A few years ago I was a young private in the U.S. Army. I was stationed in Fairbanks Alaska at Fort Wainwright with the 25th infantry. I was an extremely horny and inexperienced boy and only 18 years old. One summer weekend I was horny and browsing the craigslist personals ads and saw a woman in her late fifties offering “full service” massages for $50. I messaged her and asked if I could come by. She said yes and gave me the address.
It was almost 40 minutes out of town and it was a small cabin/house out in a small plot of land.
I was extremely nervous walking up to the door. She asked me to enter through the back in our messages because she lived with another woman and didn’t want to bother her.
When she answered the door and let me in I got to actually see her. She was extremely overweight but not so big that she couldn’t walk normally. She had long salt and pepper hair and an absolutely enormous set of tits. They were the main thing that I noticed. She looked like shed have to get her bras custom made.
Her little house was very cluttered with cat trees and boxes of stuff and there were at least 5 cats running around. She motioned me to a pull-out couch and told me to undress.
I layed down on the couch and she sat next to me and oiled up my entire body and began to massage my back. I asked her if she could take her shirt off and she obliged. She gave an amazing massage and even focused heavily on my hands and my ass which I really liked. The entire time her massive, but saggy tits were rubbing all over my back and it kept me rock hard the whole time. After about 30 minutes she had me roll over onto my back. She began to focus a lot on my crotch without actually touching my cock. She let her tits rub over it though and that was the first moment that another person had touched my cock.
She kept rubbing me for a while and then asked if I wanted to cum. I sheepishly said that I did. She then asked me if I wanted a hand job or a blow job. Again, I nervously told her that I wanted a blow job. She didnt wait. She slid down to my cock and started to blow me. It felt so new and amazing but it was hard to enjoy fully because I felt so awkward. After a couple of minutes though, I began to get into it. I started moaning and thrusting up into her mouth and I think that kind of got her into it a little more. She began to blow me with a little more enthusiasm and even started to deepthroat me. It was a pretty clean blowjob at first, but now she was beginning to drool and spit onto my cock. This only made me moan more and thrust into her throat harder.
This went on for about 10 minutes I think but at some point she stopped for a second and just looked at me. I thought something was wrong at first, but she just got up and came to sit next to me. She started jacking me off with all of her saliva and leaned in to kiss me. I kissed her back, deeply. Her tits felt so soft against my chest and her tongue was licking all over the inside of my mouth. She reached her hand down into the crack of my ass and started rubbing my asshole. I wasnt really into it but I didnt say anything. She took her other hand and started to jack me off again while she slowly worked her finger into my asshole. This combined with her tongue working it’s way into the back of my throat and her spit running into my mouth had me completely overwhelmed. The sloppiness and messiness of it all is what really pushed me over the edge. There was so much of her spit on my cock, between my ass, and in my mouth. It was something that I didnt know I liked up to that point but I found it extremely hot.
She could tell that I was about to cum and she began to ramp everything up. She jacked me off harder, she pushed her finger deeper into my ass and was rubbing my spit covered balls. She kissed me deeper and even more sloppily. It was so messy and so overwhelming but I just gave myself to her. She was this big older woman taking control of me, a young and athletic soldier, and I loved it. She made me feel like I was her little bitch. I was just laying there on my back with my legs up in missionary position while she did whatever she pleased with me.
She was fully finger fucking my ass and stroking me hard by this point and I just couldn’t last any longer. I came a massive amount and shot all over my chest and onto her tits. I was moaning into her mouth as I came and we never broke our kiss. She pulled her finger out of my ass, but she kept on gently stroking my cock as it went limp. We continued to lay in that position for a couple of minutes, just kissing while she rubbed her hands up my chest and into my cum, then back down onto my limp cock and into the crack of my ass. As she sat over me she was still sloppily kissing me, spitting into my mouth, but now she was giggling a little bit at me as she rubbed my cum and her spit all over me. It felt so good to just let her slide our mess all over my body, especially when she would run her hands back down over my asshole. The entire time the kissing never stopped. I loved it.
After a couple of minutes of this though, that feeling shifted to one of shame and awkwardness. I quickly got up and put my clothes on without cleaning myself off. I rudely tossed her $70, which I felt bad about and left without saying anything.
It was an incredibly formative experience that I have learned to think back on fondly. Because of it I have a deep passion for older women that somewhat fit her body type. I love that sloppy and spit filled kissing we did and I kind of have an oral fixation.
If I could go back and see her again I’d do it in a heartbeat.
Source: reddit.com/r/gonewildstories/comments/mskl76/mf_my_first_sexual_experience_was_with_a_woman