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C|SUITE LETTERS: Alpha Widowing A Widow

Alpha Widow

Alpha Widowing A Widow

Dear C|Suite,

I never thought I would be typing this to you all, but I have mixed feelings about what has transpired over the last few years. This letter is almost strictly my confessional, to cleanse myself of the fuck-a-bouts I probably (definitely) shouldn't have participated in.

For what it's worth, it actually feels cathartic to get this shit off of my chest as it’s not something I have ever shared. I figured, this one is for the C|Suite. Only sociopaths make it to the corner office anyways.

Let me start by saying that my closest friend was named Ray. We hit it off from the day we met back in college. 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 in life. 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 had played Division I volleyball for UCLA, 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 her husband and I were best friends and was very supportive of our friendship. Yeah, I know, a woman who was about a HB (hot babe) 9.8 and really cool to go with it—Pretty much any man's dream.

Anyway, they eventually got married and ended up moving cross country to Florida. Unfortunately, Ray couldn't have kids due to the chemo/radiation from his cancer treatment. His balls were basically scorched earth like Chernobyl.

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 me up one summer morning 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 eventually 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 that seeing her would bring back some painful memories; images and thoughts that I was reluctant to face.

We decided to meet in my hotel at the bar at 7:30 PM. 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. After walking in we had a really long hug, it was very emotional for both of us.

Her gorgeous eyes became dewy as she started to sob, and cried a bit while we hugged. I didn’t know what to say so I just whispered the words, “Fuck cancer..” to her. She said it right back. I don’t know why I said it. Maybe it was because that’s usually what people say now when a loved one has had cancer or is going through that. I think Tia even wore one of those T-shirts that said FUCK CANCER on it while Ray was going through it all.

Even though it doesn’t help anybody just saying the words, “Fuck cancer” and won’t stop it, it’s just a normie thing to do I guess in order to cope with the inevitable. 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 away how the hell that came to be. She explained when she was younger she was always focused on school, grades, extracurricular activities and volleyball, 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 were in my room, having a drink on the balcony and just having a really nice time. At one point, 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, but when she reached for my buckle. I took her hand away and explained that we couldn't, that it was just wrong; that we shouldn’t.

I’d like to stop the story briefly right her so I could make the note that telling her the words, “we shouldn't was almost like an aphrodisiac; she then started to rub my cock over my pants.

I guess it is true what they say, that your girlfriend or wife will bring her new boyfriend to your funeral.

At the time, during Ray’s wake, I didn’t realize how true this would become.

Next thing I know, I was pulling up her sundress and yanking her panties down like a horny teen. 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. She subtly pushed herself down and my finger eased into her ass, next thing I know she is cumming and cumming hard and loudly.

As I began to stand, she pulled me on top of her, pulling down my boxer briefs (pants came off during the pussy eating); she then yanked me by my shirt 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. Truthfully, it felt very much like lovemaking, coming home from an overseas deployment, type of 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 pull out now, I have to shoot" She grinded herself harder into me and I began to pump her pussy full. It was easily one of the biggest loads of my life judging by the cream-pie aftermath. The feeling of my cock still inside of her while the warm slug trails leaked down my shaft and streamed down my balls.


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, according to her mental gymnastics and female math.


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 didn’t 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. 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 pussy 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. However, my bounce back time is still pretty solid ...which I was going to have to be ready soon...because at this point she was slowly going up and down my cock while I am spreading her ass cheeks. so i can see her tight little asshole. "Jump off, I have to cum" I told her. Tia’s 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 again soon.

The next day I went through my early morning meetings with a sore cock, achy balls 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 PM again, so that we could just go out to dinner. So where not near my hotel room.

The morning quickly turned into afternoon, and the anxiety of the evening lurched forward every time I would look over at the clock. 7 PM rolls around and I am anxiously waiting for Tia, truthfully wondering if I should tell her that it was a big mistake we hooked-up and that we should go back to our "normal" relationship. The other thought I had though, and this was secondary to the former, was if I should just fuck her in the ass doggy style.

Fast forward to 7:45 PM, I went with choice B.

So, there I was back in my hotel room with Tia, fucking her from behind. And may I remind you that she has that volleyball player ass, and I am pulling her cheeks apart like two King’s Hawaiian slider buns, whist plowing her pussy, and wondering what her asshole would feel like.

 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 collapsed face down into the bed, ass still in the air, "Dont stop....keep doing exactly what you are doing…this feels really weird...I’m cumming, I’m cumming,” She moaned. I felt her gush out of her pussy. I started to rub my cock between her ass cheeks, really without thinking she would let me fuck her in the ass, more just because that nice volleyball player ass had me beyond turned on. That was when she said; "You can do anything you want to me" I wasn’t going to ask for a second confirmation.

I started fingering her asshole, and she spun around and started sucking on my cock. She then spat on her own fingers and rubbed it on her ass. I gently eased my cock into her ass, but it went in surprisingly easily. So now I was fucking my best friend's widow in her ass (something else i would find out later she had NEVER done) whilst palming her tits and rubbing them like I was trying to get a blue genie to appear before us. She loved her nipples being pulled on, HARD. I was yanking her nipples, fucking her ass, and 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, how degrading it is, how women like being treated like a series of holes, but I emptied my nuts into her ass hard. We rolled over and she laid on my chest.

I must have dosed off, because the next thing I felt was her mouth on my cock (yes, my cock that was recently in her ass, and yes my cock that wasn’t 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 was adamant about bringing her pussy to my face; she sat on my mouth while holding the headboard. Her pussy was intoxicating and I was drunk on it. That sweet yet musky honey was giving my face a shiny primer. She told me she was about to cum by stating, “I want to cum all over your cock." So, she positioned herself over my dick and sank down, and yes, it was still so tight, she felt amazing. She rode me like a cheap quarter-fed pony at the shopping mall and came really quickly.

After that 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 as if I was impaling an indigenous wagon burner during the frontier days. I started really fucking her hard and patriotically, my balls bouncing off her taint and asshole that I recently fucked. I absolutely filled that pussy to the brim, again. I can’t help it but I love looking at a woman's pussy whilst my cum is 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 could feel was a sense of guilt, with a side of sexual delight. A plate that I knew would be hard to digest in the following hours and days. I was/am a horrible person for defiling my best friend's widow. I had filled her pussy 13 times, her ass 3 times and her mouth once— an allegorical buffet of debauchery. I was so confused about how I was feeling: I didn't know if I ever wanted to see Tia again or worse, if I couldn't live without her.


Fast forward about 8 weeks, Tia and I had talked a lot. I don’t think either of us had any idea what we wanted to get out of this; but circumstances changed when I read the following text from her.

‘I am pregnant…‘

I actually dropped the phone like my previous moral compass that I had once carried long ago. What in the fuck? But what did I expect? I had came, what had to be a gallon in total, inside of her in the time span that I was there.

Did we think that it couldn't happen? Does Tia not know how to take a damn pill every night before bed? Is she worse than a senior in a retirement home? Fuck cancer, it’s ruining all of us now. Cancer did this. It’s not my fault. It’s a disease. It spreads to everyone, eventually. It affects people in different ways. Where in death, there can be life. Why 13 times? Would it have mattered if I had only fucked her pussy once, twice, three times? Did we both somehow want this? Was it fait? Why did I cum deep into her as humanly possible? I deep-dicked my best friend’s widow. Widow-dicked. There are 3.95 billion other women on earth.

Human existence is a flash in a pan. I am being punished for sure by a higher authority. She better not wear that stupid T-shirt anymore. Fuck slogans. Fuck ribbons. Fuck Tia’s pussy. Fuck everything in sight. I can still smell her pussy when I think about it. The hotel room’s Wi-Fi password. Tia’s mascara running down her face. Tears through the phone. Moaning in remorse. Moaning in euphoric bliss. I can’t tell the difference. My cum running down her chin. I tipped that bartender way too much. How much does it cost to raise a kid until 18 these days? What is with all the black people and gays in commercials now? Are single moms ever really single? Abortions, Hitler, who or what has killed more? Tia let me cum inside of her. So, you’re going to be a baby daddy. Can you alpha-widow a widow whose never had an alpha?

Let’s 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. The tears and sobbing that reminded me of the day Ray had passed. The sound of her crying was reminiscent of that type of pain. She had miscarried. I felt like the biggest scum in the world for somehow feeling relieved.

Yours truly Horny,

The Widow-dicker

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