Little steps

[Baredare]

Two years ago I posted in a new members section asking for some tips on how to improve our sex life and get things going. Sex wasn't bad by any means, but my wife is pretty conservative, and sex was vanilla. One of the biggest tips was to get a dildo.

She was reluctant at first, but slowly she accepted the idea of trying it. She was shy at first, so we bought a small lipstick vibrator, which was more for clit play, and it didn't do much for her. I asked her if she wanted another one and presented her a few choices. She was reluctant at first but after some thinking picked the biggest one. She told me she didn't want to make the same mistake by buying too small again. That thing was way bigger than me (I am 5 inches long and just a little over 1 inch in diameter vs. 7 inches of insertable length and 1.6 inches in diameter). When it came, we realized it was pretty rigid, and she had trouble taking it in her pussy, but on rare occasions when she managed to relax enough, it would cause pretty long and intensive orgasms. I loved it. Sex after it felt way different. It would leave her stretched for a few days. Unfortunately, she was rarely in the mood for it, so I suggested we get another one a bit softer.

We ended up picking two more models. A realistic-looking vibrator and dildo. The vibrator was a bit smaller than the one she already had that was softer, and the dildo was more flexible and slightly bigger. She was first drawn to the realistic one. It was still a tight fit, but after a few times, she got used to it and was finally enjoying it. Only when the battery died did she remember that she had a dildo to try.

Only when I saw it next to me did I realize how big it was. About 8 inches plus the base in length and 1.8 inches across. I was honestly nervous about pushing that in my wife's pussy. She asked me to prepare her pussy by fucking her first. The whole time I was trying to slightly change the angle to help her pussy stretch. After a few minutes I stopped and took the dildo. It was huge. I put a good amount of lube on the dildo and her pussy and started to play. I let the head slide up and down between her pussy lips, letting it occasionally slide against her opening, and she took my cock and began to play. When her moans grew louder, I started to gently push it against her opening. I felt the resistance but took my time till I felt the pop. Her eyes widen, and I know the head was in. I slowly pushed more and more until it was halfway in and used another hand on her clit to make her relax. I was fascinated that she was able to take it. I could see she was somewhere between pain and pleasure, but it didn't take us long till we both reached explosive orgasms.

Next time she also forgot to charge her vibrator. Not sure if it was on purpose or not, but we used the dildo. I realized the change in her behavior. Previously I had to ask her if she wanted me to bring the toy into the bed, and she was often reluctant about it. Now she would bring it almost every time. Even if we just had regular sex. When I wanted to use it on her, she would ask me to fuck her for a few minutes to stretch her pussy, and then she would let me fuck her with it. Her orgasms were more powerful with the dildo, and our sex life became better. One time we were fucking, and she asked me where her friend was, so I reached for the dildo and pushed it in her pussy instead of my cock, and she came seconds later. We continued to call it her "friend." I would usually say something like "Is your friend stretching your pussy?" or "Spread your legs for your friend," which worked well for her.

She even hit the gym and lost a good amount of weight she had gained during pregnancy. We recently even talked about her going topless/nude on the beach. She gets turned on by the idea but is not fully comfortable with it. She is a bit concerned that I would look at other women at the nudist beach, and she is not too sure she wants to be seen by so many people there. She would probably be more relaxed if we were alone and wouldn't mind if someone just passed by. Unfortunately, you can never know how crowded it will be on the beach, and it is hard to find the spot that is kind of private. She also wanted to get a few new toys. She thought about getting a bigger dildo. She saw one with an unusual shape, like a monster or dragon, claiming she doesn't have anything like that. She also liked the remote-controlled one that you can put in your panties and turn on with the remote.

She is not into anal, and I'm not sure how to win her over about that. We tried it once a long time ago, and she didn't like it much. Said it felt like she had to go to the WC. Also, I'm not into the humiliation part of cuckolding. More like, I think it would be hot to share her or try a threesome if the right situation came. Not sure where to go from here. If you have any tips for toys, anal, sharing, or anything else, I would like to hear it.

[leggysman]

Another little step to try might be to get a small butt plug (possibly like this one viewtopic.php?f=9&t=67265&start=450#p1412421)

They're not 'challenging' to insert, and can be worn relatively comfortably even whilst out and about which is interesting. Try it yourself. I found I was kind of low-level aware of it the whole time, which made me horny. [ my wife happened to be elsewhere in a hotel room fucking someone at the time, which also made me horny ].

My wife sometimes wears one to a date, whether or not she's expecting to do anal. It is useful to warm her up for anal, but she sometimes just likes to have it in while having vaginal sex.

[Baredare]

She sounds like a sweet lady. I read quickly, but I didn’t see mention of you giving her lots of oral attention. Perhaps licking her thoroughly until she’s really wet and then introducing her ‘friend’ might improve things. Maybe calling it her ‘boyfriend’ or her ‘lover’ might be even hotter and introduce the hotwife element

She is definitely is. Unfortunately she is reluctant about oral. She came few times but it seems like it's never good time for it. Her pussy is not smooth enough or she is going to see red in few days, or she is not in the right mood for that etc. Maybe I should insist more.

I might try, but it might be too personal for her. As you said she is pretty sweet and caring and it might raise the questions.

@leggysman I'm not sure how I would talk her into trying it. She considers anal dirty and uncomfortable.

[rogerg]

I highly recommend taking everything at her pace, even if it seems like you aren’t making any progress.

In our case my wife loves when I perform oral sex on her, especially if we have been talking about our fantasies and she is already turned on. If I lick and suck on her, pausing frequently to describe one of our fantasies , she gets very wet and open and can easily take every dildo we have tried (we only own one and it’s medium sized, but we also use other objects.). My favorite to watch is a large banana. I like to insert it about half way and then just leave it there while I concentrate on the rest of her body.

The one dildo we have is a straight semi firm silicone one that is about one and a half inches in diameter and about 5” long. I can push it entirely into her until it completely disappears.

Have fun and keep us posted.

[Baredare]

I think we are making some progress. She started to buy more revealing clothes. She was trying new skirt last week and was telling me she likes it very much but she need to be careful not to show too much or her ass. Whole time she was smiling. Then she tried a shirt that was showing good portion of her tits and commented: "Should I get this one. I bet it will draw some attention." I told her it looks sexy so she decided to buy both pieces.

She was also curious to get a U shaped vibrator that was in her while I fucked her. When I asked her if she liked having two cocks in her pussy she barely managed to say yes as orgasm hit her. Then we got a soft dildo that attaches to the cock. It was tricky to use but I could feel the tightness of her pussy and she came fast but it felt like she was ashamed of her orgasm.
We talked again about visiting nude beach and she got wet, but is still reluctant to pull the trigger. I'm curious to see where will this take us.

[CuriousHusband91941]

Soft dildo that attaches to the penis? I need to find this and see how it works.

[kokomo21]

Slow and steady wins the race, next time she asks for her “friend “ say “ you mean your boyfriend?” Then leave it at that, then when she’s building up with it, go up and tongue her clit, this will drive her crazy, you need to let her think everything is her idea, and at her pace, I guarantee before long she’ll be asking you if you would like to tongue her while someone else is fucking her

[kokomo21]

Slow and steady wins the race, next time she asks for her “friend “ say “ you mean your boyfriend?” Then leave it at that, then when she’s building up with it, go up and tongue her clit, this will drive her crazy, you need to let her think everything is her idea, and at her pace, I guarantee before long she’ll be asking you if you would like to tongue her while someone else is fucking her

[BallSpanking]

She seems still shy about exposing more of her sexy body.
It sounds like she needs your encouragement, so she understands this makes you very proud of her.
Let her know it turns you on to see that other men appreciate her. And if they also turn her on,
it means her efforts are succeeding, so that's fine too.

[Baredare]

Thank you for replies. You are probably right. It need to be slow but steady. She probably needs more encouragement. She is still too shy to be open about it, but I can see changes in her. Dresses more sexy, likes attention, is more into sex and so on. I am wondering what is the next step.

[BallSpanking]

Buy her a new wardrobe, sexier than she would get for herself (don't make her look like a full time slut, just an irresistible young wife).
Encourage her to flirt with guys she finds sexy, and importantly ... texting with them.
Once she is comfortable mentioning them to you, you can slip in his name into your tale of her seduction at his hands ...
As you lick her pussy, and she will cum, and she will associate those delicious thoughts with that image ...

That might be a start.

[Baredare]

Things are slowly progressing. She is ordering more revealing clothes, talks more about sex and notices and coments the look of other people. What is more surprising she comments on both sexes. She picked a new dildo - the monster one. It came yesterday and it is huge. I thought there was no way she can take it but she did. She said at one point that it was too big and was hurting her pussy, so she asked me to put my cock in her. After just few strokes she told me she can't even feel my cock so I stopped and she jammed the dildo in her pussy once again. It looked so obscene stretching her pussy past her limit. She told me it felt like it's tearing her pussy apart, but she never stopped. She kept pushing it back in in short jerky strokes. She came hard which caused me to shoot my load all over her nude body. I hoped to see her stretched hole but she closed her legs probably feeling guilt for everything that has happened.

[BallSpanking]

I hate to be a party pooper, but if she becomes used to those unnaturally large things ... Her days of fucking men, you, or even other men with larger cocks are over. It becomes academic. What use will she have for human cocks if they are unable to stimulate her pussy??
This could lead to a dysfunction down the road (if not already).

[mundyman]

Things are slowly progressing. She is ordering more revealing clothes, talks more about sex and notices and coments the look of other people. What is more surprising she comments on both sexes. She picked a new dildo - the monster one. It came yesterday and it is huge. I thought there was no way she can take it but she did. She said at one point that it was too big and was hurting her pussy, so she asked me to put my cock in her. After just few strokes she told me she can't even feel my cock so I stopped and she jammed the dildo in her pussy once again. It looked so obscene stretching her pussy past her limit. She told me it felt like it's tearing her pussy apart, but she never stopped. She kept pushing it back in in short jerky strokes. She came hard which caused me to shoot my load all over her nude body. I hoped to see her stretched hole but she closed her legs probably feeling guilt for everything that has happened.

Enjoy this journey with your wife as she is willing to do and talk about things most wives won’t. Being receptive to your ideas, playing with sec Troy’s, dressing more sexy, working out, losing weight….
If you go out on date nights you might suggest going to a bar, club, or festival where there are available men, and women(?), and let her see how many might approach her. Of course you are nearby watching. Tell her she can be as flirty as she wants. Have a pre planned signal if she wants you to bail her out. Or text her during the night and can tell them she is talking to the babysitter.
It could be fun for you both, it could be a confidence booster for her.
But as been shared here by others, slow and steady wins the race. You’ve planted the seed, it seems to be growing, and now you need to nuture it
Good luck and please continue to share your story.

[mundyman]

Things are slowly progressing. She is ordering more revealing clothes, talks more about sex and notices and coments the look of other people. What is more surprising she comments on both sexes. She picked a new dildo - the monster one. It came yesterday and it is huge. I thought there was no way she can take it but she did. She said at one point that it was too big and was hurting her pussy, so she asked me to put my cock in her. After just few strokes she told me she can't even feel my cock so I stopped and she jammed the dildo in her pussy once again. It looked so obscene stretching her pussy past her limit. She told me it felt like it's tearing her pussy apart, but she never stopped. She kept pushing it back in in short jerky strokes. She came hard which caused me to shoot my load all over her nude body. I hoped to see her stretched hole but she closed her legs probably feeling guilt for everything that has happened.

Enjoy this journey with your wife as she is willing to do and talk about things most wives won’t. Being receptive to your ideas, playing with sex toys, dressing more sexy, working out, losing weight….
If you go out on date nights you might suggest going to a bar, club, or festival where there are available men, and women(?), and let her see how many might approach her. Of course you are nearby watching. Tell her she can be as flirty as she wants. Have a pre planned signal if she wants you to bail her out. Or text her during the night and she can tell them she is talking to the babysitter.
It could be fun for you both, it could be a confidence booster for her.
But as been shared here by others, slow and steady wins the race. You’ve planted the seed, it seems to be growing, and now you need to nuture it
Good luck and please continue to share your story.

[stillhopeful]

My wife is also nervous about oral, she's always worried it's not "clean enough". I will give her a licking occasionally, but I don't want to push it if it makes her uncomfortable.
As for anal, she has some tremendous orgasms with anal stimulation, but there is always that upbringing of it not being 'normal'. I've had the most luck slipping in a finger (make sure your nails are well trimmed and smooth!) when I feel she is in the right mood. She will on occasion ask for anal penetration, but it's a slow process.
Good luck! It sounds like you may be on your way.

[Baredare]

@BallSpanking true, it can be a slippery slope, but she always preferred real stuff to dildo. This time the difference was too big. I'm on the smaller side and she would still probably prefer the real one if it was bigger than me. Even if that is not the case pussy would go back to original size in a few days.

@mundyman
It would probably scare her because she never directly told she would like anything with another guy so I don't want to risk her closing back in her shell.

@stillhopeful
Thanks for sharing. Sounds like we are in the same boat, but mine is even more conservative.

[Baredare]

I have another update. After that monster dildo experience we had vanilla sex but it was different. It took us both longer to cum, because it was kinda just that, vanilla. Her pussy would probably need some time to return to her regular size, but we never gave her time to shrink. After vanilla sex she wated us to use "J" shaped vibrator where longer end goes in her pussy and shorter end is vibrating on her clitoris. We started switching between that "J" shaped and another one that attaches to the cock. It makes my cock feel bigger and her pussy tighter, but in reality it feels like it just makes her pussy wanting a bigger cock.

[Baredare]

I didn't post a update for a long time because short time after the last post my wife got offended. She said it sounded nasty when I talked about her dildos like they were her friends and it was annoying and disgousting. I told her I will stop and I did. For a few months things were more vanilla but I didn't complain.

As she continued with the gym she told me more and more of her friends commented how good she looked and she started getting more male attention. She told me delivery guy flirted with her, then she told me guys in gym are checking her out. One even started flirting with her. She started dressing to get more attention and she started using dildos more often while we were having sex. She was horny all the time.

Last week we were on the trip and across our room was a construction site. Curtains were wide open an workers could see us and our bedroom pretty well. She took a shower and walked in a bedroom just in her underwear for a few minutes not caring that they could see her like that. I wasn't used to see her act like that.

As I woke up in the morning first thing she did she kissed me and to my surprise she pushed her hand under the blanket and into my boxers. I was instantly hard. She told me to remove my boxers and as I did she started to play with my cock. I was even more surprised when she agreed to lower her panties and spread her legs.
Althought we were covered by blanked it was clear as day what we were doing. She turned her head towards me like she didn't want to know if the workers from the other side were looking, but I could see them. They were bussy with their own work.

She was moaning softly and was lifting her ass off the bed to press harder against my hand. As one of the workers saw us he stopped to take a better look. I stopped but my wife told me to continue. I couldn't believe this was happening. The guy tried not to stare but was turning more and more often too watch. Wife's moans became pretty loud and I couldn't hold it anymore. I shoot my cum all over the place and made a real mess.

My wife was well past caring and was rocking her hips up and down. I thought about telling her the guy was watching but I didn't. She came hard and her orgasm lasted as her body was shaking. The guy turned the other way just before she turned her head to see if someone was watching and put her panties back on.

I came three times since then thinking about it.

[Lucky Dog]

I didn't post a update for a long time because short time after the last post my wife got offended. She said it sounded nasty when I talked about her dildos like they were her friends and it was annoying and disgousting. I told her I will stop and I did. For a few months things were more vanilla but I didn't complain.

As she continued with the gym she told me more and more of her friends commented how good she looked and she started getting more male attention. She told me delivery guy flirted with her, then she told me guys in gym are checking her out. One even started flirting with her. She started dressing to get more attention and she started using dildos more often while we were having sex. She was horny all the time.

Last week we were on the trip and across our room was a construction site. Curtains were wide open an workers could see us and our bedroom pretty well. She took a shower and walked in a bedroom just in her underwear for a few minutes not caring that they could see her like that. I wasn't used to see her act like that.

As I woke up in the morning first thing she did she kissed me and to my surprise she pushed her hand under the blanket and into my boxers. I was instantly hard. She told me to remove my boxers and as I did she started to play with my cock. I was even more surprised when she agreed to lower her panties and spread her legs.
Althought we were covered by blanked it was clear as day what we were doing. She turned her head towards me like she didn't want to know if the workers from the other side were looking, but I could see them. They were bussy with their own work.

She was moaning softly and was lifting her ass off the bed to press harder against my hand. As one of the workers saw us he stopped to take a better look. I stopped but my wife told me to continue. I couldn't believe this was happening. The guy tried not to stare but was turning more and more often too watch. Wife's moans became pretty loud and I couldn't hold it anymore. I shoot my cum all over the place and made a real mess.

My wife was well past caring and was rocking her hips up and down. I thought about telling her the guy was watching but I didn't. She came hard and her orgasm lasted as her body was shaking. The guy turned the other way just before she turned her head to see if someone was watching and put her panties back on.

I came three times since then thinking about it.

Wow that's hot! good for you.

[BallSpanking]

Around here, that is called 'good progress'.

[Baredare]

I have a feeling she is willing to try other things, but only if they are not too direct. Unfortunately we have pretty busy life and that kind of situations are not that common. Looking back, maybe I could ask her to remove her shirt so worker could see her tits, but I am not sure if she would do it or act pissed.

[sharedfantasy]

That update gave me an instant hard-on, so I can only imagine the thrill you got when she exposed herself in undergarments, to other men, while in front of you…

… and the part where the construction worker watched you, while the two of you entertained him, is mind-blowing, especially as a wannabe

I understand events like that do not occur often, but if something like that were to ever happen again (voyeur-style), maybe you could encourage her to glance at the next guy, or better yet, lock eyes with him.

Regardless, that story is very hot and I’m very proud of the progress the two of you have made! Well done, brother

Can’t wait to read the next instalment.

[BallSpanking]

She appears to be turned on by the risk of being seen.

[Baredare]

She appears to be turned on by the risk of being seen.

You are probaby right. It's more about the risk of being seen then to actually doing it openly.