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I Want to Sleep With An Older Woman

Personal Stories, Advice, and Support 87 People

    It Can Happen

    Lots of older women would love the attention of younger men! But as they get older they want to have sex with "Friends" not just guys showing up -getting thier rocks off & leaving- they prefer friendships& doing more than just sex! Plus most folks don't get prettier or...
    jettys jettys 56-60 Sep 20, 2011

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    Nurse Alert

    I work with several nurses that are older than I, I am am 38 year old and they are in their late fifties and early sixties. They do take care of their bodies and are into Yoga. The two that I am interested on are both single and usually make comments about my looks and wonder...
    ppdap ppdap 36-40, M 2 Responses Sep 15, 2010

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    Looking For Greek Woman Or Cpl

    i want t sleep an older woman married or not !!!! older women is perfect for hard sex
    Kostas30 Kostas30 31-35, M Jul 9, 2011

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    As I Mature, My Interests Are Changing

    I am 32, and I am finding that the more I mature, so do my interests.  I am finding that more and more I would love to sleep with, and learn from the experience of, an older woman. Any women in the Philly area that want to teach a younger man?  email me at...
    daringtrucker daringtrucker 31-35, M Jan 10, 2010

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    Related Experiences

    I am in love with a woman that is 14 years older than me her name is stargazer gal she is the very essence of what makes me want to live with out her it would be like living with...
    cassiescowboy cassiescowboy 26-30, M 1 Response Jul 13

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    My older sister's friend gave her a stuffed puppy and I stole it from my sister when I was like 3. I slept with it every night. I even gave it a name... Puppy. XD Haha, don't judge...
    Yasmin8 Yasmin8 13-15, F Jul 4

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    I used to sleep with a stuffed pink elephant and then I grew out of it.. Then two days ago I got a stuffed turtle.. Now I sleep with it and I can't sleep without it.
    ImNotOkayWhyCantYouSeeThat ImNotOkayWhyCantYouSeeThat 13-15, F 5 Responses Jul 2

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    Man I'm just chilling here with my dad's friends, it's nice interacting with older. People who run a business or talk about work
    baconassassin baconassassin 18-21, M 2 Responses Jul 18

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    All I have thought about lately is how I want to please a woman. How as much as I want to be sweet and sensual with her I want to f*** her silly with a strap-on. I want her...
    shygirl2014 shygirl2014 26-30, F 2 Responses 5 days ago

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    I sleep with a stuffed Velveteen Rabbit. The whiskers have all fallen out... Been pulled out... And it has a wrinkle under the straight mouth so it looks like he/she is smiling...
    Liddledame Liddledame 31-35, F 2 Responses 2 days ago

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    **** i sleep with my panties on its comfortable and it doesnt matter what season i can be freezing cold and i'll still go to sleep with panties and a tank top the most comfortable...
    ihaveaname99 ihaveaname99 13-15, F 2 days ago

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    Ive always wanted to be a woman but have been too afraid to tell anyone. I secretly cross dress but want to buy more womens clothing and find a guy who likes tgs. So scared to come...
    sissboy25 sissboy25 16-17, T 1 Response 21 hrs ago

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    I'm afraid of sleeping with my bedroom door open because I feel like someone or something is going to walk by my room at night or watch me sleep
    LilVixenClaire LilVixenClaire 18-21, T Jun 29

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    I'm 21 and still sleeping with my childhood stuffed monkey I had it since I was a baby. I feel like a kid again holding it while I sleep
    Guywhopees Guywhopees 18-21, M Jun 30

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    I have a giant stuffed bear that I sleep with that reminds me of my brother. I only sleep with it when I miss him though (He lives in Georgia, I'm in New York)
    aurorad19 aurorad19 13-15, F 1 Response Jul 3

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    Hahaha, well if having them all sitting on the end of my bed counts, then yes, I sleep with a LOT of stuffed animals. xD If we're talking snuggling things, then I have a real cat...
    randomlygenerated randomlygenerated 18-21, F Jul 5

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    I cannot sleep without my fan on! Its just impossible. If i even attempt to i can't get to sleep. Just not gonna happen
    CPrimer CPrimer 18-21, M 1 Response Jul 8

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    I used to always sleep with it cracked open but now I sleep with the door closed and locked. It's not like I have to have it that way but I prefer it because it guarantees my total...
    Darkanddesolate Darkanddesolate 16-17, F 2 Responses 6 days ago

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    I'm almost 20 and I sleep with a teddy bear everynighy. my bf gave me it and I love it. Idc how old I am it helps me sleep.
    PrincessDemeter PrincessDemeter 18-21, F 1 Response 5 days ago

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    It just gets too hot with pants on when I sleep! Plus, it can be fun when having a sleepover with my boyfriend. ;P
    yougoglenncoco yougoglenncoco 18-21, F 1 day ago

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    I must have my door closed at all times. I just really love my privacy. Whether it's day or night, it has to be closed, especially at night, I can't sleep with my door open.
    DiamondInTheSkye DiamondInTheSkye 18-21, F 2 Responses Jun 29

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    I sleep with a stuffed turtle and love pandora&earbuds so, It's a 'cuddle-a-stuffed-turtle-&-destroy-ur-hearing' day, who is in?
    ImNotOkayWhyCantYouSeeThat ImNotOkayWhyCantYouSeeThat 13-15, F Jul 5

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    I absolutely adore sleeping with stuffed animals! I have a light blue bunny my mom have me when I was younger. She passes away in 9/11 so it's the last thing that I have of her. I...
    WisdomTree WisdomTree 18-21, F 2 Responses Jul 5

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    I Dont Sleep With Pants Or P J Bottoms On mostly because of my phantom night turds I just put a tarp on my bed
    mcfartcloud mcfartcloud 31-35, M Jul 7

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    Sometimes I sleep with nothing on, is that weird? I'm only 17 years old.
    WillsWill WillsWill 16-17, M 2 Responses Jul 10

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    SLEEPING WITH SIRENS AND PIERCE THE VEIL ARE GOING ON TOUR TOGETHER WHAT IS MY LIFE EVEN<33333
    xxxalyssabrownxxx xxxalyssabrownxxx 13-15, F 1 Response 6 days ago

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    I have a stuffed bear named Barry and he is about 12 years old and I sleep with him every night except when I wake up he always ends up on the floor and I have no idea why.
    michelleviktoria michelleviktoria 13-15, F 1 Response 4 days ago

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    I sleep with a wolf lol.....
    Midnightthealphawolf Midnightthealphawolf 13-15, F 4 days ago

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    I'm a city girl, yet I cannot sleep without the soothing sound of a fan on medium no matter where I am. Can anyone relate? :)
    OceanicXs OceanicXs 26-30, F 16 Responses 1 day ago

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    I love my wife but I would like to be with another woman for a night
    nativecock nativecock 41-45, M 1 Response Jul 19

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    Any girl want this with a big guy ?
    scottishbigguy scottishbigguy 22-25, M Jul 19

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    I am only 13 but I want one sooooo bad! Not for sex. Just long distance dating. Ocasional video chatting on Skype or Facebook. Most of the time just text chatting. I need a woman...
    TreeSmasher TreeSmasher 26-30, M 4 Responses Jul 14

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    I just want to hold and be held by a woman. To be loved, cared for, you name it. And, sadly, I'm 47. My time is running out. Not due to life threatening illness ; just getting...
    BuckeyeNut1967 BuckeyeNut1967 46-50, M 1 Response Jul 19

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    I have a severe crush on one of my old friends mothers. I knew her when i was bery young but i met her again recently and she's all i can think about. She is widowed and i don't...
    James5946 James5946 18-21, M 4 days ago

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    I really want to be with a milf. There's something so sexy about an older women.
    smokesomething smokesomething 18-21, F 1 Response 2 days ago

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    I was involved with the mother of a friend of mine. He never found out. It was very complicated because she became a widow suddenly. It was all very tragic. I know that it...
    deleted deleted 26-30 Jul 18

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    I am was involved with the mother of a friend of mine. It was a complicated relationship because she lost her son (my friend) and her husband to a drunk driver. I stayed friends...
    deleted deleted 26-30 1 Response Jul 12

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    I am now 71, and too old to do anything about this. But I have always longed to be a woman. To dress sexily like a woman can, to have sex like a woman, to teeter on tiptoe like a...
    peter13942 peter13942 70+, M 5 Responses Jun 29

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    My partner (female) wants another woman to join us. I took some convincing - believe it or not - and now I like the idea. We're both a lot of fun in and out of the bedroom so it...
    missinnyc missinnyc 31-35, M 2 Responses Jun 29

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    So, I'll be 18 in two weeks. Woohoo! I'm still afraid of the dark and I sleep my door locked and with my dog in the room. I have an aurora borealis night light that changes colors...
    XxSweetxSuffocationxX XxSweetxSuffocationxX 16-17, F Jul 1

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    I've actually never been in a relationship with a cross dresser, but I am seriously attracted to hot guys in women's clothing. Would like to understand more about the lifestyle and...
    danabug danabug 46-50, F 2 Responses Jul 2

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    Soldiers of Narnia are lurking on the other side. When the portal weakens at night, my sleeping soul stands guard to prevent humans from entering this magical dimension. (Just...
    Sourminds Sourminds 18-21, F Jul 7

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    I have a total of nine pillows. A huge pillow that sits against the wall, a body pillow, four pillows; two to sleep on, the other two for decoration but can be laid on, another...
    Samaccino Samaccino 16-17, F 1 Response a week ago

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    I really can't lol it's so uncomfortable to me and when I sleep my legs are usually all over the place lol so I rather just sleep in an oversized T-shirt or something Love...
    AshleyYoung98 AshleyYoung98 16-17, F 3 Responses 3 days ago

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    For eighteen years I slept with a stuffed animal and the only thing that broke that habit was finding someone to sleep next to
    Annapie Annapie 18-21, F 2 Responses Jul 3

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    Since I was about 14, I have been sleeping naked even when it's cold. I just love the feeling of feeling the duvet against my skin and being all wrapped up.
    Kinkycharlotte Kinkycharlotte 18-21, F 42 Responses Jul 7

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    It's actually more comfortable when you sleep bottomless🙈 Lol
    chasehux chasehux 13-15, M 6 Responses Jul 7

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