Helping A Lonely Older Man



What’s your gender? Woman
How old are you? 25
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
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Nursing Resident
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Sharing your body with someone is an intimate expression, but it doesn’t have to be affectionate or romantic, it really is ok if it’s “just sex”
How many sexual partners have you had in your life (including oral sex)? 18
How many hookup stories have you here posted before? None

Helping A Lonely Older Man

How long ago did this hookup happen? I was 19 at the time

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand, Therapeutic (for my partner)

How long did you know the person before this hookup? For more than 3 years

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? Robert had been my family’s next door neighbor for years. He was white, in his late forties but didn’t look a day over 30, very easy on the eyes. He was an ex-marine, 5’9” and well muscled. He’d packed on a few extra pounds, but he wasn’t fat. All in all, a very sweet man.

For comparison I’m blonde, about 5’6” and lean, very tan, C-cup tits, firm round ass.

His wife had passed away about four years earlier and he had turned into somewhat of a recluse, very lonely and depressed. The only time I would see him outside of his house was when I would help him keep his late wife’s flower garden maintained. I would also help him out around the house and just keep him company. My parents encouraged this since Robert had been such a good neighbor for so many years, and I liked him anyway and felt like he needed a friend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He often made lunch for me when I was over, and he was a really good cook. One day when we were talking over lunch and he brought up how lonely he was. I asked him if he had thought about putting himself back out there and hitting the dating scene again. He said he had but then shook his head and said that he’d been out of the game for a long time and wasn’t the man he used to be. I flat out told him that he was still a good man nonetheless and it sounded like he just needed to get his mojo back. He kind of chuckled and said that it was probably true, but he just didn’t know how to get back out there and look for love again. I chuckled and said he was getting ahead of himself, and that he didn’t need to go out and find love again straight away. I told him that first, he just needed to go out there and get some pussy. He laughed so hard that he spit out his drink across the table, saying he hadn’t expected that from me. I was trying not to choke on my food because I was laughing too. I managed a smile and eventually said that it was the truth. I took away two things from this, that his confidence was very low, and that he was afraid of being rejected. At this point I hadn’t been planning to hook up with him, I hadn’t even considered that, but I did want to help him somehow.

That weekend I was helping him sort through a bunch of boxes that were packed away in the closet of his spare bedroom. Yes, bedroom probably sounds convenient I know, but hey. It was what it was. Anyway, I asked him if he had thought any more about trying to date again and he said he had, but he just wasn’t sure how to get to know a new woman. I suggested maybe getting closer to a woman he already knew that he found attractive. He laughed and asked if I was talking about my mom because he didn’t think my father would be to keen on that. I was stunned and flung an empty box at him, joking and asking if he was nuts. We had a decent laugh over that. He continued, saying that most of the women he already knew were either married or were a couple of decades older than him. I smiled and joked that the older ladies needed some love too. He jokingly retorted that I had said a woman he was attracted to. I jokingly said he was terrible.

Later on, as we were finishing up with the boxes in the spare room, he idly mentioned that I look a lot like my mother. It suddenly struck me that he had been trying to hint that I was a woman he already knew and that he was attracted to, but was avoiding being direct about it. I was stunned at how hot I found that. I quickly confronted him with my realization and it didn’t take much pressure for him to cave. He seemed a bit ashamed, but I smiled at him and mentioned I’d caught him checking me out really hard multiple times in the past. I asked him straight up if he had fantasized about fucking me. He was more hesitant with that, but I pressed him and he admitted that he’d been wanting to fuck me for a while. He honestly didn’t think a young woman like me would be interested in him. I told him that was nonsense and that I thought he should fuck me, reminding him that I was the one who suggested he needed to get some pussy. He seemed uncertain, so I added that I was willing and we both knew it would be good for him. My mind was made up and I felt good knowing how I could help him.

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? I ultimately had to take matters into my own hands and started undoing his pants, he didn’t try to stop me. When I got to his cock I was pleasantly surprised, he was already rock hard and although not much over 6 inches, his girth was impressive. I had never seen such a thick cock. I started giving him a blowjob and that seemed to loosen him up as he put his hands on my head and started thrusting into my mouth lightly as I sucked him. I got up and started to undress and he did the same. I got on the bed and told him to eat me out, which he did with an expertise I’d never experienced before. I moaned louder than I ever had when having a guy eat my pussy and I’m pretty sure my nails made his scalp bleed. I orgasmed nice and hard and then he moved up my body licking and kissing while I arched at his touch. He pushed my legs back and I stared at his cock as he lined it up with my pussy. It was a beautiful cock and I couldn’t wait to have it inside of me. I gasped as he started pressing it in and told him I had never had one so thick. He reassured me that he’d be gentle, and he was very gentle, easing it into me a little at a time. I was gasping and moaning with every inch until it was all in and I couldn’t believe how incredible it felt. He put his fists into the bed on either side of me and started thrusting very slowly and gently.

As my pussy loosened for him he began to thrust deeper and more aggressively, I grasped his arms tightly, gasping. He slowed a bit and asked if he was hurting me, and I told him that it felt amazing. I told him to take me good and hard and that I’d let him know if it hurt. That spurred him to fuck me the way I knew he needed to, like a lonely man who hadn’t had pussy in years. I dug my nails into his arms as he pounded me like a rutting bull and he was grunting like a wild animal which I found very hot. He had incredible stamina and took me like that intermittently for close to 30 minutes, and during that time I had two very powerful orgasms and though he slowed on occasion he never stopped. He pulled out and told me to get on all fours and then he took me from behind. He said he hadn’t had a pussy this tight since high school and then smacked my ass which I loved. He held my hips and started pulling them back when he thrust forward, grunting as he enjoyed my pussy. He slowed a bit and asked if he could cum in me since he wasn’t wearing a condom. I laughed and said I had figured that was the plan all along. He went back to fucking me very roughly, his grunts soon becoming more urgent, his thrusts more shallow. I heard him gasp as he pushed in deep and then he started moaning loudly and I could feel that beautiful thick cock spasming inside me followed by spurts of warmth. He thrust in and out roughly a few times as he came. He pulled out and we both collapsed on the bed, sweaty and completely spent.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I felt amazing about it the next day, despite being very sore. We didn’t talk about what had happened until several weeks later, but he seemed like a much happier man. I was very happy to hear that he was seeing someone, and he told me I had been right about what he’d needed. I told him I was glad to have helped and asked if he had any feelings he wanted to express about what we’d done. He told me that he couldn’t express with words how much he enjoyed actually getting to fuck me as he’d fantasized about, but now he was uncertain how he should feel about it.

I assured him that he shouldn’t be ashamed of it. I reminded him that I had offered myself to him and he should feel good about that, given that he’d been convinced I wouldn’t have been interested. That seemed to help a good bit and he thanked me for making him feel like a young man again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel better about myself, Didn’t want to disappoint my partner, I knew it would be good for him

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? I don’t know / I’m not sure

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

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? We didn’t tell anyone because if my parents had found out it would’ve been a very bad thing for both of us, but especially for him.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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

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? I felt good that I was able to use my body to help a friend and make them feel better about themselves. I also got to experience the talents of an older man with decades of sexual experience, not to mentioned that beautiful thick cock.

What was the WORST thing about this hookup? I was very sore for a few days, but it was worth it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? In this case, for me, it was more about what I was able to give my partner by letting him enjoy my body and it turned out to be a very good thing for him. I feel very good about that.

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? There is absolutely nothing wrong with an older man being attracted to and wanting fuck a much younger woman. So long as the woman is not a minor and gives consent I feel this is perfectly natural.

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? Casual sex is a very natural thing, and as long as you are comfortable it can be a very healthy thing to engage in.

What do you think about the Casual Sex Project? I like that it shows how all types of people have sex with each other for all types of reasons.

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