The Tender-Hearted Wolf



What’s your gender? Woman
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA – California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Getting divorced three years after husband’s brain injury. Was married for 18 years. It’s like he died three years ago.
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? High sex drive but pretty frustrated at the moment.
How many sexual partners have you had in your life (including oral sex)? 10’ish
How many hookup stories have you here posted before? 1

The Tender-Hearted Wolf

How long ago did this hookup happen? 4 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Barry — his name obviously wasn’t really Barry but when I first met him he told me his name was “Ben” which was also a crock of shit and I figured that out fairly fast. I thought I knew what his real name was but for some reason his looks struck me as a “Barry.” So I only ever called him Barry. Barry-meister. Barry man. Barry. It fit him well and he loved it that I renamed him. He’ll always be Barry to me. I just loved calling him that. He had dark hair. Stocky build. Mildly hairy chest, as he put it which was more than true. It wasn’t super hairy, but hairier than I was used to and I thought he looked great. He was a few years older than me at 55, but he had a baby face. He looked much younger. He was handsome from the side, but when he smiled his side teeth were spaced slightly too far apart and he had an odd horsey face from the front. Still, I had wild amounts of fun just hanging out with him and his ease and the way he constantly told me how me he loved my body just immediately put me at ease. I could have hung with Barry every day forever and been happy as a clam. He did this thing when we were walking down the street. He’d offer me his arm and I would cuddle up close and we would walk and talk and it was great. But I didn’t love Barry and eventually that did our tryst in. I wasn’t getting back nearly enough to make it worth my while. We met over Ashley Madison while I was trying to figure out what to do with the first man I slept with after my 18-year marriage came crashing down after my husband’s brain injury. The first man, “V” about whom I wrote a story this morning which will hopefully be posted soon, was unbelievably wonderful but kept me at a great distance while demanding the world of my emotions. I was confused, extremely frustrated and wanted something, anything, different than V. So while I was still fostering some kind of connection with V, who was the true target of all my emotions, I met Barry and started a romance with him too. I never slept with Barry at the same time I was fucking V, but I did blow Barry in my car one afternoon at the dog park before V and I had completely called it quits. I felt secretly empowered by that! Two men at once! Who would have ever thought I would be capable of that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Barry and I were fairly short lived, but he was fun loving and carefree and we met frequently for coffee or lunch — particularly in January 2016 while he was briefly unemployed. I had so much fun in January … on this particular occasion Barry and I had already slept together once in early December 2015. The next time would not be for over 6 weeks and it was a long, dry spell for me. I was ending a marriage, packing up a huge house, getting kids used to the idea of moving and leaving their father, and trying to sell the house. Things in my life were in chaos, but Barry always made me feel better.

We arranged for him to come to my house in the middle of the day. Barry is a simple guy. He lives in a one-bedroom apartment in a very hip and cool neighborhood not far from my old house with his much older wife. He did not have children, and despised the thought of any children, but loved hearing my stories of my kids and their sports and our lives. He was very good at getting me to talk and putting me at ease. And unlike my desperate efforts to get V’s attention, Barry never had to be told even once to compliment me, or tell me how good my body looked and tasted. He was forever sending text messages telling me what he was thinking and what he wanted to do to me.

Because both of us were facing money issues, we decided to come to my house and skip the cost of a hotel.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? So mid-January 2016. He came over around 11. I gave him our address and he showed up on his motorcycle right on time and parked around the corner so neighbors wouldn’t notice. He came into the house and my two dogs immediately wanted to eat him alive. I gave them giant bones that I had purchased at the butcher shop just that morning which occupied them for the next several hours and let us go upstairs to have some quiet time alone. My husband was gone all day and the kids wouldn’t be home from school until 3:30. Barry first started kissing me in our kitchen. It was a bit weird to have him in my house. He is a good size, not much taller – maybe a couple few inches — than me at 5’7″ but he was big and his arms felt really strong around me. He started running his hands up and down my back and ass as he kissed me and the kissing got more frantic. We then went upstairs to my bedroom and he threw me down on our large king sized bed. The room was light and bright since it was still morning. The views out toward the ocean from my bedroom were clear, and it felt like we were on top of the world. He took my clothes off except my panties, and laid me down on the bed on my back and kissed down my stomach until he got to my pussy. He gently bit my pussy through my underwear and took a good long sniff of my smell before even taking off my panties and throwing them to the side. Once the panties were off Barry let out a sigh of approval. He insisted that I let my armpit hair and pussy hair grow long. I have Slavic blood and lots of dark thick hair. I usually clip and trim my pussy hair but not with Barry. He wanted it as wild and untamed as possible. He started licking and kissing my pussy all over, with his face deep inside me. He tongue fucked me which made me moan louder and louder. He alternated between steady strokes over my clit with his tongue and sucking my clit as I got closer to coming. Finally with one suck I just felt the orgasm wash over me and I let out a loud gasp and moan and wrapped my legs tight around his head. He kept licking and sucking me for a while before taking off his boxers. I brought him up to my face and gave him a long, hard kiss to thank him for such a nice orgasm and to taste my juices on his mouth. Barry’s cock had this amazing ability to grow. It doesn’t look particularly big but when I would suck him and lick him, it would get larger and larger in my mouth until suddenly I was choking a little. I tried to put all of him in my mouth, and he commented about how great it was that I could get him all the way in. It was unusual for me that I loved sucking Barry’s cock so much. With my husband I never really wanted to give him oral sex much. It just wasn’t enjoyable which I think had more to do with psychological reasons (he faced addictions and I was angry and felt abandoned by him). Barry just loved my body and I felt no qualms about going down on him and really focusing on his beautiful cock. It tasted good and I loved knowing that he was getting so much pleasure from me.

Barry liked the feeling of a tight pussy and he maneuvered my legs around to the side so he could enter me with the pressure of my legs closed around his cock. He could plunge deeper inside me that way, even if it hurt my hips a bit to be pushed and pressed around like that. But I loved the feeling of his body weight on top of me while his cock was pounding away inside of me. He kept commenting on how much he loved my “sex face” and how different I looked while getting fucked. Unlike V who was entirely quiet, Barry talked a lot during sex and let out a loud scream when he came. I have never heard anything like it and I was a little concerned about what the neighbors must have thought. But Barry really did scream out loud as he was coming. A high pitched piercing scream. So funny, but sexy too once I got over the initial shock of hearing it.

The problem with Barry was that he was fucking other women. At least two others when we first started seeing each other last year, and by the end which was this past March only one other woman besides his wife with whom he was no longer having sex. I tried hard to be ok with Barry’s womanizing. The health concerns bothered me a bit. I had tested clean, which I expected after basically only a handful of partners in my life and having been monogamous over a 24-year relationship with my husband. But I wasn’t so sure about Barry. He did get tested for me in the midst of our several hookups, and that was nice and I really appreciated it. But it wasn’t full protection. We did not use condoms during sex because at 55 he had a hard time staying hard unless we went bareback. I was ok with it but uncomfortable. Going forward I will have to insist on condoms and I’m waiting to get tested again just to make sure I’m ok.

I used to tease Barry that he was a “tender-hearted wolf” because he had all these women and was clearly manipulating all of us. But he was up front and honest. He really did want an emotional connection with the women he fucked. And he didn’t want anyone mad at him. I called him a wolf once, to which he laughed out loud that anyone would ever call him that. So I said “fine, but you’re a tender-hearted wolf nonetheless.” And it stuck. He also pointed out that I should be ok with his womanizing because I had “Barry” all to myself and shouldn’t worry about it. I worried about it. It bothered me and I couldn’t do it anymore at some point.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Barry took a shower and looked so cute in a towel hanging around my bathroom. We split a sandwich in my kitchen, he gave me a long slow kiss and he skipped down the front steps and up the hill back to his motorcycle to leave.

By February this year Barry was back working and I never saw him. We only hooked up a total of 3 times. I faced the same problem with Barry that I had experienced with V. No time for me. My needs were never met. There was little to no sex, none when I really needed it, and I was expected with Barry to share even less of him with other women. One afternoon in March while we were grabbing coffee because I was exploding and just needed to see him to talk about my move and divorce and all that was happening in life, he said something about the other woman he was fucking. That was it. A light switch flipped in my heart and I realized I didn’t want that. I didn’t need to be reminded that I wasn’t really all that important after all. I guess I need a relationship and casual sex isn’t for me. I don’t seem to have much of a track record with it. At least not happy endings.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To cheer myself up

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I didn’t tell anyone about the specific hook up, but I have disclosed to friends and family that I have been dating again. Given my situation at home with a husband who basically died and became a vastly different, very unpleasant person, no one judged me for dating again. All of these experiences I have had this past year have helped me move on in life from a long-term relationship with my husband and from the grief of losing him. My husband and I — even though we are divorcing and even though he is physically and cognitively compromised — have been getting along better than ever. I get to move on in life and find what I need. He is happier living on his own. We will always be in each other’s lives, just not as a married couple. Casual sex, at least the way I have it, has helped me get to that point.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Barry’s appreciation of my body and how at ease he made me feel with him and myself.

What was the WORST thing about this hookup? That Barry was fucking other women and really didn’t need me as much as I wanted him to want me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex is great. Not one night stands. That’s not what I want. I want someone who like me doesn’t have time for a full blown relationship, but who needs sex regularly and enjoys an emotional component to the relationship as well. I don’t know what I want. But I have had fun figuring it out even if I get a little too attached. I have to learn to stop doing that, but still have fun with the men I’m meeting.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Barry is a good guy. We aren’t talking at all now and that makes me sad. But I can’t hang around hoping that he’ll have a scrap of time for me. It just didn’t work. I could have even dealt with the idea of the other woman if had been getting more attention. Sex once every 6 weeks didn’t cut it for me.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It has helped me move on from my husband, feel good about myself, and feel like a sexy woman again after dealing with the spouse’s severe illness in the past 3 years. I never thought that in my 50’s I’d be having an interesting sex life again. I need to work out the kinks and find someone right for me, but it has been really great. Despite feeling lonely and frustrated. I know there is someone out there for me.

What do you think about the Casual Sex Project? It’s fun. I read all the stories.

You have a hookup story to share? Submit it here!