amazing head. I have had good head from smaller women, but I've also had some not so great head. I have never been blown by a fat girl when it was anything short of spectacular. The second thing about BBW's is how they carry themselves, and their shape. I'm not into women where in the words of Andrew Dice Clay, "you can't tell where the tits begin and the belly ends." If her belly sticks out further than her tits, it's a showstopper. This woman was the opposite. She was curvaceous. Slim but round butt, wide hips, and what appeared to be extraordinarily strong very sexy legs.
"I'm going to use the Ladies. Order me another glass of wine and another drink for yourself, on my tab. Have the bartender bring the bill as well. When I return, we will get to know each other a little better."
I did as requested, as did the bartender. Upon her return she took her seat, and we made some chit chat. Turns out she was a partner in a NYC IP law firm. Divorced, no kids, doesn't want any. While we were chatting, she kept leaning into me, showing cleavage, and would occasionally brush her leg against mine. As is typical of a 23-year-old guy, a stiff breeze gives them a hard on. I wasn't full on hard but had a semi that was getting extremely uncomfortable. I politely excused myself to go to the bathroom, take a leak and re-adjust. When I got up her eyes went right to my jeans and checked out the noticeable bulge. Upon my return, she had just finished her wine.
As I finished my drink, she said "Okay, Jack, I'll let you in on one of the perks. There are a lot of lonely people on the road. We are away from spouses, boyfriends, family. Sometimes, it's nice to have a little company."
"Okay," I said.
"So, here's the deal. This is my spare room key." She slid the key card over to me. "No pressure. If you are interested, be in my room in 20 minutes. Just let yourself in. It will be dark. Have a seat on the sofa and wait in silence. If you do that, we will be friends for the week. After that, it's no strings attached. No phone numbers, no emails, nothing. If you are not there in 20 minutes, I will have the room rekeyed, and we are done. Fair?"
"Fair", I agreed.
She looked at my bulge again and gave me a wry smile,
"I have a funny feeling you won't disappoint."
I went up to my room and took a very quick shower, dressed and looked at the key. 1220. The penthouse floor. Off I went. When exactly 20 minutes had passed, I used the key and opened the door. I started to say something, but she cut me off.
"You must be a good boy."
So as requested, I sat on the sofa. Once I was seated, she lit some candles.
The first thing she said was "Okay, the first rule is let the first one happen."
As she said this, she got on her knees in front of me, unfastened my snap and zipper and pulled my cock out through the fly in my boxers. I went instantly hard.
"You young guys are all the same. You'll be able to go 3 or 4 or 5 times in one night, but it's not fun if you keep having to stop because you're cumming. So no holding back. If you are, I will know."
With that she took my entire cock down to the base. She wasn't so much blowing me as she was getting it wet with her copious spit. Rivulets of saliva were running down my cock. Then she started in earnest. It felt amazing. I was getting close. We are not talking about minutes here. This was seconds. I tried to hold back, and she stopped.
"Remember... just let it happen, or I will make it happen".
With that she pulled down my jeans and boxers and went to work.
After about 30 seconds she said "Okay. Looks like I need to make it happen".
She licked her middle finger, and then in one motion she stuck my cock down her throat, and her finger in my ass. Then she opened her mouth and started tonguing my balls. That's it, I was done. I screamed out in surprise and pleasure as I unloaded into her throat. I have no idea how she took all of it. I cum a LOT and this felt like the biggest load I had ever produced to date. She released my cock with a slurp, and I laid back exhausted. My cock had gone down but only slightly.
"See? Now you'll last a while for me. Good boy."
I had just noticed that she had changed into a wifebeater and shorts. At this point, she mounted my left leg and put her arm around me.
She started to pull me in for a kiss and said "I think you'll find that women in their 50's are much like men in their 20's. Always horny, always wet and ready to go on a minute's notice."
With that, she pulled me in for a kiss. As we were making out like teenagers, she began grinding herself on my leg. She began to moan, her grinding getting more and more urgent. She reached down and grabbed my cock and started playing with it. After about three minutes her body tensed up and she literally shrieked like a banshee. I could feel her girl cum oozing through her shorts and on to my leg. Then she kept going. She orgasmed three more times in as many minutes. Finally, she stopped and slumped on top of my chest.
"See? Damn I love a good dry hump. When I don't find myself a cub to play with, I make an unholy mess of the pillow." With that she looked at my cock. "I see we are ready for more playtime."
With that she got on her knees in front of me. She took off the wifebeater treating me to a classic tit drop and wrapped her tits around my hard meat. She then took just the head into her mouth and used just her tongue while she massaged my shaft with her big tits. She kept working at it, keeping me lubed while varying the motions of her tongue. Before long I was thrusting up into her mouth.
"Uh uhhhh.., "she said. "You have to ask me this time. "Are you ready?"
"Yes Lorraine, I'm ready to cum!"
"Where are you going to cum?"
"Wherever you make me!"
"Excellent Jack! You're learning!"
With that she went back to her blowjob/tit job. It's interesting, I've been told by several women, not only do I cum a lot, but that it's very easy to tell when I'm about to nut. They tell me the head gets bigger, I grow about a half an inch, and I get thicker. I'm not sure if that happens to all guys, but for me it's pretty noticeable. As I got closer to the edge, feeling my balls contract and my jizz flowing into the base of my cock she started to hum. That put me over the edge. She took me out of her mouth and aimed it all over her big tits. I unloaded on her covering her chest and neck with my white-hot sperm.
"Damn nice load Jack. I know you wanted to cum in my mouth, and I love swallowing, just like I like it in my pussy, my ass, and on my ass and back, but I fucking LOVE to watch. When I watch porn I get myself off to watching big cumshots, and that one was ENORMOUS. Good Boy!" "Come, let's lay down in bed."
She turned on a light, and poured us each some water, and a glass of white wine. This was the first time I had gotten a good look at her tits. They were firm with just the right amount of sag. Her nipples weren't that long, but they were fat. Her areolae were super dark, and covered nearly the entire front of each tit. I started to gently play with them.
"Mmmmm I love nipple play Jack. Keep going."
I kept at this for a while and eventually she started playing with herself. I could tell she was getting wet by the sounds her hand was making in her vag.
"Okay, it's time".
With that she put me on my back and straddled my face. She lowered her dripping cunt on to my face and said, "Get to licking."
I started with her lips using my thumb to play with her larger than average sized clit. She then started grinding onto my face. Her breath increased and with a few moments she screamed, and her pussy creamed all over my face. She didn't relent... she rode my face to another orgasm, each one stronger than the last. When she finished her second orgasm that way, she dismounted my face and slid down my body.
"Enough of this! I need this hog you call a dick in me now!"
She grabbed a hold of my hard cock and impaled herself on it all at once. She started riding me like there was no tomorrow. She was so would up that she kept on cumming, coating me in her love juice.
"Fuck! Fuck! Fuck! Fuck yeah... yeah yeah OH MY FUCKING GOD"
This orgasm was so powerful that I could feel her pussy clenching and throbbing on my dick.
"Fuck I'm gonna cum!" I said.
"DON'T YOU FUCKING DARE! HOLD THAT SHIT OFF UNTIL MY NEXT CUM!"
She stopped riding me while I composed myself and started slowly, rubbing her clit the entire time. As she brought herself closer to orgasm, she started riding me harder.
"FUCK! FUCK FUCK FUCKING FUCK OH MY GOD THIS ONE IS GOING TO BE BIG! CUM WITH ME JACK CUUUUUUMMMMMM!!!!"
With that she shrieked again, pushed down on my shoulders for leverage and drove herself onto my cock. I felt her pussy cream and then pulse again and that send me over the edge. I shot stream after stream of hot jizz into her pussy. After that I stayed inside her as I softened. When I pulled out, a flood of my cum literally fell out of her. She slid up to my chest and gave her clit one last rub, gave herself a small orgasm, and squirted a combination of my cum, and hers onto my chest. She then kissed her way down my body, licked up the mess, and proceeded to clean my now soft cock with her mouth.
"Fuck that was great."
"You're telling me," I said.
"Okay Jack, it's nearly midnight. I'm sure I could get you hard again, but we both have to work tomorrow. However, I'm not quite through with you yet. You've had my mouth, my tits, and my pussy. Before the week is over, you'll get my ass too. You're welcome to stay the night, but no funny business, unless I initiate. And if you DO wake up with a morning hard on, if I don't take care of it you may NOT jerk off. Is that clear?"
"If you can't live with those rules you can leave. We will only get together again if we run into one another."
I decided that I would stay. Of course, I woke up hard, I rolled over to see her playing with her pussy again.
"I thought you'd never wake up. Get the fuck down here and finish me off."
I didn't need to be told twice. Went to work on her clit, and within minutes she was moaning, writhing, gushing and screaming out her orgasm. She looked with pity at my hard cock.
"Okay, but you'd better not hold this one back. I have to get to work. With that she lubed up my cock with her mouth, fingered my ass and took me balls deep again. She massaged my cock in her throat and in record time I was shooting another big load into her throat.
"Okay. Get going. Be back here in the room waiting for me at 7pm."
The day seemed to last forever. My mind was a million miles away. I grabbed a sandwich on my way back to the hotel, ate it in my room. At precisely 7PM, I let myself into her room. It was empty. I sat and waited patiently on her sofa. She walked in at 7:15 and said nothing.
She kneeled down in front of me, fished out my already hard cock and said "Shhh... not a word. Remember the rules or you get nothing else from me."
She took me into her mouth and began bobbing up and down on my hard cock. After 4 nuts last night there was no way I was going to come that quickly, but her skills were so amazing it took about a minute before I was flooding her mouth with my goo.
"Bedroom, now", was all she said.
We went into the bedroom and got undressed. She got on the bed, spread her legs, and guided me into her sopping wet snatch.
"First fuck me... I need a quick orgasm before I give you my ass. And no cumming!".
I mounted her and started giving her the pounding she wanted. She started rubbing her clit and after a few more minutes, she was once again gushing, screaming and squeezing my cock with her pussy muscles. Then she reached into a drawer. Pulled out a bottle of lube and a bullet vibe.
"Here.... Get my ass nice and lubed. That cock is about the biggest I've ever put in my ass before".
I did as requested as she bent over and offered her ass to me. She went to work on her clit with the vibrator as I stuck first 1 finger then a second into her ass. She started moaning softly, and just for good measure, I lubed up my hard cock.
I said "Okay.... Here it comes," as I slowly put the head of my cock in her.
"Wait,, let me take control. Just hold on to my hips."
I did as she asked as she slowly began fucking herself on my dick. Slowly at first. Then she got a rhythm going but still only had half of me in. She went to work with the vibe on her clit. She began fucking me harder, then said "Pull my fat nipples. Twist them. Make me scream!"
I did as she asked, then I started fucking her back. Eventually, I grabbed her huge hips and started pulling her into me. She was still using the vibe. "Holy fuck goddamn, your tearing me up! Don't stop! I'm going to cum! Pound my ass! And don't you dare cum!!" I lit into her and pounded her ass for all I was worth. "FUCK FUCK FUCK FUCK FUCK OH MYGOD HERE IT COMES! Ahhhhhhhhh!!!!!" With that her pussy squirted and her ass started convulsing on my cock. She pulled off of me and turned over, opening her legs. "Stick it in my pussy and fucking fill me up!" I shoved me cock into her and in no time, I unloaded my spunk into her. We rolled over, collapsed, and fell asleep.
The next day was my last day in DC. I awoke to a slow sensual blowjob. I unloaded into her mouth and then licked her to a slow, sensual orgasm. We showered together, then said our goodbyes. I did ask for her number and last name. She wouldn't budge. Said I was fun, but I was a travel perk, no more no less. I ran into her about 2 months later. We fucked our brains out for 2 days. I snooped around her room and discovered her last name, but it was no use.
Comments of course are welcome.