At the time of this story I was in my early 20s in college and living out of my home state for the summer for an internship. I had struggled to find a place to stay but had happened upon Jackie’s place a few weeks before I was due to start. She seemed nice enough a mom with all her kids grown up and renting out their old rooms to make some extra money. I rested easy knowing I had secured a place to stay and could focus on my finals.
Upon getting there I went and knocked on the door and was greeted by Jackie. I never did find out what age she was but my guess was late 50’s although she looked like she was in her 40’s. She was about my height which is male average with brown eyes and dark brown curly hair. She was insanely fit for someone of her age and I would later find out she went to spin class almost daily. She had small breast, a rock solid ass and was dressed in a skirt showing off her legs. Myself I had let myself put on a few pounds but was still in decent shape and a summer of running would shave those off. I am average height, short blonde hair, and a 6.5in thick cock.
Jackie showed me around the place and where I would be staying. She then offered to go grab some food with me and we headed down a few blocks. She immediately started drinking when we got there and proceeded to tell me how a few months ago she had caught her husband cheating on her. She then explained that she was going out and extracting her revenge by hooking up with lots of men till the divorce went through. You would think this all would lead somewhere but we headed back to the house after a little more conversation/food and I got settled in.
After this I heard little bits of Jackie’s exploits but never a hint she saw me as anything other then a tenant. And truth be told I had a hard time not seeing her as a mom as I sat in her home surrounded by their family pictures. The summer went on and I started to go on some dates as I got to know people in the area.
One such date was with a girl named Amber. Amber was just a inch or so shorter then me, same age, and thick but not out of shape as she lifted weights regularly. She had straight black hair, tits that were probably a E cup, and a big well toned ass. She dressed sorta folksy as well which added to her charm and innocence. I really expected nothing but a few fun dates from the encounter and we went out to a casual restaurant on our first encounter. We had some great food and conversation and strolled the shops even exchanging a kiss here and there. Amber had to run to a family event afterward but it wasn’t long after she was texting me.
“That was fun, sorry we couldn’t keep hanging out today. I enjoyed that little move you pulled at the end too ;)” – A
I had made out with Amber a bit before she got in her car and cupped her ass at the end.
“I had a great time too! I hope I get to continue that, the next time we see each other ;)” – Me
“I would like that, I think we can do a lot better then that” – A
“What did you have in mind :)” – Me
About 10 minutes went by and picture of Amber’s tits popped up on my screen and a message.
“I think you can use your imagination ;)” – A
Since she had set the tone I happily sent a dick pic back to her.
“I certainly can” – Me
Things escalated from here and the sexting continued while we waited for an opening in our schedules a few nights from then. The night before we were scheduled to meet she sent me a picture of her getting changed in waxing salon. Finally the day had come and we arranged to meet up nearby the house where I was staying. We quickly decided to skip the fan fare and just head right to my room. Jackie wasn’t home so Amber and I had the place to ourselves and didn’t need to worry about noise.
Despite Amber’s initial persona I had found out from our sexting she was very experienced, quite a bit more so then myself. When we got to the room hands already all over each other she quickly stopped me pulling all her clothes off. Out of her bag she pulled out a blindfold and told me to put it on and wait. I climbed onto the bed with the blindfold on and tried to listen to what she was doing. A few minutes later Amber instructed me to remove all of my clothes but my boxers.
Laying on the bed nearly naked and blind I started to feel Amber trace her fingers up and down my body. I could tell she wasn’t fully clothed as her thigh or side would occasionally graze me. Whenever I reached up to touch her she told me to stop and that this first part was about me. She slowly pulled my boxers off and started to tease my cock. First with her fingers and then with her tongue making sure to lick my balls. She then proceeded to give me the best blowjob I had ever received. No teeth, soft and sensual, cupping my balls, and going deeper with every stroke. She then leaned down and pushed my legs wider and gave me the first rim job of my life.
It was finally now she removed the blindfold and I saw she had changed into a black lace thong and bra with garter belt and leggings. My mind practically exploded but she had to up the ante a bit more and asked me to stand up. I did and she moved to the edge of the bed hanging her head off the edge. “I can’t take you deep enough on the bed but I can here. Be gentle at first and if I tap your leg pull out.” This was new to me as well but she was already grabbing my ass and pulling my dick into her mouth. No more then 30s later I was fucking her face and she showed no signs of stopping. As I got closer I got rougher expecting her to tap out but she just got more into it. Finally I came down her throat and she gulped swallowing my cum and having me feel her neck muscles on my sensitive cock.
It took me a minute to recover before I started to return the favor. I stripped off that thong and turned her around starting out eating her freshly waxed pussy from behind. Learning a few tricks from her I teased her asshole as my fingers played with her pussy. We alternated from there to her sitting on my face grinding her pussy into me and finally to her on her back. She loved penetration as well so as I attempted to find her orgasm I was also gently fingering her slick pussy. She eventually came wrapping her legs around my head and almost screaming.
“I need you to fuck me” she said and popped up into doggy style. I took my position at the end of the bed. I slowly started to stretch her pussy out and within a few strokes was buried inside of her. Our bodies crashed into each other my legs slapping her thick ass and her tits bouncing. She screamed obscene things as I fucked her harder and harder teasing her ass with my finger. She leaned over at one point and pulled a metal butt plug out of her bag and told me to put it in. Using her juices and as I fucked her I slowly inserted it and she took it with ease. As it was going in she cried out that she was cumming and collapsed onto the bed my dick slipping out of her.
She shook for a few seconds regaining her composure before sitting back up. We sat there for a minute catching our breaths before she turned her attention to my problem. “I can last a while after the first time” I told her. She reached down and started to lick and suck on my cock for about a minute. I had thought she was going to try finish me off in her mouth but she popped off and started rummaging in her bag. “Sorry I just really like to taste myself afterward, I did an enema earlier today though if you’d want to try my ass”. She handed me some lube and we got to work her explaining to me how she liked to be prepared.
She got on her hands and knees on the edge of the bed again and had me remove the plug. I then coated my fingers in lube and slowly slid them into her tight hole. She took them with ease instructing me to spread the lube deep inside of her. I pulled out and walked over to her head asking her to revive my softening dick. As she did I slapped her ass and prepared myself for my first time having anal with someone experienced. After I was hard again I took up my position at her ass and coated my cock in lube. I positioned the tip at her waxed starfish and pushed in slowly. We took our time and at one point she asked me to stop and hold when we had about 2in in. “Sorry you are a bit bigger then I am used to just give me a moment”.
After a minute she told me to continue and we continued till I was buried in her ass. I started to fuck her very gently the way I did with previous inexperienced partners. She giggled “You know you can like actually fuck my ass not just massage it”. Gaining confidence I started to actually fuck her at a moderate pace. Having your dick in someones ass and gently moving in and out vs actually fucking are entirely different worlds. Prior to this experience I had not been sure if I liked anal but I was becoming a convert quickly. I slapped her ass going faster now as she cried out. “Use my ass, fucking make me your little cum slut you dirty fucker” she said as she rubbed her clit. I was getting closer and closer having never felt this combined with dirty talk I can never repeat. l I asked her where she wanted me to cum and she laughed again “You better not waste that cum on my back when I did all this work and you are fucking my ass so well”. This girl really was a freak and I gave her what she wanted fucking her ass hard her crying out. I was sure that the neighbors would hear she was being so loud.
I came rope after rope of cum into her ass as she cried out and her ass pulsed around my cock as she had another orgasm as well. I slowly backed out of her as she continued breathing hard till my cock popped out of that amazing ass. We chatted and laughed on the bed for a while before she got ready to leave and I walked her out and down to her car.
I headed back to the house and had a heart attack as I entered the door to Jackie sitting at the table a drink in her hand. She laughed at my expression and pushed another glass she had prepared my way motioning for the chair next to her.
“Sounds like you certainly had a good time you could give me a little warning next time” she said with a giggle.
“I swear to god I didn’t think you were home I am really sorry if it bothered you” – Me
“Oh I wasn’t, I got home from my spin class when I think you were eating her out from the sounds of what she was screaming.” – J
I buried my head in my hands mortified.
“I am really sorry again I hope you didn’t have to hear too much of it” – Me
“Well I really couldn’t help but hear everything it sounds like she was having an amazing time. I’ll never be able to look at my daughters bed the same way” she said still smiling
Having finally picked up that she wasn’t mad I started to flirt back.
“Hopefully it won’t be too traumatic, I am glad we were able to put on a good show for someone else” I said
“That is why I want a little warning next time I don’t want to miss the opening act. It was actually really hot to listen to. I’ve had a few let downs recently” she said as she rested her hand on my leg.
“Well as you can now know I’m not one to let a woman down if she can handle it. Not all of them can though” – Me
She ran her hand up to my cock and gave it a light squeeze.
“I think you would be surprised what I can handle with my experience. Are you busy this weekend I don’t think I have shown you our beach house. Unless you are too busy with that girl” – J
“Sounds perfect to me.” I said running my hand up her leg
Continued in part 2
Source: reddit.com/r/gonewildstories/comments/10q2ee6/mf_being_overheard_having_sex_by_my_almost
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