Blue's Magic -- Monica

A. Friendly Stranger

Many thanks to member hotti for valuable assistance making this story readable

I spend most of the winter in Florida, and in early February I was making a weekend trip, mixing business and pleasure. The trip was south down the coast of Florida and I would be traveling alone. About a week before I left home, I posted my reliable personal ad to Craigslist 'casual encounters' in the area I was going to. The ad mentions that I like BBW's and also my generosity toward my lovers.

I was not exactly overwhelmed with responses, getting exactly two emails in the first 24 hours. One was from a Craigslist 'pro' (a woman who trolls for customers), but the other was from a real woman.

"Hi,

I am a sexy BBW....who likes to play......I could be available that evening. I am in xxxxx FL. I love to please and pleasure......I love to give oral.......and I love kinky sex....

Hope to hear from you"

Sexy Gal

She sounded like another pro, so I said I was only interested in a BBW, after which she sent me a picture, and the following:

"Hi Friendly Stranger,

I am a size 22....5'8"...42 DD.......I'll send a pic......"

Sexy Gal

Her picture showed she was a nice looking BBW; we exchanged several emails to establish our 'fides with each other, and told her my real name - then we got to the nitty- gritty and I received the following email:

Hi Al,

My internet name is sexy gal.....lol...my real name is Monica. I am married as well, disease free, and very clean with a shaved pussy.

I work part time nights and weekends...I will be working Friday night until about 8:30 or 9:00 pm...and could be available for a "hot sex session" afterwards. I more than likely will be working Saturday as well (I always do).....and will be off around the same time...(sometimes earlier)...and could be available afterwards again for another "hot sex session".

I love my pussy eaten and played with.....however you wish.....tongue, fingers, hands....I will come to you very clean.

I really enjoy sucking and playing with a cock.....and would enjoy the challenge of having you cum twice....or more......

I really enjoys toys...unfortunately I don't have any.....maybe it's time I get some....lol

I have never been "paid to play" before. If I come to you, I do so with the intent of pleasing and pleasuring you...anyway you wish..with no monetary expectations.

However, I am in a very stressful financial situation...so .....I will let you decide how to handle that.

I look forward to hearing from you,

Monica

I honestly couldn't believe my good fortune. I emailed her the amount of money I had budgeted for sex on the trip. I mentioned again that I loved to kiss and make out and eat pussy. I got this email:

"Hi Al,

Yes, what you have budgeted is generous enough, thank you. Hopefully, if it goes as well as I anticipate, and our schedules allow, we can get together Saturday night as well. I do love to kiss and make out. Unfortunately I do smoke, but I am a polite smoker....if there is such a thing...lol. I will of course use mouth wash, mints, etc. A smoking room isn't necessary, I wouldn't smoke inside anyway If I were to smoke I would step outside.

I do enjoy a drink or two....but it's not essential for a good time.

I'm sorry, but I don't have many pictures of myself on my pc....I do enjoy communicating via email.....as often as you like. I also enjoy phone conversations....when time allows.

My cell phone # is XXXXXXXXXXXXXX...you may call anytime, whether or not I can talk will depend on who's around at the moment....but I can always step outside for at least a minute...if not more. After 10 pm is almost always safe.

Look forward to hearing from you,

Monica

I sent her a graphic email of the things I wanted to do (eat pussy mostly!) and she replied:

mmmm...Al

My nipples are hard....and I'm wet thinking about our encounter. So far it sounds like we will pleasure each other very well. My drink of choice is rum and tonic w/ lime. Please, I prefer a dark rum...Bacardi or Myers.

I like what you described...very well. I like to start out soft and gentle....but then ...I also like it hard and rough. I am new to experiencing a few things, bondage and dominance. I like it when the man takes command of the situation. I am willing to please you any way you wish....whether or not I am experienced in what you ask may be a different matter....so be patient with me...and know my intent is to serve and please you well.

I am also discovering that fine line between pleasure and pain....but that may be for another time.

I love anal sex.....hard....mmmm.....I've had my ass licked before ...it really didn't do much for me.....but if you enjoy it I am willing to lick yours...I have only once before.

I really enjoy sucking cock...and I do it very well. I want to taste you....mmmmmm

I look forward to meeting you,

Monica

Some of the things she had mentioned I don't know anything about (rough sex, bondage & dominance), but she said she would please me, so I thought things would be okay. We exchanged several more sexy emails over the next several days and finally Friday rolled around. The town where she lived was about 250 miles from where I was staying, so I left about midmorning.

There was no cell phone coverage in the remote village where I was staying and when I got in range of a cell tower I found I had a message from her – she had cell phone problems and was using her husband's phone and gave me the new number. Her voice sounded very sexy to me and I played it a couple of times just to be "closer" to her. I was also a little nervous about her being married and also about the "pay" aspect of this date - I hoped I wouldn't meet her husband or a deputy.

We had agreed on a hotel and I had made a reservation - when I checked in, I called her cell and left a message with my (our?) room number. The room was in a mid-price chain located near the Interstate. From the window I could see the entrance road. I got a bucket of ice, showered, and then paced the room and watched the road. I was as nervous as I have been anytime since I was sixteen.

She didn't arrive until about 9:45, and I was a real bundle of nerves by then. I had brought some dark rum, and I left the agreed amount of cash right by the bottle; when she arrived I had her make herself a drink so she would see the money - I feel awkward handing a woman cash.

Almost immediately we started kissing and running our hands over each other. She was very hot and loved kissing. After a few minutes of play, she said, "We are going to get along good."

I was relaxing and really starting to enjoy myself. I was very gentle, kissing and feeling her luscious big breasts, and feeling her legs under her skirt; she wore a skirt because I had asked her. I discovered she had worn no panties. I gently began to fondle her pussy, barely parting it with my fingers, all the while kissing her mouth and and kissing and licking the nipples of her big breasts. Then I gently eased in a finger and felt her wetness. Her pussy was so smooth and felt so good.

With my hand cupping her pussy, I squeezed and my middle finger slid into the moist slit and I began to very gently stroke her clitoris. I played with her like this for a while, alternately squeezing harder and softer and letting my finger slide up and down between her luscious full lips. My fingertip dipped sometimes into her sopping hole. She really liked it and was moaning between our kisses.

I knelt on the bed between her legs and I began to lick her pussy, just running my tongue around the outside, and sometimes dipping my fingers into the wetness so I could lick it off and taste the sweetness of her. She lifted her big legs in the air, spread wide, and held them open to allow me total access. I went to work on her pussy, kissing and licking it and working my tongue into it. I then focused serious attention on the clit –licking, and gently sucking her sweet button with my tongue and lips. I spread her open with my hands.

She was moaning and writhing. Her slick juice was all over my face, my nose was pressed right into her cleft and her taste and woman's smell were almost overpoweringly delicious. My cock was erect and throbbing.

She was on her back, and hoarsely whispered, "Turn around," and with tugs and gentle pushes positioned me straddling her head with my hard-as-a-rock cock in her mouth and my head between her legs - kissing and licking her yummy pussy. We worked on each other for a while like this and then we rolled over, with her straddling my head; my wriggling tongue deep inside her while she vigorously sucked me.

I pushed a pillow behind my head and licked and tongued this magnificent woman from the mons to the anus. As I licked the length of her, my nose went from the dripping hole to the rosebud of her butthole. The view in the dim lights from below of her quivering ass cheeks was absolutely exciting. I embraced her big butt and pulled her to me, squeezing and feeling of her soft cheeks with my hands.

I was holding my climax back and waiting for her - I didn't really have to wait too long. She stopped sucking me and started rhythmically gasping while she squeezed my head between her legs. I redoubled my efforts and was rewarded as she very obviously started to cum. She gasped and moaned and her pussy contracted - she even squirted a little sweet pussy honey; I savored it. We lay end to end and rested a few minutes; she was breathing pretty hard and was flushed.

"Now I am going to make you cum," she said and straddled me and started riding cowgirl style, reaching back and playing with my balls. I was already pretty excited - so excited I had her get off and lay down on her back; I had her legs in the crook of my arms, bent back and knees pushing on her big boobs. Her pussy was so exciting.

She said, "I want you to cum inside me," and after all this wild sex, once I let myself go I came very quickly, pushing as deeply inside her as I could and gushing hugely.

We were real friendly by then, and we started talking about ourselves and our sexual adventures. She was forty two, had three kids, a Honduran husband - she was a white woman - and had only recently begun to explore her sexuality through the personals. She had not been sexually active for years - only occasionally with her husband. She just hadn't been interested. She even gave me the date she started playing on CL – in the previous December.

She had really undergone a sexual awakening - I don't know if the horniness preceded her curiosity that led to the personal ad browsing, or followed it. She hadn't been a nun before, but her youngest had only recently started school and she apparently wasn't as tired as she had been for years. She had decided to tell her husband that she wanted their marriage 'opened up', but had not done so yet.

I had gotten a smoking room so she could smoke. She sat in the easy chair and I pulled the desk chair over in front of her chair and slouched down in it. She had the recliner partway inclined with the footrest up and we both had our legs resting on it, touching. We were relaxed, both still naked and she was having a rum and tonic and a smoke while we chatted. She had had several good experiences using personal ads. This was her first time for money.

"The idea of fucking a stranger for money got me excited, to be bought like a slave," she explained.

Another ad had led to her meeting with two guys - she had met them at a warehouse in an industrial park "They were nice guys, they fucked me up one side and down the other." She also had experiences with a woman, who was now a sometimes lover - Monica said she's a nice woman but that she, herself, liked men.

She had said in one of her emails that she had started to 'explore the fine line between pain and pleasure', and she talked about this; she had started meeting someone who mixed sex and pain and she really enjoyed it. This seemed to be the sexual direction that she was headed. This girl was no scaredy cat! She had other adventures besides these. Everyone she had met was a nice person. I told her this could be dangerous, and she said, "I trust my instincts."

After we had talked awhile, my cell phone started ringing – it was my wife. We usually talk on the phone late in the evening when we are apart and tonight wasn't an exception. I had told Monica to expect this, and I was glad we weren't having hot sex when the phone rang. At first I went into the bathroom and talked, but after a while I went back into the room and sat in the easy chair.

I was chatting away, and Monica got a wicked smile on her face and came over, knelt down in front of me and started licking and sucking my cock. I immediately started to respond by getting hard. She was working away, and I was trying to keep from gasping and moaning while I talked to my wife. Finally I told my wife I needed to go to sleep because I had a hard day tomorrow and hung up. Monica and I jumped into bed, giggling like kids.

We started kissing and licking each other again and soon she was moaning. We played around with each other for awhile and then I knelt between her legs. I was playing with her pussy, using two fingers inside her slick pussy- massaging her G spot. I used two fingers (palm up) and reaching inside as far as I could, I then curled my fingers in a 'come here' type gesture repeatedly.

Many women love this and she certainly did, too. At her direction, I started doing it fast and hard, while I was kissing and sucking her clitoris. She came pretty quickly and again I tasted a little squirt of her. She was breathing pretty hard and I still had my fingers inside her. Her pussy was extremely wet and I started working another finger inside her.

She said, "Yes!" so I worked more fingers into her. I squirted lube on my hand, squeezed all my fingers together and worked them inside her. I wiggled my fingers and she gasped and I then had all my hand inside her. I balled my hand and worked it in to the wrist. I slowly pumped my fist in her, pushing gently in and then pulling into the tightness of her pubic muscle. Each time I pulled she gave a low moan. I started to slowly rotate my fist as I fucked her with it.

I put my free hand on her pussy, the heel of my hand on her pubic bone and my fingers splayed over her ample belly. Through my fingers I could feel my fist moving inside her. She was gasping and moaning, her head was thrown back and she was thrusting her pelvis toward me. I leaned down and with my tongue pushing hard against her clit I started shaking my whole head from side to side while I rotated my fist from side to side. It wasn't long before she shouted "YES!" and had a great shuddering climax. I unclenched my fist and very slowly eased my hand out of her, as my knuckles slipped passed the final tightness she shivered and moaned in pleasure.

She then got on all fours on the bed, stuck her big butt up in the air and said, "Fuck me in the ass."

I was only too happy to do just that! I put a little lube on my cock and started easing into her. Her asshole was very tight. She gasped when the purple head slid past her tight sphincter. I was gentle at first, and slowly sunk myself in her as far as I could. I quickly got very excited and so started to fuck her pretty vigorously, and she moaned and gasped. She pushed her backside toward me the whole time as I took my pleasure with her. It didn't take long before I was squirting my satisfaction inside her. I pulled out, collapsed on the bed and we lay there panting, grinning at each other and kissing.

It was pretty late by then, and she started to worry about getting home. We were both drained and satiated. I gave her another fifty bucks, and we exchanged a few more kisses and then she left.

I emailed her that night, thanking her and asking about meeting the next night and received the following reply the next morning:

I had a very nice time also....you are very good....mmmm.....thank you so much for your generosity....I really appreciate it.

I will have my phone....you've got my number.....I'll be at work....so leave me a message if you like...and I'll call you when I get off. If not, then call me the next time you come to town.... Monica

My business took me about 80 miles up the coast on Saturday and was exhausting, so I never called her. She was a sweet woman and I was glad to help her out. I do not mind paying a non-pro for sharing her precious intimacy with me, and look forward to doing it again.

She told me more than once that the money wasn't a factor. I did not treat her rough or in a painful manner - she liked the fisting and I was gentle doing it. This woman was not young and didn't fit the cultural definition of beautiful, but I had as good a time with her as any other woman in my life. She genuinely appreciated being appreciated and did her very best to return the favor.