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One of my most vivid memories to jerk off to when my wife isn’t interested in sex was my time with Darlene. It was my first and only time with an older woman.
I was in my late 20s, 5-foot-8, a little overweight, not muscular, short brown hair, brown eyes, glasses, shy, and not confident in myself as I had only been with two other women prior to meeting her. Darlene was divorced, in her early 50s, black hair, baby blue eyes, 38Cs and a shapely figure.
We had met in an online music forum. She lived several states away, but had friends about an hour away from me. So one summer she said she was coming down to visit her friends for a week and said she wanted to arrive a day or two early to hang with me. I didn’t think anything was going to happen. But I was wrong.
When I picked her up at the train station, she greeted me with a big hug and an open-mouthed kiss that had her tongue dancing with mine. She held my hand as I carried her suitcase out to the car. At the car gave me another hug and open-mouthed kiss. She said she liked public displays of affection.
Being inexperienced, I still wasn’t sure where things were heading. I didn’t know if she was being overly friendly or was trying to put the moves on me. But once we got back to my place we continued to hug and kiss passionately while fully dressed. All this kissing had an effect on me and I developed a hard-on. I asked her if she minded if I took it out as it was getting tight and uncomfortable in my pants. She smiled and said she didn’t mind at all and started to stroke me while we kissed. Foolishly I didn’t try to undo her bra, feel her up or put my hand in her pants as I was still unsure of what was happening and afraid a wrong move would ruin it all. I just hugged her, occasionally moving my hand down to squeeze her ass.
This lasted about 30 minutes before it was time for us to head out to dinner and a show we had plans to see. I pleaded with her to finish me off with her mouth or her hand and not leave me this way. She laughed and said “we’re not teenagers and you won’t have blue balls, if you want relief finish yourself off”
I said “Ok, but can you get next to me while I do it?” She said yes and sat next to me on the bed while I pulled my pants down and started to beat myself off, stroking my hard six inches fast. She was looking at my cock intently when I came hard shooting spurts of cum high in the air.
She said “wow, I don’t think I’ve ever seen anyone shoot that high before”.
I joked with her “do you want to clean me güvenilir canlı bahis siteleri up” and she said “no” and I cleaned himself up, got redressed and we went out and had a nice dinner and enjoyed the show.
When we got back home and got changed for bed, I threw on a pair of silk boxers and an old t-shirt. She put on a bright red silk teddy with a plunging neckline that showed plenty of cleavage and in terms of length, barely covered her ass. S
She laid down in bed, smiled and asked “how do I look?” I slid in next to her and said “fantastic” and seeing her dressed way, my earlier inhibitions were gone. I wrapped my arms around her and plunged my tongue into her mouth. For the next few minutes we kissed passionately – our tongues not leaving the other’s mouth while rubbing our hands on each other’s backs.
Then I decided to get bold and licked my way down her neck and into her cleavage while moving my hands down to rub her ass through the silky material. She moaned “yes” and ran her hands through my hair. A minute later she peeled off my shirt and we resumed kissing as she reached down and started to stroke me. I responded by starting to finger her, slowly at first. Letting my fingers do the walking as I rubbed her labia gently. Then more rapidly before sliding a finger inside her. She licked my neck moaning “that feels so good” and started stroking me harder as my cock reached maximum hardness and length. I slowly peeled off her teddy and with her nakedness on display started to lick my way down her body, pausing to suck on each breast, taking the nipple between my teeth and flicking his tongue over it. Then I licked my way lower until my face was between her thighs.
I slowly licked between her lips, savoring her juices, before focusing my efforts on having my tongue probe for her cilt while finger-fucking her slowly. She put her hands in my hair telling me how good I was. After 15 minutes of moaning in pleasure she pushed my head away and said “my turn”, sat up and pushed me onto my back. peeling off my boxers.
She slowly, teasingly licked her way down my body until getting to my cock. She slowly licked her way up and down it, running her tongue over the tip while caressing his balls before lowering her mouth down over the entire length, gently scraping her teeth along it’s length as she went down. She bobbed up and down like this for a few minutes. Then she switched and started stroking my wet cock with her hand while running her tongue over my balls before sucking them into her güvenilir illegal bahis siteleri mouth one at a time. The previous women I had been with weren’t good at giving blowjobs, but she had me in heaven. She then returned her mouth to my shaft and her head was bobbing up and down slowly and beautifully, giving me intense pleasure. I ran my fingers through her hair and moaned “oh god, that feels amazing, but please stop, I don’t want to cum yet”.
She released my cock from her mouth, looked up at me and said “I want to feel you explode in my mouth, so you better give it to me” She then went back to sucking my cock, looking up at me pleadingly with those baby blue eyes. After another minute of sucking me while rubbing my balls I moaned “oh god, I’m cumming” and held her head in place as I fired what felt like endless streams of cum into her mouth. She looked up at me, with cum dripping out of the corners of her mouth and said “delicious, now let’s get some sleep”
We fell asleep naked next to each other, almost spooning, with me behind her, cupping one of her breasts. A few hours later Darlene woke up. She reached behind her and started stroking my cock back to hardnesss. She rolled over, gave me a big open-mouthed kiss, and said, “I hope you’re ready, I need to ride this thing hard, where do you keep your condoms?”
I rolled over, reached into the nightstand and grabbed one and handed it to her. She quickly opened it, rolled it down my length and said “get ready for some fun”
She positioned herself over it and slowly slid down my thin six inches until it was all the way in. She started to slowly lower herself up and down on it, telling me to sit back and enjoy. She started to pick up the pace and the site of her bouncing breasts became too much for me to just be a passive participant. I sat up at an angle so she could ride me while I sucked on her breasts. I also started to gently thrust my hips up on her down stroke. Her gasps of pleasure were really turning me on and I wanted to give it to her missionary before I came.
So I said “my turn” and rolled us over so she was on her back with her legs on my shoulders. I started to thrust into her hard and fast and she just alternated between moans of pleasure and grunts of “yes, give it to me hard”. When I moaned I was getting close, she slid her legs down my body and wrapped them around my waist and ass to hold me in place deep inside her as I came. A minute or two later, as we were catching or breath, I pulled out and peeled the condom güvenilir bahis şirketleri off and she said “let me clean that up for you” and proceeded to lick and suck my cock clean.
We fell asleep in each other’s arms. The next morning, I was the first one up and proceeded to give her a wake-up call by burying my face between her thighs. I slowly licked my way up and down her pussy lips, slowly sliding my tongue between them. She was getting wet and I loved the taste of her juices. I used my tongue to trace the alphabet on them and slid a finger down to rub her clit while my tongue probed deeper. I kept up my oral assault on her until she had two orgasm and my face was wet with her juices.
After that we grabbed another condom and headed for the shower. In the shower we soaped each other up. After she ran she hands all over my chest to get it soapy, she gave me an amazing handjob, gripping me just right and stroking me at just the right speed to get me rock hard. While she did that I rubbed and sucked her breasts while fingering her pussy. She got on her knees and proceeded to suck me for several minutes as the water cascaded down on us.
She then stood up, grabbed the condom and slid it on me. She turned her back to me, leaned against the wall, looked over her shoulder, smiled, and said “give it to me hard big boy” and bent over.
I stepped up behind her and swiped my cockhead over her pussy lips a few times before she started to push back at me, urging me to get inside her. I took my cock in one hand, lined it up, and slowly slid into her. Once in all the way I grabbed her hips and started to pound her with hard, steady strokes. Our mutual moans of pleasure echoed off the walls as the water poured down on us. I slid my hands up to her breasts and squeezed them tight as I continued my tempo of hard, slow, steady strokes. She begged me to go faster and I slid my hands back down her hips and obliged thrusting hard and fast.
After a few minutes I groaned I was coming and thrust into her as hard and deep as I could. She shrieked with joy as an orgasm racked her body as well. We stayed like that for a few minutes – she leaning over in front of me hands on the wall while I leaned on her, my head on her back, my hands on her hips and cock inside her – as we caught our breath. She then eased the condom off me and gave me a soapy handjob.
“I don’t think I can get it up again,” I said.
“That’s okay honey,” she replied. “This has been the best sex I’ve had in years. We still have all day and all night to do it more.”
“This is the best sex I’ve ever had,” I replied. “And yes, I hope to be doing you more times and in more positions as the day and night go on.”
“Thank you for the complement honey,” she said. “Yes, I will be your teacher and we will be fucking in many more positions later on.”
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