This is my first story and it is based on a personal experience but it is not entirely true as I did add up to make the story better
I’m just a young boy and I’m about to turn 18 and my mom’s friend whose name is Lisa, actually I would call her Mrs. Carter but she insisted that I call her by her first name, i.e., Lisa she was in her 40s, she lived two houses away from ours and she has been friends with my mom since I remember, hot is one word I would describe her but I’ve never thought or felt that way about her because of how close she and my mom are. She does have a husband and she also has a daughter who is a one or two years younger than me but her daughter stays abroad with her grandparents and she would visit only during the holidays and Lisa had always looked at me a certain way, a way which no woman would ever look at a teenager.
One day my mom told me to go to her house and ask for some cornflour, Reaching her house I pressed the bell once and there was no answer so I did it again but still no one came out so I just decided to enter as I was entering I kept on shouting “Lisa are you home?” But she didn’t respond nor did anyone so I went upstairs hoping to see someone and entered the bedroom but no one was there and then suddenly I heard a noise coming from the bathroom and rather than calling her out I peeked just to check who was it and to my amazement there was Lisa taking a shower with the door half opened and my dick just went up and I got such a hard erection I was speechless at how hot and sexy she was, her boobs were huge and her nipples were the size of cherries I just couldn’t believe a middle aged woman to look so flawless, with firm breast and her pussy was hot pink in colour, I got so horny that I just wanted to touch my myself so badly and without any hesitation I pulled out my dick and started jerking off as she was taking a hot shower she, I tried to peep in such a way that she would not notice me and just as I was enjoying myself the unexpected happened, the fucking phone in the bedroom rang and she swiftly turned towards the door and saw me holding my rock hard cock she was so surprised and speechless, I just stood there for a moment with absolute shock and before she could say anything I just ran out of the room and out of the house and as soon as I reached home I just entered my room without saying a word to anyone, my mom called “Jayson have you got the cornflour I asked you to get?” I replied “No mom I didn’t go there” I also added that I was not feeling well just so she won’t disturb me, I sat in my room thinking, “Will she tell my mom?” I was so scared and I just couldn’t do anything so I played games and my dick was hard all the time and so I just started masturbating thinking about the shower scene back then after I came I just went down, had dinner and slept.
The next morning I woke up still feeling anxious about yesterday’s peeping but I just tried to shake it off, My mom shouted “Jayson you have to take the trash out get up it’s already 9AM” I just replied “I’m already up, wait I’ll come down in a minute” and I was really worried if by chance I meet or even see her outside so before going out I took a nice look outside just to check and she wasn’t there so I quickly dumped the trash and entered, it was a school holiday that day so I just sat at home watching movies and later in the evening I heard a door bell but my mom answered it and when I heard Lisa my heart started pounding but she was just having a normal chat with my mom and my name never came up so I was really relieved. After that for many days I tried my best to stay away from her to avoid an awkward encounter with her and it was fine I never met her until one day I was walking back home after school and just as I was about to turn left from the pavement I bumped into her and she saw me and we were face to face, I just stared at her for seconds didn’t know what to say and my mind was completely blank and she smiled at me and told me “I was surprised to see that Mr Doodle had grew so big, he was still small the last time I saw him” and she giggled (yes she was referring to my penis, I guess by last time she meant when I was a baby or a kid) I then gave an uncomfortable laugh and apologize to her saying “I’m really sorry for last time, I don’t know what happened I just …” I bumbled, didn’t even complete my sentence and didn’t say anything more and just walked away with embarrassment and then I walked home and I was kinda relieved now that I met her and that it’s settled but somehow I still felt scared thinking that she might tell my mom and as the days went on nothing really happened and I almost forgot about it.
One day my mom hosted a party, a dinner party and even Lisa was invited, she was the only guest who came four hours earlier to help mom out. After sometime my mom realized that some items were missing and she had to go all the way to the supermarket because the local store near our house was closed, it was a 10 – 15 minutes drive to the supermarket so in total she would take atleast 30 minutes. My mom left and told me “Lisa will be here so help her out if she needs anything okay” I simply replied “Yes mom”. After she left I was in the sitting room emptying the snacks into containers and she was in the kitchen frying bacon, attached to our kitchen there is a small storage room where herbs, spices, flavorants and other things are kept and I heard Lisa calling me from the storage room, she shouted “Jayson darling can you come here and give me a hand” I then told her “Just wait a second I’m fixing these tubes” and after doing so I immediately went to the storage room and as soon as I open the door, to my surprise I saw her standing there half naked with her dress pulled up showing her bare pussy and her massive boobs were dangling out, my first reaction was ‘WHAT THE HELL!?’ I just stood there and my mind completely blanked out, after seeing how astonished I was she then gently spread her pussy lips and showed me her insides, I could feel the growing bulge in my pants but I was not able to think straight and I murmured something like ‘Umm I think I should leave’ but at that moment she stopped me and told me “I know how badly you want this, after that peep show you enjoyed I want my fair share as well” after which she gave me a wicked wink, after hearing that it made me feel horny and I got off feeling a little bit ‘naughty’ but I did tell her “What about mom, won’t she be back after a few minutes?” “What if she catches us doing this?” and other such thoughts were running through my mind.
She calmed me down saying “It’s okay she’ll take at least 30 minutes, I know her way too well” *gives me a smirk* I then went towards her still astonish by the fact that my mom’s best friend is seducing me, she then guided my hand and placed it on her firm breast and I started squeezing them and I pinched her nipples which were erect. Before I could grasp and suck her amazing tits she forcibly pulled down my gray sweatpants and told me “It looks like Mr Doodle is very fond of me” and she got hold of my cock, the reference ‘Mr Doodle’ annoyed me a bit and I straight forward told her “Can you you not call it that, it sounds weird in like a bad way” she asked “What should I call it then?” after which she giggled I replied “Call it anything but not that” and then she was like “Okay but I still think that’s a nice name” *giggles* She started storking my dick and after three or four strokes my cock was full on hard she then licked the tip of cock and she was using her tongue vigorously and licking my tip in a circular direction and she grabbed my balls and rubbed them which gave me great pleasure, she teased my penis using her tongue and lips which was extremely arousing and she then she just gobbled my whole dick and I could feel her mouth and while my dick was inside her mouth she used her tongue to tingle the tip of cock and FUCK IT FELT GOOD!! She continued to go up and down on my cock and after that she just took out my dick and started giving me a boobjob and she teased the tip of my penis with her tongue I could feel the tenderness of her firm and massively huge breasts, she tightly pressed her boobs together and move them as fast as she could, squeezing my dick and then I got so aroused that I felt I was about to climax and I shouted “Ahhh Lisa I’m gonna cum” and I started to shoot cum everywhere even till the wall and cupboards behind but mostly on her chest. She then took a dab of my cum from her breasts using her fingers and swallowed it delightfully, it seems as if thought she had never got to taste semen in a long time. She jokingly told me “I love the taste of your hot & sweet juice, have you been drinking pineapple juice lately?” I just giggled and she added “Is that it? I thought we could have some more fun, shall we?” The first thought after hearing that was ‘I just fucking came all over your chest how on earth will I be able to get hard right after’ I directly told her “I had just cum I don’t think I’ll be able to get hard” But she gripped my dick and started stroking it, I remember the words coming out from me were ‘What the fuck are you doing!?’ She silently grasped my cock using both hands she furiously stroked my cock I felt so uncomfortable as I was still very sensitive but to my amazement I still got an erection not that hard though, she laughed and she exclaimed “There you go, you are such a stud young man..!”
She later turned back, bent over and spread her pussy right in front of me and told me “You can do whatever you want with it, don’t be shy” *giggles* I too then giggled and responded with an ‘okay’ I thought of directly plowing her but then I just wanted to have fun so I started off by spreading her pussy lips apart, I still stroke my dick just so that by any chance I won’t go limp and I inserted my tongue deep inside her and I rapidly tongue fucked her the best way I could, she moaned and her moans were so hot and sexy, she gave a loud moan and told me “Mmm yes that feels so good oh yess right there”
I inserted my index finger and started to finger her after sometime I immediately inserted both my index and middle finger and worked my fingers in and out of her very roughly and quickly and I twisted my wrists while doing so and she just grabbed my hand and she came, she fucking came while I was fingering her, that made me feel so good.
After a few minutes I stopped and told her that I was going to insert my penis inside her and the moment I told her that she said to me in sensual tone, “I have wanted you to be inside me for so long, I have always thought of you fucking me in every way possible” I was stunned for a second, hearing that but then I shook my mind off it and I asked her “But we’re not using protection, is that alright?” Cause I didn’t have a condom she responded “Jayson you’ve got nothing to worry about, just do it” Even though I was still a little bit worried, I became oblivious knowing that she’s a middle aged woman who knows what to do.
I pushed her vagina apart with my fingers and gently inserted my cock inside her and then my penis entered her vagina, she was unbelievably tight I couldn’t even shove my whole dick quickly all at once inside her because of her tightness I had to go slow, I lustfully asked her “How can you be so tight?” however she didn’t reply all she did was moan. I began plowing her and I could feel my dick throbbing inside her, it felt like silk it was amazing. My dick got harder with each stroke, I could literally feel my cock expanding inside her and stretching her mature yet close fitted pussy. I began to thrust harder and harder each time and I felt my cock poking her cervix which felt great, she was having a good time herself. I then pulled out my dick and just ram it up her pussy and ferociously thrust her will all my strength and stamina and fucked her as fast as I could even though my dick was still sore it was a bit uncomfortable but it felt amazing and pleasuring. She then shouted “Even my husband is not as good as you, you’re better than him” While fucking her I even tried to insert a finger or two inside her but that was not possible because she was too tight. She then told me “Stop, let’s change position, let’s go to the kitchen” I replied “Are you crazy!? What if somebody sees us? Or worse my mom catches us?” She just replied “No one will see us let’s go, this room is too small anyways” I hesitatingly agreed and went to the kitchen with her she then jumped on the counter with her pussy facing me, she then held my cock and guided it to enter her tight pussy, I could feel my dick sliding inside her vagina and I felt her warmness and how firmly her pussy was grasping my cock, the sensations were great. After a few minutes I asked her “How about you sit on the chair?” to which she agreed as she sat there, I grabbed her boobs and gently pinched her nipples and this gave her great pleasure, I could tell by her facial expressions and the way she was moaning and that position gave me control so I vigorously started pumping her with all the energy I have left and fucked her in the roughest way possible, in and out of her pulsating pussy, after just a few minutes I could feel the tension building up in my balls and I quickly thrusted her as fast as I could and I felt her vagina clenching my cock, as I was quickly pumping her I could fell the tension building up in my balls and I swiftly withdraw my cock from inside her and before I could even stroke my cock I squirted spurts of cum all over her and gave a loud moan, I was just as surprised as she was. She told me “Wow that was so hot, I didn’t expect that..! You’re quite impressive” I replied “Well I sure am impressive haha” *giggles*
After that she suddenly had a gloomy look on her face and she told me how guilty she felt because of how young I am and how close she and my mom are and she also added that her husband wouldn’t satisfy her in bed and that they were also having relationship problems, I then tried to cheer her up saying that we’re humans we all have our downfalls and I jokingly told her that I’m going to be eighteen in the next two months and she laughed. She told me “We should do this again sometime” and I smirked and replied “Yes sure, why not” but we kept that secret only between us. Later my mom returned and the party started but my balls were aching like hell and I felt like going nuts like literally lol but after sometime it subsided.