My First Time Was With An Older Woman free porn video

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We sat on the couch talking, which was pleasant, but the sexual tension was unbearable. Nancy had turned the TV on when we sat down, which made me wonder what her intentions were. Likely she hadn't made up her mind yet.

Finally, after a short period of silence, we practically fell towards each other. Our lips met in a deep and prolonged kiss. One more thing about her - Nancy was a great kisser.

I began stroking her soft hair while we kissed, and she rubbed the back of my neck. We fell onto the couch and lay down (she lay - I was kind of half-on, half-off; it was a short couch). Lying like this, we embraced. I began nuzzling her neck while her hands went over my back. The TV began playing 'The Star-Spangled Banner' as a sign-off, and Nancy reached behind her and clicked it off without looking away.

This is the one, I thought. After numerous false starts and near misses, I'm finally losing my virginity tonight. With this in mind, I slowly worked my hands down and began caressing her breasts. Nancy did not resist and looked deep into my eyes. Reaching behind her back, she partially unzipped her dress, then pulled it and her bra down, exposing her lovely breasts.

I admired them for just a moment, then began gently caressing them, first running my hands under and over them to feel their softness, then running my fingers over and around her now engorged nipples. Nancy responded to this with increased heavy breathing. I was about to begin licking her nipples when she stopped me by taking my head in her hands.

"Before this goes any farther, I need to tell you that I'm having my period," she said.

I was a little taken aback, and uncertain how to respond. I wanted to have sex with her, but not if she didn't. Clumsily I asked, "Would it hurt you to have sex now?"

Nancy chuckled. "No, of course not," she replied, "it's just messy. Some guys find it a turn off."

I smiled. "Not me. I so very much want to make love to you," I whispered. I then said in a firmer voice, "We could get a roll of paper towels or something, to clean up after."

Nancy smiled broadly and sat up. "I was hoping you'd feel that way," she replied happily.

Nancy stood and led the way into the kitchen. "And we won't have to worry about birth control," she said while taking down a roll of paper towels from its holder beneath the kitchen cabinet.

"So I can go squirt-squirt inside you?" I babbled excitedly, too caught up in the moment to regard what I was saying.

Nancy laughed. "That's one way to put it," she said as we walked into the bedroom.

The room was small. There was a medium-sized table with a sewing machine and pieces of cloth on it. The only other furnishings were a low dresser and a twin-sized bed.

Still yammering instead of preparing for sex with a lovely woman, I asked, "Do you sew?"

"My sister does," she replied as she slipped out of her dress, "this is her house. My son and I live here with her."

"Is she divorced too?" I tactlessly asked.

Nancy looked at me with a hint of annoyance. "I thought we were here to make love," she said.

She stepped out of her dress and took her bra off. Standing there in only panties and pantyhose, she put her hands on my chest and pushed me backward and down onto the bed.

"Sit down, sir," she ordered. She stroked my head and gazed at me, then said, "You get undressed, and I'll be back in a moment."

As soon as she left, I did as I was instructed. I quickly shucked out of my clothes and gratefully stripped off my briefs, which had been painfully containing my erect member. As I sat on the bed, Nancy once again appeared, this time wearing a long bathrobe. To my surprise, she grabbed me by the ankles and swung me onto the bed.

"Lay down, sir," she ordered. I arranged myself on the bed and opened my legs as Nancy was situating herself between them, where she could face my swollen member. I tingled as I anticipated what was about to happen. Smiling, she stroked my member with her hands for a moment, then dropped her head over it, engulfing it with her mouth. There was a soft sucking sound as she worked up and down on my penis, turning her head to-and-fro in a very practiced maneuver.

She transitioned to straight head-bobbing fellatio for a few minutes. I was afraid I would cum in her mouth. Nancy, though, was knowledgeable of these things and stopped in time.

She stood up and untied her bathrobe, then dropped it to the floor. I didn't have much time to enjoy staring at her glorious nudity, for she almost immediately climbed up onto the bed and put her legs on either side of me.

This is it! Here it comes! I was almost trembling with the excitement of having my member in a woman's vagina for the first time. Nancy stroked my manhood for few seconds then, keeping her soft grip on it, raised herself up on her knees and positioned her vagina above my virgin penis.

Nancy took my stiff member and placed it on the lips of her labium. When she lowered her soft vagina over it, I thought I would faint with pleasure. I had never felt something so wonderful. Being a woman of apparently great experience, she quite skillfully fucked me, her breathing coming in small gasps. After some moments, my pelvis began rhythmically rising to meet her up and down motions.

"Oh God, Nancy," I gasped out, "Make love to me - " An inappropriate comment but one that burst from my uninitiated mouth. Finally, I let out some loud moans as my hardness burst and I filled her menstruating womb with my jism.

Nancy smiled broadly and lay next to me, panting heavily. After a moment of recovery, I reached for the roll of towels and tore a section off. I began wiping my limp manhood, while Nancy tore some off and wiped at her vagina.

"Too much of my semen?" I asked.

"Too much blood," she replied, "Even on me."

I rolled the bloody towels inside some clean ones and dropped them on the floor. We lay back on her bed, facing one another, and gazed at each other for some time. I reflected how, even though Nancy was by no means supermodel material, I had never seen a woman so beautiful as one I had just had intercourse with.

At length, she said, "I didn`t know men would ask to be made love to. I thought that was a woman's prerogative."

"It`s from lack of experience," I said, "You're my first time."

Nancy looked at me in genuine surprise. "You're a virgin?" she gasped.

"Well, until about fifteen minutes ago," I replied, then went on, "It hasn't been through lack of trying. I`ve had carnal knowledge several times. But the time was never right. Either the girl was too drunk, not interested enough, or too anxious to get pregnant. But tonight everything was so right. I did so want to make love to you, menstrual flow be damned."

She looked at the ceiling. "I feel like I`ve ruined you," she said at length.

"Oh, that isn't true," I replied, emphatically, "I knew tonight everything was right, and you were the woman I wanted to lose my virtue with. I was anxious for this to happen."

Nancy turned her head, looked at me for a moment, then smiled. "Well, I'm honored to be your first time," she said, finally.

"This is a time I will always remember," I said as I gently stroked her cheek with the back of my fingers. Nancy continued smiling - I thought she might have been purring softly.

At length, I asked, "So, what do you want me to do now?"

"What do you mean?" she answered.

"Well, I know you have a lot of responsibilities, and I don't want to be a bother," I said.

"Do you want to leave?" Nancy asked, frowning slightly with concern.

"No, I don't, I like being here with you," I replied.

"Then stay," she sighed, "I don't have to pick my son up until morning. It won't be super comfortable, but you can sleep here with me. And maybe we can make love again."

"Mmmm...my second time," I grinned.

Nancy grinned back. "I'll make you an omelet in the morning," she said.

 

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Yes, my dream would have been more satisfying if it had gone along the lines of...a voluptuous red-headed noblewoman who lusted after one of her servants. She frequently sent him subtle hints of her desire; brushing up against him as she passed by, bending forward to show off her cleavage, and complimenting him on his strong build (when what she meant was his powerful legs and tight ass). She was sure that he felt the same way about her, as evidenced by his obvious erection during her latest...

Interracial
3 years ago
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Chastity with Ex as Keyholder Part 5

Chastity with Ex as Keyholder Ch. 05bychastity_sissy©Almost every time my Ex had sex with her boyfriend I had to listen. My Ex had decided it was mandatory and would quiz me on how many times she had an orgasm just to make sure I was actually listening, not to mention drive home the fact I couldn't cum.At least, so I thought.You have to understand that not having an orgasm for over a week doesn't sound like a long time, and I'm sure I've gone longer than that without wearing a chastity device....

2 years ago
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Chastity with Ex as Keyholder Part 7

Chastity with Ex as Keyholder Ch. 07bychastity_sissy©The only light came from the crack at the bottom of the floor. I tested my handcuffs as quietly as possible, verifying there was no way to squeeze my wrists out of their cold, metal clutches. I was completely stuck.I could hear my Ex on the other side of the door. She was panting heavily. I could only imagine her Boyfriend's cock ramming her inside and out, over and over again.I guess I should back up just a little bit, although there is...

3 years ago
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Karen an older woman

For as long as I can remember being sexually aroused (this probably started at about age 6) I have been attracted to older women. I'm not sure what got it all started; I do remember accidentally walking in on my mom as a young boy in the bathroom and seeing her bent over toweling off after a shower, totally naked. I was astounded at how big her tits were as they hung down and that she had a hairy pussy and nice soft thighs. Her nipples were brown and actually erect when I saw her. That image...

1 year ago
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older woman

2 yrs a go i met a woman a front off her house she ask me inside. She whas wearing a nice shord dress and highheels. We walked and she ask me iff i whas single and i told her yess i am. Than she told me thats she whas single to. She ask my age and i told her 35 and she ask me how i think how old she is. I anser 30-35. and she started to laugh very hard hahahahaha. NO muchs older she say and i anser 40. she say again NO and say thats she is 49 yrs. And i told her thats she look still so thight...

2 years ago
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My Sex Journal pt6 Older woman

Read my previous stories for this to make more sense. You will find them on my profile page. Please rate and comment, let me know how I am doing.I'm going to skip ahead a little now to when I was just under 18. As soon as I turned 16 I left care completley, turning down all offers of living assitance so I spent the next 16 months or so moving around from place to place where ever I could find a bed and a bit of work and sometimes sleeping rough. It's a time of my life I don't think fondly of...

1 year ago
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BBC losing virginity to fat older woman

Ever since I was a young boy, I have had a condition where my dick would suddenly get hard and grow like crazy. Some days it would only happen once a day and other days it would happen up to 4 or 5 times a day. It didn’t really bother me at a young age. Sometimes my dick would get so hard that it did hurt a little bit, but it would never last for very long, so I never had to pay to much attention to it.It started getting worse when I was 14 years old. I don’t know what triggered it, but I can...

1 year ago
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An Eighteen Year Olds Affair with an Older Woman

Amy and her husband Mark had just moved to a new community several hundred miles from where they used to live. Mark was a pharmaceutical salesman, and this was their third move since they had been married fifteen years ago. They hoped this would be their last move, since they didn’t want to move their only daughter to another school. Amy had recently turned forty and was a bit on the conservative side. She was a beautiful looking woman; she had long blond hair which flowed down her back while...

Cheating
1 year ago
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The Keyholder Pt 3

The weekend in Paris had been fantastic, three whole days with Amy plus three consecutive nights of release. Returning to work had been hard, not least because he had now spent five continuous days inside the locked chastity cage. Nights were particularly hard as his cock had started to expect freedom. In the early hours it would throb and the pressure inside the cage would build. Ben would wake up and massage his balls while he watched his helpless red straining cock try to squeeze through the...

BDSM
2 years ago
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Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

4 years ago
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Cumming inside an older woman

When I was 34, I dated a 40 year old Puerto Rican woman I met through work. Getting alone time with her proved difficult, though, as she had three kids who, understandably, took up most of her time. When we did manage to have sex, it was epic – she had a body very much like Jennifer Lopez, so needless to say my mind fantasized a lot while we fucked! Sometimes we would go weeks without having sex, and this really bothered me. I didn’t want to be the guy who complained about it because her kids...

3 years ago
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I lost my Virginity to an Older Woman

Part 1: SpainThis is the story of a journey. It started in Spain, continued in France and finished (climaxed?) in London. It was a journey of discovery. This was when I first discovered the thrill of intimacy with a real woman. This was when I lost my virginity.This is a completely true story. It happened over 50 years ago but I can remember much of it as if it happened yesterday. (I have used a little “artistic licence” in filling in memory-gaps with actions that probably happened, anyway.)...

1 year ago
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Cumming inside an older woman

Sometimes we would go weeks without having sex, and this really bothered me. I didn’t want to be the guy who complained about it because her kids were definitely more important but masturbating alone at home just wasn’t satisfying enough. I wanted that physical contact with someone. One night, after almost three weeks with no sex, I turned to “Old Faithful” – the Quest chatline, hoping to at least have phone sex with someone. I’d had moderate success with Quest previously – a few threesomes, a...

2 years ago
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Sex education from a much older woman

I have for some time been writing about a relationship with my partners, 76 year old, Aunty Jean and her daughter Jane. I feel it is time to commit to paper how my attraction for much older women started some 31 years ago when I was 19. Like a lot of young men of that age I was obsessed with girls and sex and spent most of my waking life thinking about and trying to get plenty of the latter. Having been brought up in a morally strict household the opportunities were few and far between and thus...

2 years ago
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An Older Woman

Introduction: Mature office lady gets some attention An older woman We were having lunchtime Xmas drinks on Friday at work to wrap up the end of year which was good as the holidays were approaching. I work in a small group with 3 guys and our customer service lady Paulene. Shaun and Paul are 33 and I am 29. I dont know how old Paulene is but she could be early fiftys possibly. She only works part time and I always look forward to the days that she is on, as I sort of fancy her, even though...

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