If It Hasn't Already Happened, It Will Tomorrow!

[CuckArtist]

Ok, so here’s what’s happening! My fiance and I have been dating since College orientation, and we just recently graduated. It has been four years of sexual frustration for her. All of her high school sexual experiences were with alpha male types, and here I am with a pencil-dick and a submissive beta personality. As her sexual frustration grew our relationship turned more towards femdom. We have never talked about cuckolding although it has long been a fantasy of mine, but she has gotten more and more into SPH, and facesitting. She is not shy about my poor sexual talents.


I’m a work from home artist, and she starts her new job across the country in September. We had to leave our apartment and didn’t want to spend the money on a new one for the summer, so we ended up staying with my friend James. Now, James is very much an alpha-male. Strong body and personality, charming, and well hung. He’s been a friend for a while, and I’ve seen and heard, how well the ladies like him. He came from money and has invested wisely, so now he’s basically swimming in cash.


We’ve been here for a month and it has been great. He spoils us with lunches and gifts. There’s a strong humiliation in another guy providing for your girl. Since I work from home, and they have a lot of free time, they’ve been hanging out together a lot without me. In the yard together, in the theater room in the basement, going to lunch and shopping without me. Saturday they are going out on his boat. I can’t come because I have a deadline to meet. I have seen a little bit of flirting, some from him that is just his natural personality, but I’ve seen her holding eye contact for a long time, biting her lip, and laughing too hard at his jokes.


The last thing is that she’s been nicer to me in bed. The SPH and femdom stuff has been drastically reduced. She seems a lot less upset that I’m bad at fucking. There has to be a reason for that. This is the ultimate humiliation for me. Not only is he probably taking care of her sexual needs that I can’t, he’s also providing her with a standard of living that I can’t.


I’m probably going to his deadline because all I’ll be thinking about tomorrow is them fucking on his boat.

 

[BigdaddyToronto]

on the positive side, maybe James can teach you to be a better lover...if they allow you to watch at some point.
IMO, youre too young to give up on sex.

 

[CuckArtist]

on the positive side, maybe James can teach you to be a better lover...if they allow you to watch at some point.
IMO, youre too young to give up on sex.

Thanks for the encouragement! It's worth a shot, I just think my personality is too submissive for her sexual interests. She wants to be pinned to the bed and choked and I just don't think I'll ever have that i me!

 

[CuckArtist]

Things are looking good. I checked the bag she was packing and there's a very slutty swimsuit in it! I also noticed she's bringing a regular pair of panties, but I'm not sure that means anything.

 

[Custer Laststand]

Ok, so here’s what’s happening! My fiance and I have been dating since College orientation, and we just recently graduated. It has been four years of sexual frustration for her. All of her high school sexual experiences were with alpha male types, and here I am with a pencil-dick and a submissive beta personality.

This seems puzzling. Why do you think your (now-) fiancé was initially attracted to you, and has continued dating you for the past 4 years....?

As her sexual frustration grew our relationship turned more towards femdom. We have never talked about cuckolding although it has long been a fantasy of mine, but she has gotten more and more into SPH, and facesitting. She is not shy about my poor sexual talents.

OK, if that's what works for the two of you (i.e., if your fiancé thinks, in fact, that's what works for her).

I’m a work from home artist, and she starts her new job across the country in September.

I gather, then, you will be free to accompany your fiancé to her new job location where you will also be able to work from home. If this is not the case, your fiance's move is likely to put a major (read, really large) strain on your engagement.

We had to leave our apartment and didn’t want to spend the money on a new one for the summer, so we ended up staying with my friend James. Now, James is very much an alpha-male. Strong body and personality, charming, and well hung. He’s been a friend for a while, and I’ve seen, and heard, how well the ladies like him. He came from money and has invested wisely, so now he’s basically swimming in cash.

Sounds like your friend James is independently wealthy as a young man. Must be nice....

We’ve been here for a month and it has been great. He spoils us with lunches and gifts. There’s a strong humiliation in another guy providing for your girl. Since I work from home, and they have a lot of free time, they’ve been hanging out together a lot without me....

James must have considered it a real score to have invited a friend (you, who has to spend all his time working) to have moved in — a friend who has (I infer) a gorgeous fiancé who is not working this summer, and who is thus free to spend all her time with him....

....in the yard together, in the theater room in the basement, going to lunch and shopping without me. Saturday they are going out on his boat. I can’t come because I have a deadline to meet.

Nice (from James' and your fiance's points of view)....

I have seen a little bit of flirting, some from him that is just his natural personality, but I’ve seen her holding eye contact for a long time, biting her lip, and laughing too hard at his jokes.

If you think all the time they're spending together does not include fucking, I'd say you're deluding yourself....

The last thing is that she’s been nicer to me in bed. The SPH and femdom stuff has been drastically reduced. She seems a lot less upset that I’m bad at fucking. There has to be a reason for that.

The most obvious reason would be, your fiancé no longer feels any need for concern about the quality of sex (or lack thereof) she's getting from you, because she's getting all the high-quality fucking she needs, among many other things, from James.

This is the ultimate humiliation for me. Not only is [James] probably taking care of [my fiance's] sexual needs that I can’t, he’s also providing her with a standard of living that I can’t.

Yes, it must be humiliating. But, I also suppose you must have realized all this would be not just a possibility, but likely, when you accepted James' invitation to move in with him with your fiancé.

I’m probably going to [miss my?] deadline because all I’ll be thinking about tomorrow [will be James and my fiancé] fucking on his boat.

Almost certainly, you have it right. That is what your fiancé and James will be doing. Whether you meet your deadline, of course, will be up to you. But, on the plus side, your secret fantasies about being your fiance's cuckold are being fulfilled — more completely, I would guess, than you ever imagined.

A possibility you might consider would be whether your fiancé might stay with James, thereby leaving you without a woman. This, however, might be less of a risk than it seems. If your fiancé moves across the country in September to accept her new job (whether or not you accompany her), then James — who, as you've said, has no trouble attracting women — will be free to move on to a different attractive and sexy lover, and you — if you accompany your fiancé to her new job location — will probably once again find yourself her cuckold, when she takes a new lover there. If you don't accompany your fiancé to her new job location, my guess would be, you may find your engagement will wither away as she finds sexual and personal satisfaction with other men.

 

[CuckArtist]

Hi Custer! You are right that this may be more dangerous than I think, but I'm banking heavily on us moving away in September, and the fact that James isn't one for settling down. So I think this may be the perfect no strings attached situation.

So, a little update. Last night she shaved her pussy bare, which has to be a great sign. Such an obvious sign in fact, you'd think she wouldn't have been so open about it. I woke her up for her trip this morning with oral sex. I told her I was ahead of schedule, thinking she might ask if I wanted to come along on the trip. She acted like she didn't hear me, and then asked if I wanted a handjob. I thought it was interesting that she gave me some SPH dirty talk, even though she had taken a break from it recently.

 

[Custer Laststand]

Hi Custer!

Hi CuckArtist!

..... I'm banking heavily on us moving away in September.

Since you're going to accompany your fiancé when she moves across the country to her new job location, that's positive, of course. (You didn't mention that in your initial post, but it's good to hear.)

And, the fact that James isn't one for settling down.

Yes, that's what it sounded like (as noted in my last paragraph, above).

So, I think this may be the perfect no strings attached situation.

Could be. James is in the desirable position, from his point of view, of having a sexually-attractive and beautiful (I gather) woman to fuck all summer, who is already committed to another man (you) who is not in a position to do anything about it, even if you wanted to, such that he doesn't have to worry about your fiancé becoming overly attached to him — i.e., he won't have to initiate an unpleasant breakup when he decides it's time to move on to another woman.

So, a little update. Last night she shaved her pussy bare, which has to be a great sign.

Maybe James requested that, if she hasn't done it previously....

Such an obvious sign, in fact, you'd think she wouldn't have been so open about it.

Maybe she considered it another way of taunting you, which she knew would turn you on....

I woke her up for her trip this morning with oral sex.

Very good. It was totally appropriate for you, as your fiance's cuckold, to prepare her in that way for her day, or weekend, with another man.

I told her I was ahead of schedule, thinking she might ask if I wanted to come along on the trip.

Wishful thinking....

She acted like she didn't hear me....

Of course....

....and then asked if I wanted a hand job.

That was very generous of your fiancé. I mean, she could have directed you to beat your weenie (then feed yourself and swallow your cum) as she prepared to depart....

I thought it was interesting that she gave me some SPH dirty talk, even though she had taken a break from it recently.

More taunting, to turn you on.... while also ensuring you will keep in mind her upcoming sexual satisfaction over the weekend.

I hope you manage to refrain from masturbating, while trying to imagine what your fiancé and James are doing, sufficiently to meet your deadline this weekend.

 

[CuckArtist]

So I didn’t post an update because I didn’t really have anything to say. I stayed in our room working when they got home, waiting for her to come in. She finally did after a shower. I asked her about the boat trip, but she didn’t have much to say. She told me being out on a boat isn’t very exciting, and all she did was sunbathe, read, and enjoy the view. There weren’t really any threads to tug on.


I was frisky but she wasn’t interested. We did have some fun though. I was on my knees eating her ass while she leaned over the bed texting people on her phone. She didn’t say anything to me, and as soon as I was finished she got up and walked out of the room.


That night we finally had intercourse as a reward for meeting my deadline. She wasn’t shy about the SPH, and asked me more than once if I was sure I was inside of her. I came after two minutes, and she said it was pathetic. For the first time, she pushed my head down to her pussy and told me to lick it up. So I did.


Two little things happened the next day. We needed batteries so we drove to Walmart. They sat up front like a couple, and I sat in the back like I was their kid. It was kind of humiliating.


Then, later that day, Maha went out for a jog. I was in the kitchen making a snack, and James was swimming nude in the pool. He gets out and comes in to get a beer out of the fridge. He isn’t shy at all, and just lets his horse cock swing in the air. He starts chatting with me as if he wasn’t nude.


I’m definitely chubby, and making a snack, and he starts talking about how I should eat better. Which I think was kind of dominating. Then he asks me, since I work from home, if I could help tidy up the place. Which is a very reasonable request, but also seemed like a very Alpha move. It’s only a matter of time before I’m mopping the kitchen while he fucks my girlfriend.

 

[Custer Laststand]

Hi CuckArtist:

Re.:

So I didn’t post an update because I didn’t really have anything to say. I stayed in our room working when they got home, waiting for her to come in. She finally did after a shower.

If your fiancé took a shower before even greeting you and giving you a kiss, that's a good sign she was making an effort (probably successfully) to eliminate the smell of another men — presumably your friend, who took her out for a day (or weekend) on his yacht — from her body.

I asked her about the boat trip, but she didn’t have much to say. She told me being out on a boat isn’t very exciting, and all she did was sunbathe, read, and enjoy the view. There weren’t really any threads to tug on.

Very good. If you didn't initiate an argument with your fiancé, you're showing good promise as her cuckold-to-be.

I was frisky but she wasn’t interested. We did have some fun though. I was on my knees eating her ass while she leaned over the bed texting people on her phone.

The most obvious explanation would be, she wasn't interested because she was sexually satiated. And, kissing your fiance's ass and giving her analingus (on your knees) while she was preoccupied texting her friends (updating them re. her fine yacht adventure, no doubt), was exactly the right thing to be doing as her cuckold-in-waiting. My congratulations to you.

She didn’t say anything to me, and as soon as I was finished she got up and walked out of the room.

Not surprisingly....

That night we finally had intercourse as a reward for meeting my deadline. She wasn’t shy about the SPH, and asked me more than once if I was sure I was inside of her. I came after two minutes, and she said it was pathetic. For the first time, she pushed my head down to her pussy and told me to lick it up. So I did.

All good. Your fiancé is responding to your sexual efforts in an appropriate way. She is telling you, in effect, where you stand with respect to her lover....

Two little things happened the next day. We needed batteries so we drove to Walmart. They sat up front like a couple, and I sat in the back like I was their kid. It was kind of humiliating.

The obvious humiliation secretly turned you on, I gather. Your fiancé understands you very well....

Then, later that day, Maha went out for a jog. I was in the kitchen making a snack, and James was swimming nude in the pool. He gets out and comes in to get a beer out of the fridge. He isn’t shy at all, and just lets his horse cock swing in the air. He starts chatting with me as if he wasn’t nude.

What the hell.... it's his house, dontcha' know....

I’m definitely chubby, and making a snack, and he starts talking about how I should eat better. Which I think was kind of dominating.

Yes, it was. But, it would have been a good suggestion coming from anyone. There are actually two requirements for getting control of your weight and starting to reduce it, thus becoming more attractive to your fiancé One is to eat better, but most important is to eat less. Factoid: the average American adult man, when body-mass index and height are taken into account, is ~25 lbs. overweight. (So you don't feel discriminated against, the average American adult woman is overweight by a similar number of pounds.)

Then he asks me, since I work from home, if I could help tidy up the place. Which is a very reasonable request, but also seemed like a very Alpha move. It’s only a matter of time before I’m mopping the kitchen while he fucks my girlfriend.

You have it right. But, doing the housework — perhaps eventually cooking the dinners, clearing the table, and cleaning the kitchen and getting the dishes washed — will be among your duties as your wife-to-be's cuckold, so she will have sufficient time and energy to go out with, and attain continuing sexual satisfaction with, her lover (or, in the future, lovers). So, you might as well get started now.

Finally: congratulations for meeting your work deadline, not allowing yourself to be too distracted by thoughts of what your fiancé and your friend might be doing while enjoying time together on his boat.

—Custer

 

[Custer Laststand]

CuckArtist,

Regarding the following, and your other descriptive comments:

That night we finally had intercourse as a reward for meeting my deadline. [My fiancé] wasn’t shy about the SPH, and asked me more than once if I was sure I was inside of her. I came after two minutes, and she said it was pathetic. For the first time, she pushed my head down to her pussy and told me to lick it up. So I did.

Your status as your fiance's cuckold-in-waiting has reached the point where you should probably start reading:

HotwifeLetters.com Index Page

(Or google HotwifeLetters dot com — the index page should come up as the first link). And, you might introduce your hotwife-in-waiting fiancé to this site, as well.

—Custer

 

[CuckArtist]

Just a couple of small updates!
We were in the kitchen and he got out of the pool and we could see his huge cock outlined in his wet bathing trunks. She said "So that's what a cock is supposed to look like." She laughed it off and kissed me, and said she was only teasing.

Then a few days ago they went out to dinner. (I was invited, but I had work to do.) she came home really late and I was already in bed. I asked if she wanted me to go down on her, like I do every night, but she declined. She did offer me a handjob. So we spooned and she jerked me off. It was nice and romantic. She said it makes her happy that I'm not crazy jealous, and I don't mind her hanging out with a guy. She liked that I didn't harass her with a bunch of questions every time she comes home. I told her the only question I'd ever ask her is "Are you happy?" She didn't say anything, she just kissed my ear and started jerking faster. When I came she put her fingers in my mouth so I could clean them.

They went out dancing last night. She came into the bedroom, stripped, and then climbed onto my face. Certainly a big change from last time she came home. She rode my face until she came. I asked for a handjob and she said I should have jerked off while eating her out, so I had to go to sleep still horny.

 

[Custer Laststand]

CuckArtist,

Re.:

"They [my friend and my fiancé] went out dancing last night. She came into the bedroom, stripped, and then climbed onto my face. Certainly a big change from last time she came home. She rode my face until she came. I asked for a handjob and she said I should have jerked off while eating her out, so I had to go to sleep still horny."

Very good. Queening you (i.e., mounting you and riding your face until she orgasmed) was totally appropriate for your fiancé after coming home to you, her cuckold, after a date with another man.

—Custer

 

[CuckArtist]

Well it's out in the open now! So I had been hard at work for a while and I went looking for her. I peeked out a window and saw her sucking him off. They were by the pool, and she was on her knees blowing him. That thing was huge, I couldn't believe she could even fit it in her mouth. Of course I couldn't look away. He looked up and we made eye contact. I thought maybe a bunch of drama was about to unfold, but no, he locked eyes with me, put this hand on the back of her head and pushed her down deeper on his cock. We kept looking at each other until he pulled out and came on her face. I ran away back to my room so she wouldn't know I was there.

So I'm pretty anxious and hiding, because I don't know what will happen if he tells her I was watching. Hours and hours go by. It's dark now and she finally comes up to our room. She's wearing nothing but a long button down men's shirt and she sits on the edge of the bed with her legs crossed. She tells me to kneel on the floor, so I do.

She said she was in James room and wanted to know if I knew what they were doing.

I said I did. She asked what, and I said fucking. She asked if I knew why they were doing that, and I said because I have a small cock and because I'm a pathetic beta male. She asked if I was ok with what they were doing and I said I was. She parted her legs and told me to prove it, so I ate her out.

Afterwards we got into bed and we talked a little bit. A bit about how much we loved each other, and a bit about how tiny my dick is. She gave me a handjob. She told me they were going to fuck out in the open and I'd have to just deal with it. She said I still had to prove I was ok with everything. She wanted me to buy them a box of condoms and make them a romantic dinner.

So that's what happened a few hours ago. I bought her condoms, I cooked them dinner complete with lit candles, and then I stayed in the kitchen while they ate. They went up to fuck and I cleaned up. Just now I came in here to write this up and they are still going at it.

 

[Custer Laststand]

Well it's out in the open now! So I had been hard at work for a while and I went looking for her. I peeked out a window and saw her sucking him off. They were by the pool, and she was on her knees blowing him. That thing was huge, I couldn't believe she could even fit it in her mouth.

Sounds like your fiancé has become a size queen. It's good to hear she had no problem fitting your friend's huge cock in her mouth.

Of course I couldn't look away. He looked up and we made eye contact. ..... he locked eyes with me, put this hand on the back of her head and pushed her down deeper on his cock. We kept looking at each other until he pulled out and came on her face.

Nice....

I ran away back to my room so she wouldn't know I was there.

Most likely, your friend told your fiancé you had been watching. It probably turned him on, so he came faster than he might have otherwise....

So I'm pretty anxious and hiding, because I don't know what will happen if he tells her I was watching.

He probably did (as noted above).

Hours and hours go by.

Probably both of them concluded there was no point in pretending further they were not fucking....

It's dark now and she finally came up to our room. She's wearing nothing but a long button down men's shirt and she sits on the edge of the bed with her legs crossed. She tells me to kneel on the floor, so I do.

Very good. You obeyed your fiance's order and assumed a subservient position....

She said she was in James' room and wanted to know if I knew what they were doing. I said I did. She asked what, and I said fucking.

Confessing you understood what your fiancé and James were all about was the right thing to have done.

She asked if I knew why they were doing that, and I said because I have a small cock and because I'm a pathetic beta male.

You could have said, "Because variety is the spice of life" — but no doubt your reply was more in accordance with what your fiancé was hoping for.

She asked if I was ok with what they were doing and I said I was. She parted her legs and told me to prove it, so I ate her out.

As your fiance's now-self-acknowledged cuckold, that was exactly the right thing to have done.

Afterwards we got into bed and we talked a little bit. A bit about how much we loved each other....

If your fiancé is still telling you she loves you, that's very positive.

....and a bit about how tiny my dick is.

Maybe you could have skipped that. Whatever size it is, that's what it is....

She gave me a handjob.

That was very generous of your fiancé. I hope you expressed proper gratitude....

She told me they were going to fuck out in the open, and I'd have to just deal with it.

This sounds very hot....

She said I still had to prove I was ok with everything. She wanted me to buy them a box of condoms and make them a romantic dinner.

Maybe when you buy a box of "Magnum" gigantic condoms, the check-out clerk will assume they're for you....

So that's what happened a few hours ago. I bought her condoms, I cooked them dinner complete with lit candles, and then I stayed in the kitchen while they ate. They went up to fuck and I cleaned up.

All good. But, It sounds like your fiancé is not on an effective form of birth control. Is that for religious reasons...? In any case, it's risky. It's more than likely she and James will soon begin fucking bareback, in which case there's a good chance she will become pregnant and give birth to his — that is to say, their — child after you've married her.

Just now I came in here to write this up and they are still going at it.

Excellent — clearly you have a sexually-satisfied fiancé. And, you're doing well as her self-acknowledged submissive cuckold. I encourage you to keep up your good work.

 

[BigdaddyToronto]

did she reveal to you when they first hooked up?

 

[CuckArtist]

did she reveal to you when they first hooked up?

No, but I'll ask!

Small update: I was out in the hot summer sun mowing the lawn and they were fucking with the window open. I had to listen to them the whole time. Pretty humiliating!

 

[Custer Laststand]

...... Small update: I was out in the hot summer sun mowing the lawn and they were fucking with the window open. I had to listen to them the whole time. Pretty humiliating!

Very nice....

 

[CuckArtist]

We had a nice romantic picnic together today. We discussed our wedding plans and we both agreed that this house and land was nicer than we could afford, and so we agreed to get married here before we leave in September. James agreed and now we're in a mad dash to get everything planned before the month is over.

 

[vahtcpl]

Sounds like you are proceeding carefully

 

[CuckArtist]

Small update:
We're getting married at the end of the month, and yesterday she asked me if I would wear a chastity cage until then. I would have liked to ease into chastity play, but I'm going to do two weeks straight!