I'm not a nice person. As I've mentioned here before in this great forum, I've enjoyed sex with older women when I was younger. Maybe it was because it was different, maybe less competition (less baggage, too) that steered me in that direction. Maybe it was the spirit of the chase and that my 'prey' was just as interested in being 'taken', and all I had to do was work a little. Whatever it was, I got to enjoy great sex and fulfill more than a few fantasies. I also became very aware that I developed a 'radar' for picking up when a woman might be open/vulnerable to my seducing her.
This was the case with my best friend's mom. 'Sam' and I had known each other since our sophomore year in high school. We had classes together every semester, worked on the same after-school activities, and even worked our first job together. When Sam had married, and then I shortly after, we double-dated. After my divorce, Sam and I had only sporadic contact. Maybe his wife didn't want him to hang out with a guy who was single, I don't know.
I was in the general area of Sam's old house, and thought of dropping by his mom's home. Sam's dad had died the year before, this I found out from his obit. I sent a card, but didn't receive an acknowledgement.
I stopped in front of Sam's old house. It still looked the same, albeit with some new plants, the garden the same neat and tidy place it was. Sam's mom, 'Helen' was the gardener in the family.
I saw a car in the driveway, and thought that maybe Sam was visiting. I went up to the door and rang the bell. After a minute, I saw the light behind the door's peephole had darkened for a moment. The door opened.
'Well! Look who's here! How are you, X?' Helen gave me a big smile and stepped forward to give me a quick hug. Helen was about 5'3', short blonde hair, blue eyes and wore stylish glasses. She was trim, and always seemed to be smiling.
'Hi, Mrs. Q. I saw a car in the driveway and was hoping Sam might be here.'
'No, X. Sam moved out of state a few months ago. That is his car, but I'm selling it. He told me that he wished he could get in contact with you, but his wife wouldn't be happy about it.'
I told Helen I was glad Sam still wanted to stay in touch, and I would give her my contact information. She invited me inside, and asked if I could stay for awhile to visit. I told her I'd be happy to. She said that she had had lots of visitors after her husband's death (she thanked me for the card), and that life seemed to be progressing along for her, albeit a little lonely at times. She still worked as a secretary for a local school district, and that and her garden and some traveling occupied her time.
She made us some iced tea, and after handing me a glass she sat down across from me.
Why hadn't I ever noticed before that Helen had nice legs? She was wearing what she had worn to work that day, a yellow dress that stopped about the middle of her knees, white sweater, white pumps and tan pantyhose. I told her she looked nice, and she thanked me, and asked her to call her by her first name. 'After all, you aren't a boy anymore, are you?' She smiled, and set her glass down on the end table next to her, and sat back and crossed her legs. I waited for her to pull down the dress, but she didn't, giving me a view of a very nice pair of thighs. I felt an old stirring in my cock, and decided quickly that my visit was going to end with me in Helen's bed.
We talked some more, her dress still not pulled down. She said that she was ready to start dating, but a lot of guys weren't ready to settle down, only looking for a one-night stand. I felt my cock beginning to droop.
'The funny thing is, X', she continued 'that I'm more than ready for some physical affection, but these guys are only interested in their own pleasure.' I felt my prick harden again, thinking that I had a chance to make an easy conquest here. Like I said, I'm not a nice person. I did like Helen, as a person, but I wanted her as a new lover. I didn't know when I would tire of her, but the chase was exciting to me, as always.
Helen got up, and said she would start dinner. She stopped and looked at me, and said 'I'm glad you came, X. It's nice to have company, especially that of a handsome gentleman.' What I was thinking was not gentlemanly at all.
I got up. Helen was still standing looking at me. I approached her. I put my hands on her shoulders, and leaned down to kiss her. Her hands came up and she turned her face away.
'I'm sorry, X. I chickened out. I feel like we could be close and you are a very good-looking man. I imagine making love with you would be exciting, especially since I've known you since you were a boy. It would almost be like seducing you, and the thought of that makes this old broad feel...horny.' She turned bright red at this point.
I reached for her again, this time grasping her arms and pulling her to me. I kissed her gently, feeling her stiffen, then relax. I kissed her again, opening my lips and letting my tongue circle her mouth. She whimpered a little, and then I kissed her harder, poking my tongue into her mouth farther and harder. She started to kiss me back at this point, her arms coming up my back to hold onto my shoulders.
I broke the kiss long enough to remove her glasses, so I could see her eyes better. She looked at me with tears in her eyes.
'I want you Helen. I'll be very gentle.'
'Please, X. I'm scared right now. Don't hurt me.'
'I won't, Helen. I'm just going to make you feel good first, then we'll see what happens next.'
By this time, I had already figured that I was going to have to be the aggressor here, and that I might not end up in Helen's bed, at least not right away. I took Helen's hand, and placed it on the front of my pants, and gently squeezed her hand, causing her fingers to wrap around the shaft of my penis.
'Oh! This is the first time I've touched another man's penis. The only one was my late husband's.' I told her I felt privileged, being only the second man she fondled, albeit involuntarily.
I leaned over and kissed Helen again. She kissed back more readily this time. 'What are you going to do, X?' she asked, sounding a little scared.
'Turn around, Helen.' She did so. I pulled her close to me, lifting up her dress, seeking and finding the waistband of her pantyhose. She gasped, almost pulled away. I pulled her back against me, and put my other hand on the front of her dress, seeking out and the tip of her bra, and underneath it, the nipple, which became immediately erect under my touch.
'Ooh! That feels good, X.' I told her I was glad. I kept playing with the nipple, and managed to work my hand into the pantyhose waistband, and slide it down to her crotch, feeling the now damp cunt hair.
'Uuh. O-o-kay, darling. I-I-think that's enough for now.' I ignored her comment and found her clit. I slid a finger down her slit, and found she was nice and wet. I moved my wet finger back to her clit, and begin rubbing it.
'Oh God. I'm finished now!' she said. 'Be gentle, X. Please, I'm so confused.' Her breathing got faster, as I sped up, kissing her neck. She put her hands up to the arm near the tit I was manipulating, and grasped it. Her hips were bucking now involuntarily.
She was loud. 'Oh, oh, no one's ever done this before! Oh, oh! Oh God! Oh God, help me, please!' She screamed, making me think for a second I had hurt her. I felt her tremble a few more times, and as she leaned against me, I slid my now moist hand out of her pantyhose, and let her wrinkled skirt fall back into place.
Helen turned around facing me. Tears were running down her face. 'My darling X. You have made me feel so good! Please tell me you can stay tonight. I want you to make me feel good again. I want you to...fuck me.' She blushed as she said this.
'One step at a time, Helen. I'll take care of you, dear, and show you how to take care of me.'
For the next 2 months, I spent nearly every weekend with Helen. I introduced her to the pleasure of oral sex, which she enjoyed both receiving and giving. We also fucked madly, including outside in her backyard, something she never considered when she was married. Her favorite activity, though, was masturbation. She loved it when I did what I had done to her the first time, and she always knew how to make jacking me off something I always craved.
I never saw Sam again, and a couple of months after I seduced Helen, she moved in with him and his wife. She wrote me a very nice note, saying that she loved our time together, and was afraid she was falling in love with me, and that it might not end well. She thanked me for showing her how much fun sex could be, and that she had a boyfriend whom she enjoyed shocking with her knowledge. I felt a little envious of him.