Fucked my best friend’s widow, and knocked her up [mf]

So, it seems like this throwaway is going to be used almost strictly as my confessional, to cleanse myself of the fuckings I probably (definitely) shouldn’t have participated in.

For what it is worth, it actually feels cathartic to get this shit off of my chest as its not something I have ever shared.

Here we go…my closest friend was named Ray. We hit it off from the day we met, coincidentally because I banged one of his best friends girlfriends, and Ray confronted me on it….but that is a story for another day. Anyway, Ray and I became the closest of friends and shared all of the good and bad that we all go through. When we were about 23, Ray got a rare form of cancer- luckily he went into remission and was fine….for awhile. 

Ray ended up marrying an absolutely beautiful girl named Tia. Tia played Division I soccer, and had the ass you would expect from someone who trained that hard with their legs. She also had big, beautiful tits-real ones- size D, long blonde hair, and blue eyes-she was fucking hot and even Ray used to say he had no clue how he landed her. Tia was always really nice to me, but never in an inappropriate way. It was like she realized and respected that me and her husband were best friends and was very supportive of our friendship. Yeah, a woman who was about a 9.8 and really cool to go with it. Pretty much any man’s dream.

Anyway, they ended up getting married and ended up moving cross country. Unfortunately, Ray couldn’t have kids due to the chemo/radiation from his cancer treatment. Through the years, we would all make trips cross country to visit, and in all truthfulness they always seemed really happy. Though we didn’t hang out the way we once did due to the distance, we were still the best of friends and confided in each other. After being married about 8 years, Ray called and told me the cancer had returned. I was gutted. I could go into all of the details, but honestly, they are too painful. I lost my best friend in his early 30’s. 

Let’s fast forward to 2 years, after Ray died. I ended up having to travel for work to the city Tia was living in; I was going to be there for 6 days. I called her to let her know I was going to be in town and we decided to meet for dinner the second night. 

Honestly, I had mixed feelings on seeing Tia; while I was close to her to and genuinely wanted to see how she was doing, I also knew seeing her would bring back some painful memories that I was reluctant to face. We decided to meet in my hotel at the bar at 8:30. I got there a bit earlier than I had expected as my meetings ended early. I got to the bar and grabbed a table in the corner and ordered a drink; then Tia walked in. I hadn’t seen her in 2 years and she was even more beautiful than she was before. She walked in and we had a really long hug, it was very emotional for both of us. We sat down and caught up; I apologized for not being there more for her, which she graciously said she understood. 

Somewhere through that dinner it was almost like we forgot the context of our previous relationship. I asked her about her love life and if she were dating at all to which she replied that she hadn’t been on a date since Ray. I said, “trust me, he would want you to be happy. You have to promise me that you will at least try.” Her response floored me, “I know that I should move on but Ray was the only man I was ever with.” I had to ask for clarification: Was Ray the only man you have ever had sex with? The answer: yes. 

I asked right a way how the hell did that happen, and she explained that when she was younger she was always focused on soccer so she didn’t have those wild college years that many have and then she met Ray.

Honestly, I do not know how we ended up there, but now we are in my room and having a drink on the balcony and just having a really nice time. Then she got really close to my face, and I leaned in to kiss her on her forehead, but she moved and brought her lips to mine. We immediately started to make out passionately, and we moved to my bed where we continued to make out. I really thought this would be as far as it would go, when she reached for my buckle. I took her hand away and explained we couldn’t, that it was just wrong. Guys-NOTE- telling her we shouldn’t was almost like an aphrodisiac, she then started to rub my cock over my pants. Next thing I know, I pull up her sundress and pull her panties down and i knelt in front of the bed and pulled her to the edge where I began to devour her pussy with my tongue. I began to lick and suck on her clit while gently putting my finger against her asshole and she subtly pushed herself down and my finger eased into her ass, next thing I know she is cumming and cumming hard and loudly. I started to stand up and she pulled me on top of her, and pulled down my boxer briefs (pants came off during the pussy eating), and pulled me down on top of her. She took me by my cock and rubbed it up and down her pussy as i slowly entered her. Tight isn’t even the word. Her pussy was so tight that I could have busted without even moving. I went really slow to give her a chance to get used to feeling a cock inside of her again, we kissed passionately, and truthfully it felt very much like a lovemaking session which is so unlike 90% of the sex I have had in my life. I rolled her over and wanted her on top of me so i could see those big, perfect tits…this was a mistake as she was grinding her clit into my pubic bone I began to feel that urge in my nuts….”I am going to cum……”…..I think i said it like 3 times and followed up with “i have to pulll out now, i have to cuuuuummmmm”….She grinded herself harder into me and i began to pump her full of one of the biggest loads of my life. 

Tia stuck her tongue in my mouth and we made out a bit, until my spent cock finally came out of her and I could feel a pool of cum dripping out too. We lay in bed talking for awhile when she got up and asked to use the shower. I escorted her in and she pulled me in with her. While we were soaping each other off she casually mentioned that she wasn’t on any sort of birth control (Ray was sterile). But she said that she had recently gotten over her period so we would be ok. 

We talked in the shower, we actually shed a few tears talking about the old days, but it wasn’t long before I had her bent over and was eating her pussy from behind (which is my absolute favorite thing to do)…and then i went to lick her ass. She immediately tensed up and said that she had never had her asshole licked before; another one of my all time favorites. When I assured her we were in the shower and she was perfectly clean, she relented and let me go to town! It didnt take long before she was really getting into it, so much so that she was bent over and pushing her pussy and ass into my face while i held onto her big tits for dear life! This went on for awhile, and eventually she came so hard her knees buckled. I sat down on the shower seat and pulled her onto my hard again cock. The view of her asshole while she went up and down on my dick was enough in itself to make me cum. I will admit this- I am not one of those guys that can pound a woman for an hour and not cum. I guess we all have different talents, and what I can do is get hard again quickly…which i was going to have to soon…..she is slowly going up and down my cock while i am spreading her asscheeks so i can see her tight little asshole….and there it goes, “jump off, I have to cum”…Her response, “fill me up, baby”. That is all it took, and i came harder than the first time, and she just kept slowly riding me trying to squeeze every ounce of cum out of me that she could. Eventually, we got up and showered off in the now ice cold water, and went back to bed. We fell asleep with her head on my chest. When I woke in the morning, she had left a note saying she had a great time and would love to get together that night….

I went through my early morning meetings with a sore cock and a guilty conscience. I had treated my best friend’s widow like a receptacle for my cum. I felt terrible. I felt so bad that i texted her to meet me at my room around 7, and we could go out to dinner.

7pm rolls around and I am anxiously waiting for Tia, truthfully wondering if I should tell her that it was a big mistake and we should go back to our “normal” relationship or if I should fuck her in the ass doggy style. Fast forward to 745: I went with choice B. I am fucking her from behind, and i remind you that she has that soccer player ass, and i am pulling her cheeks apart, while plowing her pussy, and wondering what her asshole would feel like. Uh-oh- damn it, how is that i have to cum already? I slowed down, pulled out of her and started eating her from behind while sucking her clit and rubbing inside of her, under her pubic bone….All of a sudden she fell face down into the bed, ass still in the air, “dont stop….keep doing exactly what you are doing….this feeeeeelsss really weirdd………….im cummingggggggg, im cummingggggg, and i felt her gush-not squirting, but no other way to describe it but gushing out of her pussy”. I started to rub my cock between her asscheeks, really without thinking she would let me fuck her in the ass, more just because that fat (good fat) soccer player ass had me beyond turned on….but that is when she said, “you can do anything you want to me”……I wasnt going to ask for a second confirmation. I started licking her asshole, and she spun around and started sucking on my cock hard, and then spit on her own fingers and rubbed it on her ass….I gently eased my cock into her ass, but it went in surprisingly easily. I am now fucking my best friend’s widow in her ASS (something else i would find out later she had NEVER done)…..I am pulling on her tits. She loved her nipples to be pulled on, HARD. I am yanking her nipples, fucking her ass, and I announced i was going to cum…..For those that have done it, there is nothing like cumming in a woman’s ass….I dont know, maybe it is just because how “wrong” it is…but i emptied my nuts into her ass hard. We rolled over and she laid on my chest…..i must have dosed off, and next thing i feel is her mouth on my cock (yes, my cock that was recently in her ass, and yes my cock that wasnt washed….no judging)….she sucked me back to life, and then climbed to where i thought she was gonna sit on my cock, but she brought her pussy to my face and sat on my face while holding the headboard….her pussy was intoxicating and i was drunk on it…she told me she was about to cum but wanted ” i want to cum all over your cock”….she positioned herself over my dick and sank down, and yes, it was still so tight, and felt amazing…she came really quickly, and said she wanted me on top of her, I stood at the edge of the bed and pulled her to me and jammed my cock in her and started really fucking her hard, my balls bouncing off of that asshole that I recently fucked, and here I go again….filled that pussy to the brim. I cant help it but I love looking at a woman’s pussy and my cum dripping out of it…I sat and stared…We eventually got in the shower and went out to dinner.

We repeated these events the rest of the nights I was in town….By the time I got on the plane all I knew was: I was/am a horrible person for defiling my best friend’s widow. I had filled her pussy 13 times and her ass 3 times and her mouth once. I was so confused about how I was feeling- didn’t know if I ever wanted to see Tia again or if I couldn’t live without her…

Fast forward about 8 weeks, Tia and I had talked a lot. I dont think either of us had any idea what we wanted to get out of this; but circumstances changed when I read the next text.

‘I am pregnant.‘

I actually dropped the phone. What in the fuck. But what did I expect? I had cum what had to be a gallon of cum inside of her in the time I was there. Did we think that it couldn’t happen? Did we think it wouldn’t happen? Did we both somehow want this? Lets just say my “circumstances” weren’t conducive to knocking Tia up….and a few days later, Tia informed me she wanted the baby. Holy fuck. She said that she probably wouldn’t ever get married again and this was her best chance at having a child. 

There is a lot i am skipping, but about a month later she called me in tears saying that she miscarried….i felt like the biggest scum in the world for somehow feeling relieved….

Anyway, eventually i will finish this off as there is much more to the story. Yes, that wasnt the last time that my cock was in my best friend’s widow and yes, I still feel terrible about it.

Source: reddit.com/r/gonewildstories/comments/glt7ln/fucked_my_best_friends_widow_and_knocked_her_up_mf