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My husband and I both lost our first spouses. My husband was in a fatal car accident and Jason's wife was taken by cancer. My stepdaughter, Katie, was young when her mom passed. She and I grew close and I was a friend and confidant as well as a parent to her. We confided in each other on many topics, including love life and sex life - particularly after she lost her virginity.
During her senior year of high school, shortly after she turned 18, she started dating a 19 year old young man. He seemed like a nice enough guy. Jason liked him. Katie was worried that he was just into her because she would put out. She wasn't ashamed of her reputation, but wanted this boy to really like her, as she thought he was pretty special. She denied him at every turn, even for hand jobs or blow jobs, let alone actual fucking. Jack seemed to stay interested in her, even though he wasn't "getting any."
One night, while Jason was out of town, Katie came into my bedroom to talk to me. She said she was ready to sleep with Jack. She was just worried that he might not be good in bed. Why was a great guy single? Was it because he didn't know how to fuck or please a woman? We had a long conversation and I told her that I would take care of everything.
The following Saturday afternoon Katie was at work. I had her text Jack and tell him to come to the house, as it was an emergency and she needed to see him. Of course, Jack arrived in short order. I was waiting for him with me trap ready to be sprung. I was dressed in a white shirt dress that maybe reached mid-thigh. Under it I wore a sheer matching bra and panty set with a garter belt and seamed stockings. I was in white heels. Jack was dressed like many 19 year old boys on a Saturday. T-shirt and jeans. The jeans were baggy. I could see the waistband of his boxers.
I invited him in and led him to the leather sofa in the living room. He asked about Katie and said he told him it was an emergency. I assured him that Katie was not home. I told him that I wanted to see him. He looked around and seemed confused. I told him, once again, that Katie was not there.
As he sat on the sofa, I sat and turned towards him, my right knee against his leg. I placed my fifth hand on his knee and he nervously looked at it. I said, "Jack, you are here today because Katie really likes you." He replied that he really liked her, too. I then told him, "I know that Katie has not let you do things sexual with her yet. We are very close and share everything." I could see Jack swallow and his eyes go wide. "Jack, how sexually experienced are you?" He replied that he had been with a couple girls but a number of times with each. I asked, "Jack, did you pleasure these girls? Did they cum from what you did?" The young man was astonished at my line of questioning. He stammered out that he thought they enjoyed it every time.
I stood up and started unbuttoning my shirt dress. I looked him straight in the eye and told him that I have to approve of him before Katie would touch his cock or suck him or let him in her pussy. As my body was exposed I could see a nice-sized erection showing through the denim of his jeans. I slid the unbuttoned dress from my shoulders and let it slip to the ground. I stepped out of it and kicked it aside. I asked, "Jack, do you like what you see?" He simply nodded with his mouth slackjawed. I cupped my small B-cup breasts and tweaked my prominent nipples through the sheer cups of my brassiere. I kept a serious look on my face and I could tell he was nervous. I nodded at his crotch and said, "Show me." in a calm yet demanding voice.
Jack unbuttoned his jeans and slid them down to his knees. His boxers came with them and a nice, thick erection sprung forth. I nodded approval, not yet smiling though I was definitely smiling on the inside.
"Stroke it for me." I said. I turned and walked. My heels clicked on the hardwood floor. I was thinking to myself that if this lad is any good at all with that hunk of meat, my Katie will more than enjoy herself. At the end table I picked up a pack of cigarettes and a lighter. I pulled one out and lit up, exhaling upward. I strutted over to an easy chair and opened my legs wide, over the arms. I used my free hand to call Jack over to me with one finger. He slipped his jeans and boxers off and stood before me. I didn't say a word. I took a long drag and exhaled at him before motioning for him to remove the rest of his clothing. The young man quickly complied. I could see pre-cum at the tip of his penis. I continued to smoke my cig as my free hand rubbed my nipples. My hand snaked down my abdomen to my panties and inside. He could see my fingers through the sheer material as I parted my labia. I let out a sigh as I touched myself.
I withdrew my hand and told Jack, "If you don't impress me with your cock and your abilities, you will not be with my stepdaughter. You had better last. You had better make me cum. Do you understand?" He was wide-eyed as he nodded and said, "Yes, ma'am."
I pointed to the floor for him to kneel and then pointed at my pussy. "Eat me darling. Make me wet for that fat cock of yours."
Jack quickly fell to his knees and crawled between my spread legs. He licked me though the dainty material before slipping it to the side and and licking my outer lips. He then parted them with his tongue and held them apart with his fingers as he zeroed in on my pussy opening before flicking my clit repeatedly, making me illicit moans of pleasure. I reached over to an ashtray and put out my cig before putting one leg over his shoulder. My heel dug into his back and I could see him wince. My fingers from both hands clutched his hair and pulled him tight to me, forcing greater contact between his lips and tongue and my genitalia.
I started humping his face as I got into the pleasure he was providing. Orgasm hit me and I rode waves of pleasure up and down as he continued to assault my clit and pussy. He had two fingers twisting deep within me while his lips sucked my clit and then he licked it with broad strokes, the coarse surface of his tongue sending me to the moon in orgasmic bliss.
I pushed the young man away and then told him to show me what he could do with that cock. He stood up and lined himself up with my slippery opening. He rubbed his head up and down the seam of my slit before pushing into me deeply with one thrust. I grunted as he was in me to the hilt. He began to slowly thrust into me and picked up the pace rather quickly. I ordered him to slow down so he wouldn't cum to quickly. I told him to lie on the floor. I stood over him and lowered my cunt onto his throbbing pole. I controlled the action this time. I was edging him. I was talking to him the entire time, explaining what I was doing and how he would last longer, have greater pleasure, and bring greater pleasure to the women in his life.
Jack massaged my breasts. I removed the flimsy bra and helped him pinch my nipples which made me shudder and moan. I began grinding my clit against him as he was thrusting into my hole. My long, painted nails were dragging across his chest providing erotic stimulation through light scratches.
I could sense that Jack was not going to last much longer. His breathing was more ragged. His eyes were glassed over. His moans were more guttural. I felt a rumble deep within his being and he groaned as his hips pushed me up off him. I slammed myself back down as his cock spewed countless streams of his hot cum deep inside me, with in turn caused me to shake uncontrollably as I hit another orgasm and was cumming repeatedly on his thick cock.
Eventually I fell to one side and his cock fell from my slit. His seed started oozing from me. I reached down and put it on my fingers and fed myself. "Mmmmm" I said, "So delicious. I love hot cum from young men."
I kissed Jack and told him that I approve and that when Katie gives the okay, he has my blessing to fuck her. I also told him that this was not the only time he was going to pleasure me. I guaranteed him of that.
I got up and told him to dress and leave. I picked up my dress and went up to my bedroom. I sent a pic of my cum-leaking pussy to Jason and texted Katie that I definitely approved of her fucking Jack.
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