This is a partially true story - the very first part happened up to meeting as her study schedule didn't afford us the time - however, we shared some exciting e-mails and fantasies that night. I promised to tell the story as I thought it would happen had we actually been able to meet...
I was traveling back to what I used to call home for a reunion of sorts with the guys I played sports with in my 20's and 30's. Here I was on a cool, rainy Sunday night before returning home, tired but still with lots of vim and vigor - so as an average middle ages white man, I was horny as hell.
I wandered over to the computer after working out in the hotel gym in t-shirt and loose fitting shorts. I thought I would place an ad on Craigslist to see if I might meet up with someone that night - or possibly to my favorite web-site a bit later for some good material to get myself off - assuming I would receive no positive responses. For an older man I was still in fairly good shape - late 40's with toned legs but certainly not the toned athlete of years past. I placed my ad for providing a free massage for a woman hoping someone might be interested in receiving some TLC from my learned hands and perhaps allow me to please her orally. If I was truly lucky she'd let me massage myself to orgasm in front of her (I have a fantasy for that humiliation which I rarely get the opportunity to participate in).
After a couple hours off and on browsing posted ads myself I found one that seemed a bit interesting to respond to - a woman looking for someone to play with her nipples and to please her - not looking to reciprocate. Just a simple ad with no age, etc, just mentioning playing with her nipples and not being able to host. I wrote a simple response back describing myself with a g-rated picture, offering my "services" to massage her back, body and certainly her nipples. I explained that I had placed an ad earlier for a free massage from PG to a sensual X rated massage including her nipples and pussy until she was fully relaxed and pleased. I offered oral as well, if she wanted and sent a copy of my ad. This included noting that I would like to please myself in front of a lady as well.
Surprisingly, since there are dozens or hundreds of guys who probably answer ads like this, I received a nice reply back. She told me she was a nice, curvy woman who enjoys being pleased but rarely has had anyone take the time to spend time on her needs. She also mentioned that she'd love to watch a guy do himself. Although she hadn't seen it before it was one of her things she's thought about in the past, especially if the guy would cum on her breasts. She also included a picture of her, topless. She had some wonderfully large and firm looking breasts with small, pert nipples. I was hard immediately and quickly fumbled with the mouse and keyboard to supply a response.
I wrote back that I'd really enjoy giving her a show and I'd love to cum on her breasts. I'd never had the chance to do that before, although one time I did cum on a girlfriends hairy bush after pulling out - it looked so good that I even wanted to taste it (since I love giving oral sex more than anything). I mentioned it was part of my "bi-sexual" / fantasy side - along with taking a strap-on, etc.
Although about 30 minutes - her reply seemed like an eternity. Not only did that turn her on even more she wanted to know if I'd really cum on her breasts, rub it all over her breasts and still lick it up. She even noted she had a toy or two she'd like to share with a guy - assuming she found someone adventurous enough to play with in this manner. Before I knew it she asked where I was and could we meet tonight still (it was getting very late).
Before I knew it she told me she was on my way and would meet me in the hotel lobby in an hour. I rapidly took another shower as I'd been rubbing myself for well over an hour and knew it could probably use it.
I knew her when she entered the lobby, although cold and damp out and she was wearing an overcoat her look was between apprehension and desire. She was much taller than I thought - about 5 inches shorter than my 5'11" frame, black lightly wavy hair damp from the shower and like me, thinking we are average but that's more our feeling about ourselves than how we are actually perceived. She was truly a vision and for a moment or two I didn't think of the slightly kinky discussion we had earlier. I stood up and her eyes found mine and she smiled nervously. We made our way to the room I had with idle chatter about her drive, the weather and why I was in town.
After getting to my room she pulled back her coat and she had a tight fitting top on that fit snugly against her large breasts. I didn't normally go for ladies with larger breasts but like some I've seen these looked great - well proportioned to her body with nice cleavage. She also had on a somewhat loose pair of sweat pants which left everything to the imagination - but still gave the image of a wonderfully sexy lady.
I asked her if I could rub her shoulders as I moved towards her. She cooed a yes under her breath. I reached up and could feel her tense shoulders under my fingers. I started kneading both shoulder blades from the nape of her neck down to her upper arms and back again. On the third trip down from her neck she asked - no she told me - that she came here for a reason and that she was dripping wet thinking about me massaging her breasts. I reached up and around as I stepped forward and firmly but with care held both of them. While heavy they were certainly firm with a definite bounce to them. I wondered how well they'd hang up with my hands and her bra holding them up - would they be as firm and supple as they looked in the picture.
It was as if she read my mind as she reached down and yanked her top off, struggling to get it off her body. I reached back and unsnapped her bra and was about to let it fall when she told me to touch her nipples now. As her bra hung from her shoulders I reached up under the cups and felt her very warm breasts. She backed up into me, feeling my body against hers and for the first time I felt the hard-on I developed straining against the fabric of my shorts. She leaned her head back and I passionately but tenderly kissed and nibbled her neck and ears - first her left side then the right. Meanwhile I firmly cupped her left breast while I lightly played with her right breast and nipple. Moans were starting to escape her lips - low at first but then louder with lust.
She turned around quickly and gave me the most passionate and hard kiss I had ever had. Firm and lustful, but with and without tongue, like neither of us had ever experienced a kiss before or if we broke it off it would be like without having oxygen. After a few minutes she broke off the kiss but only to push my face between her breasts - telling me to start licking. I start on the right breast, holding it while I kiss and lick it - nipple here and there. I alternate my speed and technique and always have one hand on each breast gently rubbing and tugging the one I don't have my lips on at that time.
After what seems like 15-20 minutes of this she pulls away from me. She rushes over to the bed, pulls her sweats down and flips them to the side giving me a great view of her apple bottom. She turns around and lays back on the bed and orders me to lick her pussy - NOW! I quickly kneel in front of her and don't hesitate - diving straight between her legs, barely noticing her furry mound. She is terribly wet and I start licking up all her juices. Instead of letting me clean her up she has other ideas and grabs my head and pushing my nose into her lips, ordering me to get her off right now. I stretch my head up a bit and find her waiting clit and attack it with my warm tongue and lips. She doesn't let go of my head, keeping me right there to use me as her personal sexual device. Barely able to breathe I just start getting a good rhythm going when she pulls me even deeper into her wetness and clamps her legs around my head and starts humping my face. Seconds later I'm flooded by sounds of her orgasm and juices as she rode my face. I kept licking as best as I could and when the sensations started to subside I slowly stopped licking and gingerly kissed the insides of her thighs as she released my head.
I crawled up on the bed next to her and gently massaged her breasts and stomach, occasionally caressing her head. I was still fully dressed except for my shoes which I happened to kick off while getting her off.
When she recovered sufficiently with her breathing returning to normal she looked over at me and told me to stand-up, strip and go sit in that chair and start masturbating as I said I was going to do. I stood up and quickly pulled off all my clothing. My shorts were a bit damp from all the pre-cum I had leaked earlier - but I was mostly soft at this time. As I sat back in the chair my average size cock had already sprung to attention to the gentle tugs I had managed so far. I looked over at her and started seriously tugging at my meat, often times stopping to grab my balls with the same hand or rub balls and cock against my own body. I had my legs slightly spread and she asked me to make sure I don't cum on myself. I should just sit there until I was ready to cum and tell her when I was close. With that, she found her purse and pulled out a vibrator of medium length, got back on the bed and shoved it deep inside her with a big oooohhhh associated with that move.
Although I hadn't been hard the whole time I was servicing her, the anticipation of meeting her and fondling myself before then and her nakedness produced some quick results. I told her I was close and she asked me if I was clean.... I didn't understand but noted a took a shower when she was on the way over. She told me to climb up on the bed and lower my balls and cock by her face pointing at her breasts as she wanted to see me cum on them. I didn't have to be told twice. I lept up on the bed, tossed a leg over her head and started stroking. I could see her breast heaving with her breath and noticed she had removed her hands from the vibrator but left it deep inside her - muffling the sound it was making. Within seconds I was ready to cum again and before I could say anything I started cumming about as much as I've ever cum. I definitely made some hard animal sounds when I came with most of the cum on her breast and bit more on her stomach and my hand.
As I pulled away from her I started to walk away and look for a towel for my hand. Sensing that is what I was doing she ordered me to stop. She told me that I was going to massage my cum on her breasts as we talked about in our shared e-mails. But since I missed and had cum elsewhere I was to clean off all the cum I missed with first with my mouth. I was no stranger to my own emissions but never this quantity and didn't think twice as I looked at her and licked my fingers with cum on them. She smiled and inspected my work then pointed to her stomach. I inched down there smelling her moist pussy as I went by. I traced the cum up and got most of it in the first try then licked up the rest. I sat down beside her and started massaging the rest of my seed on her breasts at the same time, at first in circular motions then in a more kneading fashion.
Satisfied with my efforts she told me to start licking her breasts and use my hand to fuck her with her vibrator - make sure it got nice and wet. I must have licked her breasts for 30 minutes gently while slowly toying with her pussy with the vibrator. She was moaning slightly and wiggling a lot. Without much warning she first slowed down to a light rock on the vibrator then started thrashing hard while I held it inside her. She reached down and grabbed at her own clit, rubbing it hard and humping away. She came very hard. I turned off the vibrator but left it in for a few more minutes as the small aftershocks of her orgasm tingled her.
A few minutes later she snapped out of her bliss and thanked me - told me I had done well and done what I said I would - now it was be her turn to help me. She told me to crawl up on the bed on my hands and knees face down which I quickly did. She rolled off the bed and pulled my feet towards the foot of the bed to square me up and told me to be still. She flicked on the vibrator that she pulled out of her and started running it along my cock and balls up and down then further up the crack of my ass. She didn't take long before she pointed the business end of the vibrator at my hole and pushed in slightly - enough for me to gasp. She moved it in and out a few times then started a slow push deeper until it penetrated the ring and I could feel my ass gripping the device.
She told me to hold it there and not to let it go - if I wanted more. I held it as best as I could as she let go. Right before I was sure it was a goner she grabbed it and pulled it out slightly. I then felt a sharp, cool sensation dripping down my ass - some sort of lotion. With one hand slowly dripping lotion down the other one was gently moving in and out of me, slowly turning this way and that - like she was trying to spread the lubricant all around. I could feel lotion dripping from my balls and some from my cock when the coolness stopped and I noticed she was a bit deeper than before. I heard the snap of a lid to close the lotion then felt her change hands on the vibrator. The next step brought me back from nice enjoyment to reality - she had gripped the entire end of the vibrator with her hand and shoved the remainder all the way in my ass. I gasped for air before I let out a "FUCK" into the sheets. It didn't hurt as much as it was pleasure I hadn't felt ever before.
I had a few small dildos before but nothing felt like this - it easily penetrated me and hit all the right spots. After she asked if I was all right she started moving the tool in an out of me with fairly good speed, getting faster and faster until she started banging her fist at the end on my ass much like a guy would pound his pelvis into a woman he was fucking hard. I was besides myself - all sorts of words and emotions were filling me. After a few minutes she switched hands and with the hand that was free now, grabbed my balls and started tugging, then slapping my cock until I reached a full erection.
She ordered me to flip over on my back with the tool firmly inside me. She pushed it in what I thought was most of the way and replaced the pounding of my ass with the toy with her pounding my meat. She beat it as hard as she could and it felt great. This went on awhile until she started to tire. She then told me - "You have 5 minutes to cum. Then I'm leaving without a word." Quickly I moved her hand away and wiped my cock of the lotion that was lessening the friction and started to pound my own dick with a fury I couldn't remember. It didn't take long - exactly how long I don't know - but I started cumming again all over myself with my legs in the air like I was getting fucked like a woman.
As soon as I stopped cumming and put my legs down she yanked out the vibrator leaving me wanton for more. She told me to relax and stay still. She quickly washed the device and put it and the lotion away and dressed. As she walked towards the door she said thank you - when you come this way again please write - perhaps I'll have a strap-on then and really fuck you good. I put my head back and fell asleep with my cum still on my hand and chest.