Note: This story was dynamically reformatted for online reading convenience. To say that Richard intrigued Allison was to put it mildly. She was no innocent, having lost her virginity right before he sixteenth birthday. And she had done some things in her sex life that she considered offbeat. She had used, and had had used, vibes and dildos on herself, had tried anal, and had done a bit of exhibitionism. Of course, there was the spanking with Tony. But the BDSM aroused her, and being controlled by a much older man, for some reason, gave her a bit of a thrill. So she agreed to allow Richard to call her and she would take it from there. Richard had called her twice. Both conversations were pleasant, and dealt with likes and dislikes. Richard ended each conversation with a simple "When do I get to spank you?" As they live about two hours apart, meetings would be difficult. The two finally agreed to meet at Karen and Frank's for dinner one Friday evening, right after the Fourth of July. It was to be a relaxing, friendly, and casual dinner. Allison wore a white golf t-shirt and a pair of jeans. She wanted to get to know Richard a bit more, and did not want to come across as cheap. The dinner was sociable with minimal conversation about BDSM. Near the end of the meal, Richard asked Karen if she wanted her bottomed warmed a little, and, with the encouragement of Karen and Frank, agreed. She went over Richard's knee for the first time. The spanking really wasn't all that much. Some swats over Allison's jeans with Richard's hand, followed by an occasional rub, and lasting roughly thirty minutes were the sole content. Of course, Karen and Frank watched. And Richard, it seemed, was good at keeping Allison off-balance. He did not spank with a regular rhythm; instead, he alternated varying numbers of strokes and rubs. Karen and Frank enjoyed it, and being caught off guard excited Allison. As for Richard, this was all quite mild. But he was enjoying himself. And, going on his instincts, which were correct, the girl was enjoying it and was pliable. He decided he would encourage another spanking and make it a bit more risky. The second spanking took place two weeks later. Richard had come to visit on a Saturday night, and taken Allison to dinner. Allison wore a simple light-blue blouse and a jean skirt, which came to just above the knee. She wore a matching white bra and string bikini panties for lingerie. Richard dressed casually. They went to a nice Italian place that Allison had eaten at before, had a long, friendly dinner, and gave the appearance of a father or uncle having an evening out with a niece or daughter. After dinner, it was still early, so the pair went back to Allison's apartment. The roommates were away again for the weekend, so Richard and Allison had the place to themselves. The two talked and listened to some music, and Richard turned the conversation to the first spanking. Allison blushed and said that she had enjoyed it, so Richard suggested another. Allison agreed. The spanking, once again, was basic and simple, with Richard pushing it up a step. He began with a few hand whacks, with Allison over his knee. Then he hooked her left leg with both of his, forcing her thighs apart a bit and keeping firmly over his knee. He yanked her skirt over her hips and gave her five quick whacks, over panties, on each cheek, followed by some nice rubs. Allison didn't know whether she was more shocked by the spanking or by her skirt being over her hips. Richard's hand stung, and she squirmed and wiggled with each swat. The rubs, however, felt very, very nice. She also felt somewhat embarrassed being over this older man's knee, he legs and backside exposed a bit. What shocked her was that this was beginning to arouse her. Richard finished his rubbing, the informed Allison that a few more were in order. He grabbed the top of her panties, gave her a very tight wedgie, and proceeded to smack away with his right hand on the girl's bare cheeks. The girl gasped, gave out with some loud squeals, and squirmed and wiggled on his lap. When her bottom was a nice pink, Richard rubbed some more, still keeping the wedgie in place. Allison was humiliated, shocked, and aroused by the whole thing. Richard rubbed her bottom, occasionally caressing a hip or the inside of a thigh, and made small talk with the girl for about ten minutes. She really liked this play. When he was finished, he let Allison up, talked to her a bit more, told her he would call again, and gave her a few swats for good measure on her backside. She gave him a soft kiss on the lips, and the two parted. Richard knew that she loved every minute of it. The third spanking took place two weeks later, once again at the apartment. Allison could hardly wait. Thinking of the coming weekend, she would get wet. She was very, very curious as to what Richard would do next. If he wanted to fuck, so be it. She would be willing. Their age difference would not matter, nor would his looks. The second spanking had gotten her warmed up. Once again, they went to dinner. Allison wore plain khaki slacks and a blouse. She had put on a pair of novelty panties, however. Pale yellow string bikinis, full bottom, with black trim and smiley faces all over covered her womanhood. She wanted to get Richard's reaction. Allison had no clue that he had a panty fetish. Richard, on the other hand, had plans to push the spanking a bit more. He remarked at dinner that it would be tough to spank her over the slacks. She giggled and said that she would take them off. After dinner, Richard and Allison headed back to the apartment. They talked a bit, Richard gave her some bottom smacks, and they decided to begin the spanking. Allison liked to show herself off, so she took off her sandals and khakis and offered Richard some wine. Richard took a look at the panties, agreed to the wine, and decided she was ready. He gave her a few smacks on the backside and sent her off to get the wine. As she handed Richard his glass, Richard inserted an index finger into the waistband of the panties, remarking how lovely they were. Allison giggled. Richard traced a few lines around her hips, his fingers inside the waistband, and then finished his wine. He ordered Allison over his lap for wearing naughty panties and proceeded with his hand spanking. Richard gave her a good ten-minute whacking, and then removed the panties. He said they were only getting in the way. Allison blushed, but was excited and made no effort to stop him. He gave the girl a few more smacks and then began rubbing, calmly suggesting that they try something different. Allison agreed, thinking that it was going to be lovemaking. Richard had brought a small backpack into the apartment. He had Allison stand, gave her a few smacks on her bare bottom, and removed something from the backpack. The something was a brown leather strap, about two feet in length, and invited Allison to try it. Allison gulped. Richard gently rubbed the strap over Allison's naked backside, and began to unbutton her blouse. He told her she would like the strap; it was gentler than his hand. He finished unbuttoning her blouse, removed it, laid it on the sofa, and gave her some gentle taps with the strap on her bottom. Allison, wearing only her bra, blushed. Richard gave her a few more taps and suggested that she get on all fours. Allison complied. Richard then knelt on her left side and began to smack her naked bottom, omitting the hand rubs after a number of smacks. Allison felt humiliated, embarrassed, shocked, and was quite wet. She squirmed and rocked with each swat. She hated to admit it, but she was enjoying herself. The strap didn't hurt as much as his hand, but it did give a sharp sting. And she began to feel warmth spread throughout her abdomen. Richard gave her a few good swats and smiled at the lovely pink color spreading over her bottom. He paused; laying the strap on the small of her back for a second, and then began to gently rub it over her backside. He smiled with approval when he ran the strap down the crack of her backside, teased the inside of her thighs a bit with it, and then rubbed it in between her legs. The girl was squirming. Allison was starting to pant. When Richard teased between her thighs with the strap, she thought that she would die. She now understood what Karen meant when Karen said that Richard was very, very good. Richard gave her three more hard swats on each cheek, and then had her stand in the center of the room, legs spread, and hands on her head. He noticed she was blushing and was looking away from him. He decided to humiliate her a little more, remarking on her lovely landing strip. Allison thought she would die. Richard rubbed her backside with his hands for a few moments, and then suggested she go into the kitchen and get a chair. When she brought the chair back, he had her place it in the center of the room. He had her lean forward, hands on the seat of the chair, and spread her legs. Allison thought she would cry. Richard was teasing her like crazy. And she was loving this! If only Tony would have done something like this to her! She shivered, swayed, rocked, and actually bounced on her feet and danced with each swat. Richard gave her ten on each cheek, delivering three or four at a time, and separating the groups of swats with some hand rubs and teases with the strap between her legs. Once her even tickled over her mound with his fingers, which made her gasp and shiver. Richard finished up the spanking and had Allison take the chair back into the kitchen. He ordered her to refill his wine glass, and then stand in the center of the room, hands on head and legs spread. He put the strap down, stood behind the girl, and examined his handiwork. Allison was standing there shivering, very aroused, and quite exposed. Her backside was a glowing pink and very, very warm. Richard gave her some rubs on her but cheeks, very gently, and then sipped his wine and moved in front of her. He told her she was lovely, and could probably take a lot more. He tweaked her nipples through her bra and asked her if she had liked it. Allison really was in no position to disagree with anything. She was almost naked, soaking wet, and shaking like a leaf. She was almost ready to climax. She told Richard that yes, it was wonderful, and he could do more if he wished. Richard merely smiled, traced a line with his fingers from her chest down to her stomach, and began to gently play between her legs. He teased her until she was almost ready to climax, and then stopped. He finished off his wine and told her he had other surprises for her. Oh, and for her next spanking, she would be completely nude. Allison stood there, shivering and shaking, wanting desperately to climax. Instead, Richard put his wine glass in the sink, packed up his strap, and walked out of the apartment! Allison waited until she heard the door lock, ripped off her bra, and ran into her bedroom. She found an old vibe and masturbated, climaxing intensely. And then she masturbated a second time.