As you know my treasure passed away January 2021. I started to date about 3 months thereafter. I dated somewhere between 12-18 women in the next couple of months.
www.wifewantstoplay.com
But found two to be of particular interest, call the Big D & little D. Turns out Little D is very religious person and seems to have little interest in sex, and when she does is mainstream vanilla, which I sadly found out after we exchanged the "L" Big D has many of the same values as do I and isn't vanulla at all.
Little D is twice divorced with 3 grown children and 2 grandchildren. We met on Our Time & Match.com which is where I went when I re-entered the dating scene after decades. 1 son is very very successful who you see on TV all the time in ADs the other 2 are just above losers. Big D is widowed without children.
I mentioned to Little D about going to a sex club that myself and my treasure used to frequent, in a heartbeat she said absolutely not. When I posed the same thing to Big D her response was let me think about it a few days, with her final response being that we're not together long enough yet.
Little D is financially secure owns her own home, has money in the bank and an income. Big D on the other hand is Stone Cold broke, she doesn't have two nickels to rub together and lives in a rented room.
So I made a decision and continued with Little D.
Since we exchanged "L" we have been unspokenly exclusive, dinner every night occasional sexless 'sleepovers. Though I de-activated my profiles I still get matches and correspondence. When I can respond I do so telling them 'thanks but I'm off the market for now'. Disclaimer I'm a philanderer, I cheated on my 1st wife with my 2nd wife and cheated on my 2nd wife, my treasure, with many many men.
As of late when I get an interest from either of these dating sites I've been responding but added that I like to share. Most have no clue what I'm saying and when I clarify they're gone. It's kinda me playing knowing the outcome. Basically setting myself up for a refusal to go further. UNTIL. Several weeks ago one woman call her 'C' said that she'd be amenable to that and more. Over the next few weeks we discussed sex at length and in depth. She likes cock, likes anal, likes cum, has a fantasy to taste pussy, wants another 3-some (did one in her past), likes to watch men JO, wants to see 2 men together, likes video porn and reading erotica as well as listening to erotic audio books and toys. I asked her plainly how many men she had been with and very clearly she said she's stopped counting at 200.
We meet for the 1st time Sunday 6/25 while D was at church as we agreed to meet midday. As soon as I walked in her house I got one of the biggest kisses I have had in ages. We had a cup of tea and chatted, we talked about everything primarily about sex. As soon as we got off topic it was straight back to sex, if I didn't she did. For whatever reason at our first meeting we trusted each other explicitly and implicitly enough to tell each other things that we had never told the other people. After a cup of tea & chit chat we were in the sack for over 2 hours. She said she rarely orgasmed and I tried my best but failed ending in a mouth watering great blowjob that made my toes curl. she loved me going down on her and I loved her going down on me. By the way she's a widow of 7 years from a non-sexual marriage. She claimed it was great and didn't expect to cum as she rarely does. But thought it was sensational. Being the cuckold & compersion person I am I told her she needed to continue to date, we were on the same page, for whatever reason she felt we were a physical only thing.
There were several stumbling blocks that we discussed. I was in the somewhat exclusive relationship with Little D, this basically meant that I was now cheating. She had just hooked up with Chuck, who she was very interested in more than just a physical relationship who wanted her to be exclusive to him. I have ED issues she cannot orgasm.
On 6/28 she had a date with Chuck, she told me a few details. He gave great head and had magic fingers (similar to what she told me) but he made her cum and he came twice. She's currently in 7th heaven. Prior to their meeting she said she wasn't sure she could juggle more than one man at a time, and the he was dating material and I as sex material. It sounded like she found both in this guy. But we're still communicating on a sexual level leaving nothing out. I teased her and asked for picture not just the details. She said not this time but sent me a video form 2 year sago of her and another guy.
When I mentioned the sex club she said that sounds like fun. When I mentioned sharing the woman I care about again she said that sounds like fun. I reminded her of her new guy, Chuck, that wants her to be exclusive with him and she said she doesn't take that to mean exclusive of me. We've been Google chatting almost every morning talking sex, I send her videos and stills to get her feeling of them and every one she says it looks yummy, or something else positive.
So a few days later maybe July 1, we again met this time she advised me that she was with Chuck the night before. I told her repeatedly that since her relationship with Chuck may be beyond physical and also that I'm just physical that he comes first. She of course told me she appreciates that. The good thing is that the night before she said Chuck was so good that she had an orgasm with him I was so very happy and pleased for her.
I believe in compersion, basically her pleasure is my pleasure and her pleasure is more important than my pleasure. I brought some toys with me which made her ecstatic when she looked at them she got a smile for me to ear. What about 7-in flexible silicone vibrating dildo, a rabbit, a glass dildo and of course Hitachi Magic Wand, battery model not my plug in the wall model.
7/9 I spent time with C while Little D was at church. We had a marvelous time together I used the dildo on her and she actually squirted. It wasn't that I saw the wetness, I was down there with the dildo licking her and as soon as I moved my face away there was the squirt. I always dreamed of getting a facial like that and almost did, it was amazing to see. Telltale sign of an orgasm. Women can fake orgasms they can't fake squirting and squirting always accompanies an orgasm.
I went over after Little D & I parted and spent the night with her it was a wonderful night, in the morning she gave me a blowjob, but I just couldn't cum.
We've gotten into the habit of texting and then chatting in the morning she texting me that any morning I want I can come over for a blowjob. How can a guy refuse that kind of an offer.
Anyway July 13 she says Chuck is coming in the middle of the day that they're going to have some fun bedtime. That he had a hard stop when he had to leave That she hoping to get laid again from him. I wish her luck and then had an idea. I told her to text me when he leaves don't wipe up I'll be right over to clean her up. That's exactly what happened at 1:00 I got a text he just left that she's on the bed naked waiting for me. I hopped in the car and got over there I was there within 4 minutes. I walked in stripped as fast as I as I possibly could got on the bed and started to lick the creampie that he had left.
Things have progressed. We've had sex every few days. Though she said she can't orgasm. Each time we;re together I use a toy on her or my fingers and she has squirted. I don't ask if she had an orgasm, the squirt tells me everything I need to know. She had never heard about women that squirt nor had she experienced it.
A video of her with a friend 2 years ago.
View attachment Cheryl 4-2-21 converted.mp4
The SPAM of Viagra doesn't get me hard enough to get in her. Damn are we disappointed. Last week we went to the adult store located here in town. It was an eye opener for her this being her 1st visit. We selected a cock sleeve that we're gonna try, It won't be me in her but a covering over me and she's ok to try that. We looked at the strapon and she commented that she could use that to peg me, something I had expressed interest in.
Little D & I continue to not have sex. She went away for the weekend (7/13 - 7/17) with her offspring and I used that time to spoil C with a continuous weekend of sex, squirting and my cum. She was ecstatic. In our discussions she expressed an interest in adding a 3rd person, she wants to try a woman but is apprehensive about it but agreed to add a man. I found someone on Sniffies of all places and we had it scheduled for Tuesday 7/18 but a last minute biz trip canx that. She wasn't put off and still wants to do the MFM thing.
C went on a date (from OurTime) 7/15 with Scott. It turns out it was someone I know, so we had a predate discussion. She said it was planned to be a platonic date. I told her to be prepared "ya neva know", to not pass up the opportunity to get laid. She rethought it and made her bed & neatened up her bedroom, just in case, thanking me for the advice. Unfortunately it was platonic.
On 7/17 C had a midnight booty call from Chuck. She said it was good, real good. But he has developed some medical issues. Diagnosis was serious. She's not sure about the future with him. BUT she has feelings for him so he is her #1, I told her he is primary. He also has family issues that limit his time with her.
7/19 C had a brunch date with Dale, she met online. Based upon the texting she expected to have sex with him, but she said he made no movement towards that and she didn't feel any sexual energy. That her days of fucking just for fucking are behind her.
Little D spent the night here, no sex with her again.
7/20 Dale sent her dick pics telling her he had wanted to be in her so badly. She kinda told him he was a day late and a dollar short.
I surprised C and her lunch with her. We talk all the time and it always goes to sex. She says I reawakened her sexuality. But that I also spoiled her.
She showed me pics that Hugh sent her, a guy she had sex with a while ago that had gone silent. She had a chat about sex. Turns out he's bi like me and is into 3-some. We now have a 3-some setup for Thursday 7/27. She has a brunch & fuck date with him for Sunday 7/23. I told her if time works out let me know when he leaves and do cleanup. She said cleanup is a huge turn on for her.
A few weeks back I gave her some words to find the meaning of: cuckold, hotwife, compersion, wittol. She said it was an eye opener for her.
I also told her that I was like her cuckold. I encourage her to have sex with other men, that I want her to be sexually satisfied and I don't have a jealous bone in my body. The only thing that separates me from a real cuckold is that we're not married so technically the definition doesn't apply.
She had an updated waxing done on 7/20, landing strip for me. Told her that if time allows I'll help her get ready for her date.
7/21 C has a date with Dave today in Walterboro, then Bobby tomorrow 7/22 for lunch in Bluffton, then Hugh on Sunday 7/23, Robert a guy that claimed to be special forces maybe on Monday 7/24, then Hugh, C and me Thursday 7/27.
She felt Robert was a scammer so she dropped him from her growing stable.
This was the text she sent me after her time with Dave.
I'll keep you all posted as time goes by as I did with HWR.
Is this the start or the end (part 1)?
Thursday, 8/30, I asked my wife if Gayle is going to join us for dinner Friday 8/31. (we're going out for pizza and Gayle's husband Jack is away). She's engrossed in reading a book and without any thought blurts out, "no, Gayle has a date." Then she realizes what she just said, stops reading...
www.wifewantstoplay.com
But found two to be of particular interest, call the Big D & little D. Turns out Little D is very religious person and seems to have little interest in sex, and when she does is mainstream vanilla, which I sadly found out after we exchanged the "L" Big D has many of the same values as do I and isn't vanulla at all.
Little D is twice divorced with 3 grown children and 2 grandchildren. We met on Our Time & Match.com which is where I went when I re-entered the dating scene after decades. 1 son is very very successful who you see on TV all the time in ADs the other 2 are just above losers. Big D is widowed without children.
I mentioned to Little D about going to a sex club that myself and my treasure used to frequent, in a heartbeat she said absolutely not. When I posed the same thing to Big D her response was let me think about it a few days, with her final response being that we're not together long enough yet.
Little D is financially secure owns her own home, has money in the bank and an income. Big D on the other hand is Stone Cold broke, she doesn't have two nickels to rub together and lives in a rented room.
So I made a decision and continued with Little D.
Since we exchanged "L" we have been unspokenly exclusive, dinner every night occasional sexless 'sleepovers. Though I de-activated my profiles I still get matches and correspondence. When I can respond I do so telling them 'thanks but I'm off the market for now'. Disclaimer I'm a philanderer, I cheated on my 1st wife with my 2nd wife and cheated on my 2nd wife, my treasure, with many many men.
As of late when I get an interest from either of these dating sites I've been responding but added that I like to share. Most have no clue what I'm saying and when I clarify they're gone. It's kinda me playing knowing the outcome. Basically setting myself up for a refusal to go further. UNTIL. Several weeks ago one woman call her 'C' said that she'd be amenable to that and more. Over the next few weeks we discussed sex at length and in depth. She likes cock, likes anal, likes cum, has a fantasy to taste pussy, wants another 3-some (did one in her past), likes to watch men JO, wants to see 2 men together, likes video porn and reading erotica as well as listening to erotic audio books and toys. I asked her plainly how many men she had been with and very clearly she said she's stopped counting at 200.
We meet for the 1st time Sunday 6/25 while D was at church as we agreed to meet midday. As soon as I walked in her house I got one of the biggest kisses I have had in ages. We had a cup of tea and chatted, we talked about everything primarily about sex. As soon as we got off topic it was straight back to sex, if I didn't she did. For whatever reason at our first meeting we trusted each other explicitly and implicitly enough to tell each other things that we had never told the other people. After a cup of tea & chit chat we were in the sack for over 2 hours. She said she rarely orgasmed and I tried my best but failed ending in a mouth watering great blowjob that made my toes curl. she loved me going down on her and I loved her going down on me. By the way she's a widow of 7 years from a non-sexual marriage. She claimed it was great and didn't expect to cum as she rarely does. But thought it was sensational. Being the cuckold & compersion person I am I told her she needed to continue to date, we were on the same page, for whatever reason she felt we were a physical only thing.
There were several stumbling blocks that we discussed. I was in the somewhat exclusive relationship with Little D, this basically meant that I was now cheating. She had just hooked up with Chuck, who she was very interested in more than just a physical relationship who wanted her to be exclusive to him. I have ED issues she cannot orgasm.
On 6/28 she had a date with Chuck, she told me a few details. He gave great head and had magic fingers (similar to what she told me) but he made her cum and he came twice. She's currently in 7th heaven. Prior to their meeting she said she wasn't sure she could juggle more than one man at a time, and the he was dating material and I as sex material. It sounded like she found both in this guy. But we're still communicating on a sexual level leaving nothing out. I teased her and asked for picture not just the details. She said not this time but sent me a video form 2 year sago of her and another guy.
When I mentioned the sex club she said that sounds like fun. When I mentioned sharing the woman I care about again she said that sounds like fun. I reminded her of her new guy, Chuck, that wants her to be exclusive with him and she said she doesn't take that to mean exclusive of me. We've been Google chatting almost every morning talking sex, I send her videos and stills to get her feeling of them and every one she says it looks yummy, or something else positive.
So a few days later maybe July 1, we again met this time she advised me that she was with Chuck the night before. I told her repeatedly that since her relationship with Chuck may be beyond physical and also that I'm just physical that he comes first. She of course told me she appreciates that. The good thing is that the night before she said Chuck was so good that she had an orgasm with him I was so very happy and pleased for her.
I believe in compersion, basically her pleasure is my pleasure and her pleasure is more important than my pleasure. I brought some toys with me which made her ecstatic when she looked at them she got a smile for me to ear. What about 7-in flexible silicone vibrating dildo, a rabbit, a glass dildo and of course Hitachi Magic Wand, battery model not my plug in the wall model.
7/9 I spent time with C while Little D was at church. We had a marvelous time together I used the dildo on her and she actually squirted. It wasn't that I saw the wetness, I was down there with the dildo licking her and as soon as I moved my face away there was the squirt. I always dreamed of getting a facial like that and almost did, it was amazing to see. Telltale sign of an orgasm. Women can fake orgasms they can't fake squirting and squirting always accompanies an orgasm.
I went over after Little D & I parted and spent the night with her it was a wonderful night, in the morning she gave me a blowjob, but I just couldn't cum.
We've gotten into the habit of texting and then chatting in the morning she texting me that any morning I want I can come over for a blowjob. How can a guy refuse that kind of an offer.
Anyway July 13 she says Chuck is coming in the middle of the day that they're going to have some fun bedtime. That he had a hard stop when he had to leave That she hoping to get laid again from him. I wish her luck and then had an idea. I told her to text me when he leaves don't wipe up I'll be right over to clean her up. That's exactly what happened at 1:00 I got a text he just left that she's on the bed naked waiting for me. I hopped in the car and got over there I was there within 4 minutes. I walked in stripped as fast as I as I possibly could got on the bed and started to lick the creampie that he had left.
Things have progressed. We've had sex every few days. Though she said she can't orgasm. Each time we;re together I use a toy on her or my fingers and she has squirted. I don't ask if she had an orgasm, the squirt tells me everything I need to know. She had never heard about women that squirt nor had she experienced it.
A video of her with a friend 2 years ago.
View attachment Cheryl 4-2-21 converted.mp4
The SPAM of Viagra doesn't get me hard enough to get in her. Damn are we disappointed. Last week we went to the adult store located here in town. It was an eye opener for her this being her 1st visit. We selected a cock sleeve that we're gonna try, It won't be me in her but a covering over me and she's ok to try that. We looked at the strapon and she commented that she could use that to peg me, something I had expressed interest in.
Little D & I continue to not have sex. She went away for the weekend (7/13 - 7/17) with her offspring and I used that time to spoil C with a continuous weekend of sex, squirting and my cum. She was ecstatic. In our discussions she expressed an interest in adding a 3rd person, she wants to try a woman but is apprehensive about it but agreed to add a man. I found someone on Sniffies of all places and we had it scheduled for Tuesday 7/18 but a last minute biz trip canx that. She wasn't put off and still wants to do the MFM thing.
C went on a date (from OurTime) 7/15 with Scott. It turns out it was someone I know, so we had a predate discussion. She said it was planned to be a platonic date. I told her to be prepared "ya neva know", to not pass up the opportunity to get laid. She rethought it and made her bed & neatened up her bedroom, just in case, thanking me for the advice. Unfortunately it was platonic.
On 7/17 C had a midnight booty call from Chuck. She said it was good, real good. But he has developed some medical issues. Diagnosis was serious. She's not sure about the future with him. BUT she has feelings for him so he is her #1, I told her he is primary. He also has family issues that limit his time with her.
7/19 C had a brunch date with Dale, she met online. Based upon the texting she expected to have sex with him, but she said he made no movement towards that and she didn't feel any sexual energy. That her days of fucking just for fucking are behind her.
Little D spent the night here, no sex with her again.
7/20 Dale sent her dick pics telling her he had wanted to be in her so badly. She kinda told him he was a day late and a dollar short.
I surprised C and her lunch with her. We talk all the time and it always goes to sex. She says I reawakened her sexuality. But that I also spoiled her.
She showed me pics that Hugh sent her, a guy she had sex with a while ago that had gone silent. She had a chat about sex. Turns out he's bi like me and is into 3-some. We now have a 3-some setup for Thursday 7/27. She has a brunch & fuck date with him for Sunday 7/23. I told her if time works out let me know when he leaves and do cleanup. She said cleanup is a huge turn on for her.
A few weeks back I gave her some words to find the meaning of: cuckold, hotwife, compersion, wittol. She said it was an eye opener for her.
I also told her that I was like her cuckold. I encourage her to have sex with other men, that I want her to be sexually satisfied and I don't have a jealous bone in my body. The only thing that separates me from a real cuckold is that we're not married so technically the definition doesn't apply.
She had an updated waxing done on 7/20, landing strip for me. Told her that if time allows I'll help her get ready for her date.
7/21 C has a date with Dave today in Walterboro, then Bobby tomorrow 7/22 for lunch in Bluffton, then Hugh on Sunday 7/23, Robert a guy that claimed to be special forces maybe on Monday 7/24, then Hugh, C and me Thursday 7/27.
She felt Robert was a scammer so she dropped him from her growing stable.
This was the text she sent me after her time with Dave.
I'll keep you all posted as time goes by as I did with HWR.
