Long time lurker, first time contributor.
In the late 90s I was in my early 30s, newly divorced, living in a small town with an almost non existent population of single women. My ex was awarded our friends in the divorce and I felt bored and trapped and had little to do beyond driving my kids everywhere they needed to go on the days they were with me and when I wasn't working.
I was a temporary IT guy and spent a lot of time in front of a screen both at work and home. In my need to connect with anyone I discovered chatrooms, messenger, ICQ, online backgammon and long list of other places where lonely people went online. I lurked in chatrooms and did things that you do when you are anonymous, bored, discovering for the first time what other people thought about sexually and able to type 60 wpm with your left hand. At night I could be found typing away trying to keep track of multiple messenger conversations, a backgammon game or two and illegally downloading pictures, videos and stories of an adult nature. I trolled for (a fishing reference not the creature under the bridge) what I certainly hoped were women in chatrooms with titles that told you what the kink du jour was.
Every so often I would find someone to have "cyber-sex" with and would spend a half hour or so trying to quickly type a scenario that was both witty and dirty and interesting enough to elicit more than a "mmmm…." in reply. Sometimes I would click with someone and we might go 2 or 3 days finding each other on line and message back and forth. Sometimes this would even lead to phone sex which was awkward because you had to give or get a number, go off line and make or wait for a call.
Now remember that this was before texting and portable access to the internet. Hardly anyone under 40 remembers this but once upon a time you connected to the internet with a modem and a home phone line and it was called "dial-up". 56kbps was an almost unimaginable speed and most of the time you just felt lucky if you could download a short video clip in under an hour.
Eventually I found Robin. She had a lot of Daddy issues, gave as good as she got by phone and keyboard and had a lot of time on her hands working in a college library in front of a computer. And she was able to make long phone calls free of charge . After the first phone call I was hooked. The southern accent, the role plays she could come up with, listening to her masturbate as I told her what a bad or good girl she was and how I was going to spank her with my cock down her throat. She would go to an empty office of the library and lie on the floor behind a desk and listen to my voice as she masturbated. I heard slapping and asked what she was doing. She told me that she sometimes slapped her pussy when she masturbated as she was doing now and how good it felt and how she imagined my hand doing that too her. She was always a dirty girl and expanded my ideas about what was arousing and that a bit of pain was not such a bad thing to her.
Up until this time I have to admit that my horizons had been some what limited. I had married while still in college and after the first child sex had become infrequent and somewhat inhibited which I guess happens when you run the risk of someone small walking into your room and asking if you and mommy are wrestling.
Phone sex with Robin led to talking about actually meeting and shortly I convinced her to fly to New England to meet me. Now I should mention that up until this time I only had a vague idea of what Robin looked like. Digital cameras were rare at the time and the alternative was to find a scanner and run a physical photo through it. I had been sent pictures by a few women at this point but they were kind of a mixed bag of picture quality. Robin’s was a little less detailed than most but what was clear was that she had great breasts, was not fat and from her outline was very appealing. But it had never been about what she looked like it was what she sounded like and what she thought and what she said she wanted me to do to her over the phone.
I sent her a ticket and it felt like forever waiting for the day that she would arrive. When I went to pick her up at the airport I was a little worried that I would not recognize her and made very sure that she knew exactly where to wait for me at the airport. I arrived a little late and looked around the luggage pick up area for her, There were very few people there so it was relatively easy to pick her out as the only woman in her 20s sitting there. I have to admit that I was a little surprised and felt a little guilty that my initial reaction was that she was homely. What was the real shock was how short she was. I’m only 5’8” but the top of her head barely reached my shoulders. I guess she was just about 5’ tall if not a little less. I quickly regrouped and hopefully offered her a warm welcome as I pulled her toward me and hugged her hard as whispered in her ear how happy I was that she made it and how much I wanted to see her naked.
Our conversation was pretty easy and I made her laugh several times as we walked to my car. I threw her bags in the back got her into her seat. It sounds a little weird to say it now but we had actually talked about this happening and part of our play was that I would buckle her into her seat belt to make sure she was safely locked in and protected . There had been a little age play and daddy daughter discussion as part of it and it had definitely been an unexpected turn on when she spoke in that innocent little southern girl voice as I put the belt around her and snapped clicked the buckle. Her voice was soft and breathy as she spoke into my ear and I remember being very aroused very quickly without ever being touched.
I headed out of Boston as fast as I could and headed north. Our talk quickly returned to our role play and I put my hand on her thigh as I told her what a dirty girl she was and how I couldn’t wait to get her to a hotel. She put her seat back and brought her legs up as she pulled her skirt up her legs. At first I played with her running my hand across her lap to tease her before placing my hand directly on her mound to play with her pussy through the cloth of her white cotton panties. There was some traffic and I found it nearly impossible to steer, shift, pay attention to the road and pay attention to her pussy. I told her that I wanted to watch her play with herself as she told me how it felt and what she wanted her daddy to do.
As the traffic cleared up a bit and I could speed up she asked if she could lie her head down on my lap as I drove. It was a little difficult to negotiate with the emergency brake and the shift but she managed to arrange herself across the console with her head in my lap. It took her no time to bring her hand up so she could touch my cock through my pants. I made small talk about how she was a good girl and how good she was making me feel. She took this encouragement to bring my zipper down and to pull the head of my cock through my boxers. She stroked it for a second and quickly put her mouth over it. As I said before she was very short and small and I felt huge in her small hands and her little mouth. She was game and took as much as she could but it was hard for her to get her mouth all the way around me. As she had her head in my lap a commuter van from a factory or something pulled up next to us and because they were higher up they could see right down into the car with her head bobbing up and own on my lap. I noticed them immediately and looked over to see them pointing and laughing and giving me the thumbs up. I told her to look up and see what was going on next to us. She was shy but didn’t take her mouth off of me as she looked up at the people in the van.
It felt like it took forever but I finally found a motel and got a room. I got us to our room as fast as I could and brought our bags in. She sat at the edge of bed and just looked at me expectantly. I told her stand up and I sat where she had been on the bed. I told her to start taking off her clothes because I wanted to see all of her as she turned around in front of me. She complied while keeping up the shy girl act. She took off her shirt which revealed her plain white bra and pulled her skirt down to show me her plain white panties. I gestured that she should continue and she turned from me as she undid her bra and pulled her panties down. I pulled her back to me as she kept facing away from me and ran my hands up and down her sides and cupped and squeezed her breasts. The other surprise I got at this point were how bright and colorful her tattoos were. She had told me about them but she had never completely described them and I had never asked too many questions. There was a dragon running downward across her stomach and across her pussy. There was another across one of her breasts with the other one bare. It was a first for me, exotic and arousing. It felt a little creepy but I touched her all over while I made little noises about how much her daddy loved her and what a good girl she was being. I stood up and made her undress me, undoing every button of my shirt and kneeling in front of me while she undid my belt, tugged my zipper and pulled down my pants.
I hadn’t believed her when she told me on the phone that what she wanted was for me to tell her everything I wanted her to do for me. But as I began directing her I started believing. I could tell that she was getting off with each direction and the more firm I was with her the more she looked like she was melting. Given her size I found that I could pick her up with no trouble and so I threw her on the bed and buried my face between her legs. She was the first woman I had been with who was completely shaved and I found it fascinating to explore her in the light and slowly explore every inch and every fold of her. She was unbelievably responsive and forced her hips up against my face. I pushed her down into the bed and held her down as I explored her with my mouth as her legs hung over the bed. As small as she was I could move her easily across the bed as I licked her and rubbed her and penetrated her with my fingers as I rubbed myself against her.
Then she caught me off guard when she asked me to spank her while she sucked my cock. She had talked about it in our play over the phone and on messenger but it had never completely connected with me that it was something that she fantasized about and wanted me to do to her. She lay across the bed with her head in my lap which put her ass right where I could spank it. I started off somewhat tentatively because this was a first for me and I wasn’t sure what “spanked hard” meant to her. What I found out was that it meant hard enough that it hurt my hand and made her ass an angry red that I was worried would leave bruises. That turned out to be what she was really looking for. It made me uncomfortable at first but the more I did it the harder she sucked me and the wetter she felt when I fingered her between swats.
As much as I was learning to enjoy spanking I was really looking forward to looking at her twat tattoos while I had my cock in her. I moved her around the bed again and put her face down into the mattress as I lifted her ass up. She wiggled in front of me and started to make little whimpering noises talking in her little southern girl voice again alternating between telling me how much she wanted me to enter her while she worried that I was going to hurt her with my cock. But she kept moving her ass back to me and it was tough to rub the head of my cock around her pussy without entering her. The wait was worth it. When I started pushing myself into her I found I had to work my way in slowly a little at a time so she could take me in. The short strokes made her wetter and she pushed herself back even harder. I could tell that I was hurting her a little but it didn’t stop her. I felt like when i bottomed out in her that she sighed a little ad her pussy relaxed so she could take me more comfortably.
I would love to say that I fucked her for hours that first time and tossed her around the bed whichever way I wanted but the reality was that after hearing her whimper as I fucked her from behind I couldn’t hold on for very long. After a few minutes I could feel that I was about to come and I told her so. She told me she wanted to taste me and asked that I turn her over and come on her. I practically flipped her and after she took me in her mouth again I started to come. She took some down her throat but not very far and I ended up coming on her face, her neck and her breasts. She acted like she had just won a prize and rubbed my cum on her chest and tasted her fingers while looking up at me. I couldn’t help myself and leaned over to kiss her and again tell her how she was a good girl who had just made me very happy.
Source: reddit.com/r/gonewildstories/comments/3x6h65/that_time_i_flew_a_sub_in_for_the_weekend_mf_bdsm
Gives a *whole* new meaning to ‘robin’ the cradle, no? *Pretty hot!*