Masturbation Vacations (L/F)

This story contains strong language (L) and involves fantasy (F).
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My wife is a professional in her late thirties—highly educated, hard-working, and a wonderful mother. She is a pretty brunette with womanly curves. She has fabulous breasts with large, sensitive areolae and keeps her pussy completely shaved because she loves the way it looks and feels when she or I play with it. Oh, and one more thing: she is highly orgasmic.

We have a satisfying sex life, and to the best of my knowledge, she masturbates only once or twice a week. From what I can tell, she usually masturbates with her trusty Magic Wand, which she says always produces a quick and intense orgasm. But there are times that she lets it all hang out. Every two to three months, she will go on a little overnight masturbation vacation. Business will take her into the city, so she’ll stay at a downtown hotel and have an opportunity to completely relax without any chance of interruption from me or the kids. I believe she deserves the break from her daily busy life, so I encourage her to take this little break. She has told me that it is a great place to relax and be as uninhibited as she wants.

That’s where she currently is as I write this. My wife has incredible orgasms while masturbating, and I am often curious why she does not masturbate more often. On this current “vacation,” I notice that—besides her Magic Wand—she has taken with her two of her large dildos, as she likes one for her mouth and one for her pussy when she masturbates. One dildo is approximately seven inches in circumference with about eight inches of insertable length. The other model measures seven and a half inches around and has an insertable length of over nine inches with a very large, pronounced cock head. She says she rarely ever uses this one for penetration, though she says she likes the idea that it is there in case she gets extra horny and wants to try and fuck something huge. Both of the toys are exact replicas of extremely large cocks.

She has moved up her dildos’ size over the years as she loves the sight and feel of a large vibrating cock inside her. She says she loves the feeling of the dildos large cockhead stretching her vaginal lips as it enters her. I have seen her orgasm almost instantly after only two inches of one of her large dildos has begun to enter her. It is amazing to see her still-tight vagina accommodate almost the entire length of one of her bigger dildos.

She does not like to talk much about her masturbation escapades, as she believes a lady does not disclose such things. Over the years, she has given me just enough information to re-create what a typical overnight for her is like. She arrives at the hotel and gets comfortable in her room. Then she takes her toys (she like to call them “The Boys”) out of her suitcase and plugs in her Magic Wand next to the bed. She changes into a satin slip that gives her easy access to her breasts and beautiful pussy—of course, she wears no panties. Sometimes, she warms up with her Magic Wand to get her pussy nice and lubricated as she says the more orgasms she has, the wetter she gets.

After a few orgasms, her pussy starts to ache for penetration. She takes her incredibly realistic dildo and slowly slips it in her mouth to get it nice and wet. She says she likes to pretend it is a real cock that she is giving head to, and she is getting it hard and ready to fuck her sweet, tight pussy. Actually, she learned how to deep throat a penis by practicing on her dildos in this way. She swirls her tongue around its large bulbous head as her pussy instinctively gets wetter, knowing what is about to come. Then she removes the dildo from her mouth, and it glimmers with her saliva.

Spreading her legs wide, she puts the head of the large dildo at the entrance of her vagina. Before she slides it in, she uses the wetness of her pussy to coat the tip of the imitation cock, and then moves it up and down her swollen clitoris. At this point, her aching pussy cannot take it anymore. She lowers the head of the dildo to the opening of her pussy and begins to push. She says there is always some resistance with such a big cock, even though she has had masturbatory intercourse with its mighty form many, many times before.

She starts to orgasm quickly after the cock has begun to penetrate her increasingly wet pussy. As she continues to take the dildo inch by inch, it stretches her inner folds to the max. After she feels the head of the dildo tuck just past her cervix at the deepest reaches of her pussy, she starts a slow, rhythmic fucking motion with the dildo and quickly starts to orgasm again. She loves to watch in the mirror and see how much of the huge realistic cock she can take. At this point, there is usually an inch or less of the shaft left outside of her pussy. Then, she says, she likes to get into a realistic fucking motion with the dildo. At this point, she also likes to raise one of her breasts to her mouth and suck on her nipple in rhythm to her fucking. She will also sometimes take her other dildo into her mouth, playing that she is pleasing two big cocks. Both of these techniques intensify her orgasms. She has said that she will masturbate in this fashion for up to an hour before she is exhausted and spent from orgasms.

She has told me that, after her first masturbation session, she will drift off to sleep—sometimes with her dildo still nestled inside of her. She says there have been times that she has woken up with the dildo still inside her throbbing pussy and has started to fuck “him” again as she is waking up and starting the whole process over again.

She describes times that she removes her dildo after she fucks it and puts it on the pillow next to her. When she wakes up, she sees her substitute lover lying on the pillow, and it turns her on so much that she just has to fuck “him” again.

She says that she usually has about four or five “rounds” with her toys in a 24 hour period and countless orgasms. She then leaves for home, extremely sexually satisfied.

This is what makes her happy, and in turn, it makes me happy.

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17 replies
    • HornDog says:

      That's the point. I'm not complaining. I get so hard thinking about my sweet wife taking dildos in her wet pussy all night in some random motel.

    • HornDog says:

      The boys come out to play with wifey in case I can't keep up sometimes after a hot sex session. She craves *more* sex immediately after a good fuck. And I get hard immediately watching her taking on "the boys".

    • PacMan says:

      OMG! Learning2Wait is BACK!! That’s great news!! You are one of the all-time great contributors. ? Can you share a life update here? Still single? Any more visits to your mentor’s house?

    • HappyHubby says:

      I share Pacman's enthusiasm at your return. Welcome back! And an update would be wonderful. Last time you checked in you were engaged to be married. UPDATE?!

  1. SamtheMan says:

    I've been counseling for 20+ yrs and I'm not looking to benefit from this but just trying to provide insight. There a couple of comments that caught my attention. "My wife is a professional in her late thirties—highly educated . Yellow flag. I've counseled just under a hundred women over the years and the pattern of concern has been "professional" and "highly educated". You also said, "to the best of my knowledge, she masturbates only once or twice a week" So why is she masturbating? My wife of 40 yrs would never consider masturbating because she's satisfied by her husband when she has the desire. It's a good story telling about how she places the dildo between her legs but I'm hoping "praying" this is only once a year activity and that she is getting the pleasure she needs to satisfy her at home. Keep up your encouraging her but I'm sensing she may have the more sexual drive and is looking for more. Just intending to encourage where I see a lack of meeting the needs at home..

    • CrazyHappyLoved says:

      But sometimes a woman just enjoys pleasuring herself on top of the satisfaction she receives from her husband. And some husbands enjoy (or would enjoy) knowing that their wife pleasures herself just as he sometimes pleasures himself, neither denying the other any sexual satisfaction they want from each other. I guess that couples for whom these activities are normal, happy occurrences wouldn't end up in a counselor's office. For those who do, I expect that you teach them how to better communicate their needs and be sensitive to the needs of their partner, right? If either spouse has a higher drive than their partner, being able to use masturbation as a tool to handle that drive seems to be much more helpful than keeping it bottled until someone makes a move on them. And if that self-pleasure also turns on and brings pleasure to the lower-drive spouse, all the better.

    • SouthernHeat says:

      I am a very happily married to the love of my life for 33 years. I’m higher drive, and in the early years, I did not masturbate. It put more pressure on him and caused tension and bickering in our marriage. I got over the guilt I had been taught about masturbation, and I learned more about my body, and it became easier to orgasm. That helped my husband, so sex was more enjoyable for both of us. My masturbating relieves frustration and makes him feel less pressure to perform. He loves that I do it, and he loves to watch me at times. It’s strengthened our marriage because we are open and have good communication.

  2. Tango69 says:

    The next gift giving event, maybe consider buying her a we-vibe. They are pleasure for you and her. I masturbate and love my magic wand too. Invite it into you encounters with her or maybe you can be the driver of it. I find it hot and want to throw mine across the room to get my husband's cock in me to replace it during times I bring it to our sessions. I’m not saying you should change a thing, just a suggestion as you would really benefit from both together, I feel.

  3. Salcpl says:

    It is so stimulating to see your wife enjoying herself. I enjoyed your story very much. Care to share the brand of her dildos? I want to find the most realistic dildo possible for my wife. We have tried several that just didn’t feel real enough.

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