Disclaimer: I’ve never written one of these but have been reading for a long while and jacking off to these stories. Thought I’d give one of my more recent situations a go. Its pretty long and might make you bored but if nothing else writing this in my mind helps me rehash some good memories
When I was young about 10 years old, my brother had a girlfriend(lets call her Sarah). They were together a few years – not sure how long but long enough for me to hit puberty and develop a crush on Sarah. I’m 30 years old now so my memory is hazy on details of his and her relationship. She is probably late 30’s now or maybe even 40. These encounters happened this year maybe 2 months ago or so. I think about it everyday. Never plan on telling my brother or any of my family, as I believe my brother has moved on but my family never liked this girl.(and even though I love my parents they tend to be judgmental and hold grudges) My brother is now married to someone completely different and has 2 kids.(so he shouldnt care right? IDK – dont plan on finding out LOL)
So, when I knew her back in the day when she was with my brother I thought she was pretty. Now that I’m older I realize my brother has/had low self esteem and never really got dime pieces. This girl is still very fuckable in my mind and because i had a crush on her when I was younger makes the situation that much hotter. Sarah is blonde, pale, really pretty blue eyes, decent sized breasts but not huge and I never realized it until later but she has a bit of a nice ass as well So, after they breakup social media becomes a thing. When I am in high school or college I find her on myspace and I don’t really remember the situation as to how we started talking but we end up flirting off and on. Myspace goes away and I find her on facebook eventually. After a breakup a few years ago I get really lonely and depressed and start hitting her up as i just wanted female attention. Our off and on flirting begins again but turns way more sexual. She starts telling me about graphic dreams she had about me fucking her and after I got older and she saw me around town she always knew she picked the wrong brother. The thoughts of getting with her really turned me on but in my mind was still more of a fantasy than reality. At this point I moved and lived about 2 hours away so we never really link up. I rebound my depression with another chick I meet so I stop talking to Sarah. Prior to my relationship that ended and had me in a depression I was shy socially and not confident with sex/girls in part due to inexperience. This relationship was kinda toxic it lasted nearly 5 years we lived together but didnt fuck that much. Anyways I didnt realize rebound chick at the time was a rebound chick and she was way more into me than I was into her. But she wanted to fuck way more than my ex so I finally got to try out a lot of my fantasies, etc. You can say I got in good practice and practice makes perfect right? So with all the practice my confidence in my sexual ability went up. Once I snapped out of my depression over the toxic relationship and I realize my rebound chick was a rebound(we were together a year- took me long enough right? I call it off. That was my bad because rebound chick was really sweet, just not the one for me.
The next point in my life is what some of my close friends and associates call my “hoe-phase.” ( If I write anymore I’m sure I will write about some stuff that happened in this phase. I justify my behavior as making up for lost time because in high school/college I rarely had these types of experiences due to being socially awkward and shy. I end up fucking lots of coworkers, people I met off tinder and other dating sites. I am pretty awkward in crowds and social settings so unless its a house-party atmosphere with friends I already know and am close to I usually don’t go out to like bars or clubs etc around a bunch of unfamiliar people. So most of the people I’m meeting are through online apps. Or people I already knew and reconnected with.(like sarah)
With the on and off flirting and communication with Sarah at some point we added each other on snap chat. One day I was bored in the office at work so I took a selfie and posted it to snap chat. Early the next day Sarah snaps me in response to my snap with the little emoji with the heart eyes. This is nothing out of the ordinary for us so I dont think too much of it but it had been a while since I talked to her and hearing and getting attention from her caught my interest. I am off work on this day with no plans or anything to do – in my mind I thought it was just going to be a boring lazy day. I don’t remember the exact wording of our conversation but we talk about how much we missed talking to each other and that we should catch up. I mention that I’m off work today and she should swing by and we can catch up(not really expecting her to come due to it being a week day and the distance between us). Sarah states that she has a lot of stuff planned that day so by the time she left she probably wouldnt get to my place until around 9 PM. I say thats perfect.
Despite our heavy sexual flirting in years past, our snap conversation was mostly just light flirting and being friendly but nothing too sexual. Sarah has always been a huge church girl (she even got my brother really into church)and atleast pretended to keep it classy in life, and me being shy didnt wanna risk offending her by being too sexual right off the bat even though I knew what I wanted. Sex doesnt come up, she is supposedly driving all this way just so we can catch up. the fact that shes driving all of this way to see me had me a little skeptical thinking it might be too good to be true – and knowing how heavily religious she is – even if she showed up I was thinking what I want to happen might not actually happen. So all day I keep thinking maybe she may not really make the drive. She snaps me that she is getting ready for church and sends me some pics. She will be heading straight to my place after church. I tell her how great she looks and that I cant wait to see her etc. After church she snaps me and asks where am I going? I send her my address and impatiently await her arrival. Time starts dragging by so slow!
When she snaps me that shes at my place I meet her outside. I give her a hug and smile but after asking her whats new and how was the drive I feel a little awkward. Not wanting to just go straight to my room and act like that was the only thing on my mind I ask if shes hungry but she just shrugs like she doesnt care. She knows from my snaps that I like to drink a lot and I live by a bar. I tell her about the bar and asks if she wants to go. She mentions that she doesnt usually drink a lot and has to drive home but we can go there to talk. So we walk to the bar I order a corona and she orders some kind of girly daiquiri. The conversation goes to her kids and I try to act interested but can only think about what her pussy tastes like. I order another corona and the bartender tells us they have jello shots for a dollar so I get us both one. She kinda looks at me crazy and says no more alcohol after that because she wants to be able to drive home. She has always been a little dramatic so she starts telling me about a lot of her problems including her most recent ex that she met in church. After listening to her drama about her ex, and one of her sons high school relationship drama, etc we finish our drinks. I ask her if she would like to walk back to my place and I could show her around and we can continue to catch up. We go on our way and as we get outside she says shes dizzy and stumbles stating that she hasnt drank in years so it must be the daiquiri and jello shot. I put my arm around her and feel her up a little(the alcohol reducing my shyness a little) and tell her I’ll make sure she doesnt fall. We get to my place and both sit on my bed. I pretend to act interested in her life asking questions but its mostly because I’m shy and procrastinating making a move. The topic of her mom comes up and she states that after church she lied and told her mom that she was going to another friends house instead of mine(because her mom remembers me but doesnt know we were in contact). I say well arent you a bad girl? and she just smiles and her pale face blushes. Her reaction gave me confidence to finally make a move.
I finally kiss her and immediately her hands go around me and shes kissing back. After a minute or so of making out with us both sitting up I push her back to where her back is flat on my bed and get on top and keep kissing her. After sucking on her lips and tongue for a while I start kissing her ears, neck pretty much everywhere all over and gradually keep going lower. Once I reach the bottom of her neck I raise her shirt up and start kissing around her breasts. She gasps and looks at me like she feels guilty but doesnt protest. I start sucking on each breast while my hand plays with the other one. This gets her moaning like she likes it so now I know it’s happening. Eventually I keep kissing her stomach and lightly sucking all over her body and until I reach her waist. I try to pull her pants off but have trouble because of how tight they are. She has the same guilty look on her face like she doesnt want to but she helps me take them off. I start kissing all over her panties around her pussy but over her panties. Finally I pull her panties off but keep teasing her. sucking on her thighs and kissing and breathing so close to her pussy. Finally I start sucking on her clit – she gasps. During my hoe-phase one thing I realized is how much I enjoy giving head. She is moaning while I am enjoying making out with her pussy. I insert two fingers in her and start massaging her G spot while sucking on her clit. This throws her over the edge her legs start shaking and she cums. I try to keep going but she pushes me away because she is sensitive. I go back up and kiss her so she can taste herself on my lips and her hands are all over me as we make out passionately. After a few minutes of kissing, She starts to mimic what I did to her – kiss me in the same places around my ear and neck as she goes lower and lower. As she reaches my waist I dont waste any time in throwing my pants and boxer briefs off. She starts licking and swirling her tongue on the head of my dick then down the sides and around the bottom until she finally puts her lips around my dick. She keeps going lower and lower on my dick until she has it all in her mouth. I always liked the idea of getting head from watching porn but never got with many people who made it feel great. She gave some of the best head i’ve ever gotten and gave the most effort and enthusiasm in pleasing me. After bobbing up and down and getting it all in her mouth a few times she stops looks at me and says its soooo big.(its really not its about 6 inches) I just laugh and say no its not and shes like yeah its literally hitting the back of my throat. She starts massaging my balls while she licks my dick and I’m loving it. She is basically making out with my dick so passionately with her eyes closed like we were kissing. Sometimes when I jack off I imagine her sucking my dick. I keep telling her Sarah you got this dick feeling right and Sarah you where did you learn how to do that baby?. She would look at me and smile when I would say stuff like that. She is getting my dick so wet and her lips bobbing up and down from the top to bottom of my shaft it gets me on the edge of cumming I didn’t even have a chance to warn her I just shot it all in her mouth but she takes it in stride like its not an issue. Once I’m done cumming She keeps sucking on my dick. My dick is really sensitive but she keeps sucking and I dont stop her- The idea of a girl having me uncontrollable at her mercy kinda turns me on and because I’m so sensitive I start shaking involuntarily while she keeps sucking my dick. I almost cant take it and am about to try to get away and she looks at me and was like is that good or bad? (referring to me shaking) and I’m like its just really sensitive – she says I know. then I pull her up to kiss me. We start making out again and I tell her “My turn to make you feel good!” She says no you already did! But I dove into her pussy and she didnt stop me. I ate her pussy and hearing her moan gets me hard again so while I’m eating her I’m jacking off until I am completely really rock hard. I get up walk around the bed to my drawer pull out a condom and get on top of her and put my dick in. She is soaking wet and her pussy squeezes around my dick. I slowly thrust in a few times and almost lose it. I pull out to regain my composure and just start kissing her like all is well. I get up off the side of the bed and tell her to turn around and back up toward me. She does and I start fucking her from behind while standing up. I start slowly and realize for some reason I’m readjusted better and able to last. So I pickup the pace. I alternate slapping her ass grabbing handfuls of it and grabbing her by the waist to pull and slam her back into me. She is being really loud. I rent a room and I’m pretty sure my roomates werent happy during all of this. But They cant say anything as they have some of their own stories.
While I’m fucking her from behind I start to admire how sexy this church girl looks on all fours taking my dick. This is when I realize her ass is actually bigger than I realized. (Sarah isnt thick but I really love thick girls with fat asses-I didnt know her ass was pretty fat until this moment)She has a tattoo but I don’t really remember what it was because it was dark but it was in the position of a “tramp stamp” All of the girls I’ve been with who have a tramp-stamp typically fuck pretty good – she is no exception. While I am relishing the fact that I am fucking my brothers ex that I always fantasized and had a crush on something comes over me and I feel way more into her than I should have.(Like I said she is pretty cute especially by my brothers standards but by no means a dime piece) I drop to my knees on the floor grab her by the waist and start eating her ass. I think this took her by surprise -Her moans become louder and while I’m doing this I start fingering her pussy. I alternate between eating her ass and sucking her clit. While I’m sucking her clit I stick my thumb in her ass and she loses it and cums all over my face. At this point we are really sweaty and she just collapses on my bed. I take my condom off without cumming in it. And get on the bed with her. She snuggles up next to me and we talk for a while. One of the things I remember her saying is “When I sent you the heart eyed emoji I didnt intend on ending up over here in your bed tonight” I was like well I’m glad you did. She says can I tell you something without you getting the big head? And I’m like sure – and she says of all the guys I’ve been with you’re dick is the biggest. I’m not saying this to brag because I know for a fact I’m not huge. But who gets told that by a girl and it doesnt make them feel good?
After we cuddle and talk about random stuff I’m still horny and turned on that this is actually happening. I’m enjoying her company and conversation more now. In the middle of our conversation I get more touchy feely and we start kissing and I eat her out some more. After I made her cum again she said “you do that like its your job and you love your job. ” I dont remember everything that was said that night but that will always stick out in my mind because I really do love eating pussy – so that was a good compliment I valued. I start sucking on her neck and shes moaning but says make sure you dont leave any marks. Even when I’ve tried I’ ve always had trouble giving girls hickies so I didnt think it would be an issue. I keep sucking on her neck and shes moaning – I’m rock hard and its starting to hurt so I put another condom on and ask how she wants me to fuck her. She just says however you want so I motion for her to turn her around again and enter her from behind. This was my favorite way to fuck her just seeing her on all fours throwing her ass back into me while i got to spank and squeeze her ass. I kept biting my tongue because I was trying to do anything I could not to cum because I didnt want it to end. This worked a little but finally I realized I couldnt hold it so I pulled out before she made me cum. I regain my composure lay down with my back flat on the bed and tell her to ride my dick.
She straddles my dick and slowly slides all the way down on it. As she does she makes a grimace like shes in pain. She then slowly starts sliding up and down on it. I get impatient as she is going really slow it doesnt feel so good so I grab her hips and start thrusting up into her as I pull her down on my dick. At first she starts acting like it feels good but then I see that same grimace looking like shes in pain. So I stop and let her do the work. She goes back to going slow. While shes fucking me slow her hands are carressing my chest and she says – you broke me. I said “naw baby you fuck me so good” I started sucking on her nipples but eventually got bored with how slow she was going. I flip her over and start fucking her missionary. She wraps her arms and legs around me and feels so tight from this position. I had to go slow to try not to cum. We start kissing as we fuck and the intimacy combined with her hands roaming my whole body was too much for me to take. I only lasted a few minutes in this position before I was cumming again. I pull out and take the condom off as we start talking. She checks the time and its 4 AM. She has to be at work the same morning plus make the long drive back to her area. So she gets dressed and I walk her out to her car. We kiss at her car and tell her I enjoyed hanging out with her and she says she did too. After she left a few minutes later she stopped at a gas station and snapped me a pic of her neck upset because I accidentally left a hickie on her neck. It must have been because her skin was so pale because I really wasnt trying.
We kept in touch briefly after that but it was understood that we could never be in a relationship hence the reason she lied to her mom about coming to hang out with me. But she did come over again the next week. The beginning was way less awkward we didnt go to a bar or anything went straight to fucking and the sex was just as good as the first time. I even got her to let me video her sucking my dick.(no dont ask for the video) . I jack off to it regularly tho. But it sucks that it probably wont happen again. Looking on her social media she is the type to cling to a guy who shows her interest. She mentioned to me that she hates that most guys dont think shes “relationship material” After seeing how good she fucks and sucks I really didnt want that to end so I was sending her snaps flirting with her but recently she started reacting differently. Come to find out she is in a new relationship. All of her facebooks posts are memes about being in a relationship and stuff now. Given her history hopefully this guy doesnt last – maybe I could have her again?. I’m always tempted to snap her and be like “can I tell you something without it going to your head? You gave me the best blowjob I’ve ever had”(The same way she told me my dick was the biggest shes ever had) But then I’m like naw just leave it be since she has a dude now. She sure gave me some good memories though. I wouldn’t say no if she broke up with him and called me and said lets fuck. But I really do wish her the best and want her to be happy.
Source: reddit.com/r/gonewildstories/comments/cliqoa/mf_the_time_i_fuckedmy_brothers_ex