My [M] night with the older family friend [F]

For many years, my family would go to a Christmas party at Melanie’s winter cabin. Melanie lived in our neighborhood and had similar aged kids as my siblings and I, and my mom became very friendly with her as the years passed, so much so that we even attended her annual Christmas party at her winter cabin that was only about 45 minute away from our neighborhood. The parties were always a blast growing up, lots of kids running around and the parents all having a good time.

As the years passed, Melanie separated from her husband, and us kids all went off to college. I stopped attending the annual party once I turned 18. My mother and Melanie’s friendship became strained (I think it was related to fallout from Melanie and her ex-husbands divorce) and my parents also stopped attending the party.

For background – Melanie was always very welcoming and friendly to everyone. She wasn’t knockout gorgeous but as I hit my teen years I began to take more notice of her. She had dirty blonde shoulder-length hair and green eyes. As I got older I began to appreciate her soft looking full lips and her big breasts. She dressed modestly but It was clear to see she had a nice big rack every time she wore a sweater that hugged her chest well. I recall she was always concerned about her weight and trying different diets/workouts, but to me she seemed naturally sexy. I would fantasize about her but of course never thought anything would ever come of it.

Flash forward to last year. I am 23 and living at home after graduating college. Melanie is divorced and also no longer friendly with my parents and its been years since any of us attended her party. I was at the local bar where people would always go to on the night before Thanksgiving. I was with my friends and we were all having a really good time. My girlfriend from college had dumped me a few months prior and it was my first time being single in a long while. I am tall, handsome, and in great shape, so I had my options when it came to dating and hooking up, but I was in a bit of a rut after my breakup and also, I am not the most confident and outgoing person.

It was my turn to buy a round so I was waiting my turn to order at the crowded bar when I see Melanie a few people over, also waiting to order. We make eye contact and smile and I shuffle over to hug her and say hi. Although her and my parents had a falling out, I still thought highlight of Melanie and it was clear she didn’t hold anything against me.

It had been years since we had seen each other so she commented on how grown and handsome I looked. I probably blushed hearing that as I smiled and thanked her for saying so and told her she looked awesome and that I was happy to see her. She thanked me for the compliment but made a self-depricating comment about having put on extra weight. I honestly thought she looked fantastic and sexy as ever, and I think she felt this way about herself because her ex-husband was now dating a younger and very fit women.

We chatted for a few more minutes before finally both getting our drinks, and before we went our separate ways she told me that I should make an appearance at her Christmas party this year – I guess the winter cabin stayed with her through the divorce. I told her I would have to take a look at my schedule to see if I had anything going on that night, so she gave me her number to put in my phone so I could let her know if I would be attending.

I wasn’t planning on going to the party. I didn’t know who was going to be there and I was more interested in finding a party or bar to go to with my friends. As the night of her Melanie’s party arrived, my plans had fallen through. I had a couple beers by myself and decided to text Melanie to see if I could still come. She texted back saying that a bunch of people had backed out because of COVID, but that the party was still on and that she would love if I made an appearance.

I hopped in the shower and changed and began making my way to the party. I arrived at the cabin around 8:30 and there were only 3 cars parked outside. I immediately regretted my decision to come, but I had driven 45 minutes, so I figured I should at least pop in for a drink and to make an appearance. I walked in the cabin and saw 6 people sitting around the dining table drinking and playing a card game. Melanie got up and walked into the kitchen to greet me. I handed her a bottle of wine as a gift and she gave me a big hug.

She was wearing a red crushed velvet blouse and had just enough buttons undone to reveal a bit of cleavage. Her bountiful chest was snug up against mine as we hugged. I ran my fingers across her soft velvet blouse as I pulled away from the hug. I wanted so badly to rip the other buttons apart and to reveal her big tits. I snapped back to reality and joined the group at the table and started drinking and playing card games with them. After about an hour of my arrival the other handful of folks at the party started to leave. Once the first couple people left the others followed just after, leaving only me and Melanie.

I felt a bit awkward at this point so I told her I would finish my drink and get out of her hair. She apologized for the small showing at her party and said I was welcome to stay for a couple more drinks since the night was young. I decided to stay and she made us some cocktails and she suggested we make our way into her living room to get in some more comfortable seats. We sit down on a love seat and start catching up with each other. It had been so long we went without seeing each other there was a lot to catch up on. She made us a few more cocktails as the time passed.

She eventually opened up a bit about her divorce and she eventually asked me about my love life. I told her about my ex and our relationship and how I was finally getting over the breakup, but that I was having a hard time adjusting to being single. She laughed at me and said she just would not believe that I had any trouble at all with girls. I went on to explain that my biggest hurdle was being confident and trying to be more outgoing in my pursuit women.

She said she had some advice for me and told me that in life, sometimes if you want something, you just have to go for it, or else it will never happen. At this point she offered to make us another drink. I sat on the love seat thinking about her advice. I was unsure if she was directing that advice about us in that moment, or in general. My heart was pumping and I decided in that moment that I should at least try making a move on her.

She sat back down next to me and handed me another drink. I took a few sips as I tried to plan my move. I glanced down at her cleavage and asked if I could touch her blouse because it felt so soft when I had hugged her when I arrived. She had a surprised look on her face and started laughing. I felt very stupid and started to apologize but she stopped me and said no it’s fine, and she grabbed my wrist and guided my hand over her shoulder. She looked at me and said “that feels nice doesn’t it”?

I leaned across and moved in to kiss her. She met my lips and we had a quick sensual kiss for about 5 seconds before she pulled away. She put her drink down and told me that she “can’t do this”. I apologized for putting her in that position and told her that I was just taking her advice. “I wanted you….so I went for it.” She looked me in the eye for a few seconds before leaning back in to kiss me. She was such a good kisser with her big fluffy lips.

She leaned back on the couch and pulled me on top of her as we made out. She reached her hands down my pants and slid the under my briefs and grabbed my ass cheeks. I started dry humping her as my cock was bulging against my jeans as I was fondling her tits over her blouse. I slowly unbuttoned three more of her buttons and pulled her huge right tit out and started kissing all over, before focusing on her big hard nipple. At this point she suggests we relocate to her bedroom.

We continue making out as we slowly make our way to her room. She flicks on a lamp and guides me over to her bed, which is king size with a large faux fur comforter spread out. I tell her how cozy her room is and she knelt down as I stand over her and started removing my belt and pulled my jeans off. As I stand over her in my briefs she runs her hands up my thighs, 6 pack, chest, and down my arms. She then slowly pulled my briefs down to reveal my hard cock. She grabbed my cock with her left hand and tapped it against her big lips. I let out a moan as she slowly suctions my tip with her lips and circles her tongue around my head. She teases me for another few seconds before standing up and telling me to get comfy on her bed as she walked into her bathroom.

I plopped right onto her big bed and lay on the soft faux fur – it felt like a cloud against my naked body. After a couple minutes of waiting, Melanie walks out of the bathroom in a sexy black bra and thong set. She asks if she can turn the lights down cause she’s self-conscious. I told her she looks amazing but that she should do whatever makes her feel comfortable. She turned the light off and crawled onto the bed and slowly on top of me. She propped a couple pillows behind my head and told me to relax.

She began making her way back down the bed, stopping to kiss my lips, then stomach and thighs as I lay flat on my back with my throbbing cock flipped back against my stomach. She positions herself between my legs and starts licking my big ball sack. I close my eyes and just lay there as she began taking my shaft into her mouth. As she hears my heavy breathing and light moaning she gets more into it. I start gentling thrusting into her mouth and she guides my hands on her head as she gargles on my cock. She starts moaning as I thrust a little harder. My hands stay on her head as she aggressively deep-throats my cock. As I felt myself close to cumming I let her know that I needed a second or I was going to cum. She pulls her mouth off my cock as her spit flows down my shaft and tells me she wants me to explode in her mouth.

I lay back and close my eyes as she sucks on my balls and jerks my cock. She starts deep throating me again and I can hear how sloppy it sounds as I tense up and feel my release coming. She can sense I’m about to shoot my load and she takes me entire shaft in and sucks up every last drop from me.

She climbed back up next to me and we cuddle as we both regain our breath. I told her how magical her mouth felt and we start making out on the bed. She told me her ex never let her kiss him after going down on him and she loved that I didn’t have a problem with it. We share a sloppy kiss as I unhook her bra and toss it to the side of the bed. I leaned her flat on her back and straddled over her as I worshipped her big tits, switching between sucking on fondling her nipples. I flip back next to Melanie and suck on her right tit as I reach my hand down her thong and rub her clit gently.

Her breathing picks up and I notice she buried her head in the pillow as I work around her clit and enter a finger inside her. Her pussy was already fairly wet but became much more so as I fingered her and played with her tits. She started aggressively kissing me as she started to cum and once she settled back down I told her I needed to taste her.

I slid down and removed her thong as I gently kissed her thick thighs and teased her about before I started sucking on her clit and sliding my finger inside of her. As things built up I pulled my finger out and slide my tongue in and swirled. I reached my hands up and grabbed her big tits as I continued eating her delicious pussy. Her stomach began tensing up as she thrust her hips against my face. I let her control the pace until she came again. She pulled my head off and guided me back next to her and we started making out again.

Not going to lie, it was hot making out with her after we had both gone down on each other. In the moment, it just felt so sexy. As we made out she felt my cock stiffen up again against her thigh. She reached down and started stroking me and whispered in my ear that she wants to feel me inside of her. I get on top of her and slowly slide my tip inside of her. She was very wet from all the foreplay, so after a few thrusts I was all the way inside of her. Feeling her wet pussy tighten up around my throbbing cock with each thrust drove me wild. Her big tits pressed up against my chest as I pumped, my heavy balls dragging across the soft faux fur with each motion.

She asked if she could get on top of me so I flipped onto my back as she climbed on top of me. Her huge tits hung down over my face as she slid down me. I let her control the pace at first as she slowly slid up and down, letting my throbbing cock press against her clit each time she thrusted. I was playing with her tits as she rode me. She had me so worked up riding me and it was time to take over a bit more control. I slowly moved my hands onto her ass cheeks and spread her ass a bit as she was riding me, allowing for a deeper angle. I felt cum all over my cock and I gradually started thrusting harder and smacking her ass cheek as she rode me.

She again buried her head deep in the pillow next to my head as she moaned and took my cock. I finally pulled out and asked her to lay flat on her stomach. I got on top of her from behind as she lay flat and started mounting her. I grabbed her chubby as ass cheeks as I fucked her. This was the deepest angle yet and I knew I was lose to summing again. I wrapped my hands under her to grab her tits from behind as I continued mounting her and as I felt my release coming I pulled out and came hard on her ass. After a while we got up and showered together. She suggested I spent the night since we had been drinking, so after we showered we laid back down naked. We fell asleep spooning with my cock resting against her chubby ass.

Source: reddit.com/r/gonewildstories/comments/you7ao/my_m_night_with_the_older_family_friend_f