u/Specialist-Worth-798

I’ve known my best friend since we were very young. she has a younger brother who I’ve known for that same amount of time. he’s always been a nice kid, early on I knew he had a crush on me but it was a cute one.

as we got older he didnt seem too popular with the ladies. He was very introverted and shy and didn’t seem to have much of a social life he spent most of his free time playing video games and watching anime.

I asked my friend if he ever brought girls around or had a girlfriend and she said no, that he rarely left the house if it wasn’t for work or school. When I was at the house though id often catch him checking out my ass and cleavage.

well for his birthday one year his family did a small get together for his bday he didn’t want anything major. Few cousins and aunts/uncles and I was invited also. Again I caught him checking me out a few times in the night but I didn’t care. I chatted with him and basically he never had even a date with a girl or a first kiss. I kinda felt bad for him, he wasn’t ugly but any means. Not gorgeous either but he wasn’t ugly, just shy and introverted. Before I left I told him to look out for a text from me soon. The next day I texted him telling him to stop by my apartment in the night and he did. I left the door unlocked for him and when he walked in I was waiting on the couch in matching lingerie for him. He was so shy and was caught between looking and looking away. I got up and walked over to him telling him happy birthday and that he could have all the fun he wanted to. After he got over his shyness we started.

we had some kisses, I blew him, we did doggy And missionary and then he finished so we weren’t able to try other positions but he loved it and I was just glad to help. his inexperience was obvious but cute.

while back I had a nasty break up with an ex. I was 19 at the time. he had cheated on me with a girl that was sort of my friend (obviously she wasn’t a real friend). it got ugly fights and it wasn’t amicable. I was so angry like I needed to get revenge somehow. I remembered though his dad always checked me out. while we were dating I just ignored it I didn’t care but I had been told him and his wife were already a bit rocky. I decided to starting showing up to some of the bars I knew he’d go to, wearing mini skirts and tight tops. he’d approach me and we’d chat, super sexually charged. he asked how his son and I were and I told him we didnt talk anymore which then made him get bold. he told me if I can keep a secret he would too, I was giving him all the signals and we ended up dipping and got a hotel to have some fun.

the sex was solid, ive had better but not bad at all. he had a bigger dick than his son actually which was hot and I told him and he seemed to enjoy hearing. revenge definitely felt good.

my dad and mom have been divorced since I was young. my dad never really dated much afterwards, he seemed to just be kind of disheartened by relationships it got ugly with my mom.

once I got older he confessed some things to me and opened up more I was always a daddy’s girl and super close to him. he told me that he rarely had sex. that he didn’t care for a relationship but he did hav needs and his hand got boring. he didn’t have much money to consistently pay for sex workers. I couldn’t help but feel bad.

Father’s Day was a few weeks later. for Father’s Day me and my siblings took him out to eat. I wore a shirt with extra cleavage to give him something to look at. when dinner finished and everyone said their goodbyes I told him to stop at my place. I hurried home so I could take my clothes off, underneath I had a matching lingerie set. i answred the door in the lingerie and told him “happy Father’s Day daddy“ and just stood there. he was there with his mouth wide open and in shock but I could see him getting harder. he asked if I was for real, if this wasn’t a prank and I told him it was real. that everh man deserves to be touched by a man and since he doesn’t have a girlfriend it was my job to help him out. he went to then start touching and we started having sex in my living room. he was like a dog with a bone he was so happy and like a horny young man. when we finished I cleaned up and he walked out with a smile from ear to ear.

ill be honest I’m most the hardest working person around. back when I was single I had first lived with a friend but didn’t like having to work 40 hours a week and pay bills z I had two guy friends that lived in an apartment in a nice side or town. I got closer to them and I started asking to go over more and more often. they always checked me out here and there I could tell they found me attractive. they weren’t ugly but I personally only saw them as friends but I saw them as ways to live rent free. I started hanging around more and more until I was almost sleeping there everyday.

one of my friends told me I was staying over too much and he didn’t mind if I moved in but would have to help. so I proposed him an idea, I told him if him and the other guy let me live rent free, I’ll be their free use doll. with only a few limits (nothing on my period not when others are around or I have plans, Sunday nights I can refuse)

he didn’t hesitate and agreed. he then told our other friend and he was a bit more hesitant and shy but when I told him I was serious he agreed to it.

we moved to another apartment with 3 bedrooms and they paid all the bills. I stayed at home, they’d have sex with me whenever they wanted. sometimes one right after the other. the sex wasn’t bad, I’d get a bit bored at times but they just wanted a release regardless how it came. I was milking them both usually twice a day. they also asked I walk around in sexy outfits so I mostly walked around in my underwear or sometimes topless.

last summer my husband was gone for about 2 weeks on a business trip. I was cutting the grass but I hate it. there is a neighbor that is young he’s about 18-19 years old. Due to this I thought hey he could probably take some cash. I asked him if he wanted to cut my grass for $40 and he said yes so the next day he came over and cut it. When he finished he knocked on the door. It had slipped my mind and I had no cash at all. He was nice about jt told me to just give it to him when I could but I said he had to leave with something. I made sure no one was around and I lifted my top and gave him a quick look.

he loved it, looked like he was in heaven. It took me back to my younger days of flashing guys haha.

my sister and her husband are celebrating their 10 year anniversary and she wanted to get him something special. she proposed to me a boudoir shoot. she said she wanted to give him something really sexy and have another woman included but she didn’t have any close friends she could ask. I didn’t mind and agreed to it.

we arrived at the shoot got our hair and make up done and we pretended we were just friends. we then put on our lingerie and did many different sexy poses at times kissing, touching each other’s boobs or ass, and even had some boobs in mouth photos.

she recently gave the photos to her husband.

no I won’t send the boudoir pics don’t ask.

my brother and his wife had gotten together young and were virgins when they met. they only had ever slept with each other so on their bachelor/bachelorette night they allowed each other that they could have sex with one person and no consequences. my brother invited his groomsman and a few other friends including me to a nightclub. the plan was he’d hope to get lucky at the club and if not we’d all pitch in to get him a sex worker.

well at the club we were all having a fun time and had lots to drink. at some point I was tipsy and started grinding on him. No one seemed to care and he seemed to love it so I kept doing it. All night I was on him with other people probably thinking I was his gf or something. He was touching my ass all night.

for as long as I can remember he’s found me hot I’d catch him checking me out often but we never did anything. Towards the end of the night he had struck out with many girls. I whispered to him “if you want you can spend your final night single inside of me“ he nodded like a puppy. We left and in the uber started touching each other. Almost with in walking into my apartment he bent me over and started fucking me. We did almost every position you can think of. He said he fulfilled a dream when he finished inside me

My husband has never been the jealous type. if anything he likes when another man appreciates me, it made him feel like he got a trophy.

we used to have friends who had a pool in their backyard and every summer we’d be there almost every weekend sipping on drinks and having a good time. it would usually be around 4-5 of my husbands friends and a few wives. I never liked tan lines and was always just someone that didn’t mind being topless. if I’m honest I never minded the attention either.

id often take my top off and just sit in the pool with my boobs out. the men would lose it. they couldn’t quit staring and my husband felt like the king. some women were in awe others supportive. one time one other wife took her top off but that was it usually I was the lone topless woman but it was fine by me.

my husband even “borrowed” me to his best friend a few times. I guess when they were in college they’d often share girls if the other hadnt had any in a while. his best friend was going through a tough divorce so a few times I gave him a bj and let him touch.

my son has always been more shy and reserved ESPECIALLY around girls his age. he never had brought home any girls or even gone on any dates to my knowledge. I’d ask him about girls and he’d tell he about a crush or two but it was always very surface level.

I’d catch him checking out my boobs or my ass if I had on leggings or shorts. I never minded looking doesn’t hurt anyone and I always felt he should be comfortable at home. when he realized I was just having a normal conversation he opens up and said no. that he never had sex and he badly wanted to try it. his eyes kept lowering to my chest. I just took a mental note.

his birthday we had a few family members over, his favorite food and some cake nothing crazy. he didn’t have much friends so not much people to invite. when everyone left i told him to go to his room and wait for me. I went to my room and changed into a sexy night gown that I hadn’t worn in a long time. it was a bit transparent so it gave a good idea of my body. I’m not the sexiest anymore but I thought he’d appreciate anything.

I walk over and don’t even knock I just walk in. he is sitting on his phone and when he sees me his eyes almost pop out. he’s speechless. I was holding another cupcake from the party and told him happy birthday, that tonight he became a man.

I then put the cupcake all over my boobs and told him to come eat it. he grabs my boobs and starts licking it up. before he’s finished eating it he looks at me almost as if he’s going to cry and says thank you. I kiss his forehead and tell him no need to thank me and to just enjoy. once he cleans up my chest and he feels all over I put him on his bed and suck his soul out. i edge him, he wasnt lasting long but I wanted him to experience his first orgasm inside a pussy. I lay down and guide him into me and he starts thrusting. He only got a handful before he exploded inside of me.

my dad and mom have been divorced for maybe 3-4 years now. my mom treats him like shit and I’ve always felt bad. I’ve always been a daddy’s girl and he’s always seems to treat me extra special.

recently we went out for dinner just to catch up. I had on a top with some cleavage but nothing crazy. I could notice he couldn’t stop looking. At first I didn’t mind I’ve caught him doing it before, but at times he was for real zoning out just looking at them. I giggled and told him “hey dad up here“. he apologized and but I found it funny. I then asked “haven’t seen boobs in a while or what?” it was rhetorical but he actually responded yess. he lives with 2 other guys his age and he said he’s just been so long without sex that it’s hard to not look. I was shocked but felt kinda bad. when we finished the dinner I hopped in his car and told him to find a secluded spot. he did and I take my top off and tell him he can look at my boobs whenever he wants. he touched them and felt them for a while as I started stroking him. I then leaned over and gave him a blowjob. he lasted only a few minutes, he clearly needed it. I swallowed every drop.