I told her it felt fantastic. She asked me if I'd like her to press inside. I said that was maybe a step beyond normal, but she argued that everything's normal and I shouldn't be so inhibited. And then she pressed her finger into my ass, anyway. Oh man, it felt so good. She just went in and out a little and I began to move my ass up to meet her finger... it made my hard cock rub against the sheet. She brought me close to getting off a second time. Then she pressed in harder and it started to hurt. I squeaked and pulled away from her finger. She stopped and told me we needed lubrication - which I didn't have. She said we could try again the next time we got together, if I wanted. I definitely wanted, and told her so. I was so excited to be trying something completely new to me. She was definitely enjoying being some kind of sex-guru to this naive small-town boy.We arranged for the next night, again at my apartment and I went to a drug store the next morning and bought KY jelly.. She spread a large quilt on the floor and told us to undress and lay down on our backs. We didn’t argue. She was unusually assertive, Jan is normally quite quiet, but she was in a role here she had considered carefully and we had agreed how we wanted proceedings to go. If she felt uncomfortable at any stage she would let us know and that would be it, but she was clearly enjoying herself currently. “One of you boys is going be lucky tonight and one not quite so lucky” She opened her silk dressing gown and stood over us. She was putting on a pair of long black velvet gloves. “I need just one man tonight and he needs to have good stamina so I am going to see which of you can last the longest. Whoever comes first will have to go home or up to bed, is that clear?” It was perfectly and I had already agreed to take the position nearest the fire place thereby having her use her right and stronger hand on me. She knew how to wank my cock to perfection and I had abstained from sex for a good.
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