The Initiation of Sherry
- 3 years ago
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Shopping Trips With Sherry free porn video
Slowly, Sherry and I begin to become more than just friends. Sex is off limits because neither of us want the possibility of a child, STD's, etc. She has no problem visiting me and I am still getting used to her place. Hardly anyone shows up at my house unannounced, while a few of her pals still drop in when they feel like it or if they are invited. Sherry or one of her bitches will ask me which panty I have on and I reply with the correct information, causing much laughter. I am more than willing to prove it to them, even if it does shock the hell out of them.
My panty collection has grown, as has other clothing that Sherry and a few close friends have picked out for me. When I model my new clothes, I remind them that it must stay between us. Her friends have seen me naked in a corner, though nobody has seen Mommy Sherry punish me beforehand. We agree to keep those private moments between us, regardless how often she teases that she might let others in on it. We do agree that sooner or later someone will walk in on her doing this. It's just a matter of time. The thought makes us both laugh and wonder who feels more aroused at the idea. While I hate thinking about it, it will happen soon enough.
The two of us like to shop together and have a fun time. During one weekend we decide to go to some small stores. She tells me that a friend has a clothing store and does good work. As she drives, I notice that her friend is within a reasonable distance and the shop is in a good neighborhood. As we pull in, I notice that it is a normal home that was turned into a store. The sign lists which hours it is open and we are showing up towards the end of the day. As we enter, a few women are talking at the counter. We introduce each other and are greeted by the store owner, Sandy. She is in her mid- to late-twenties and of fair build. It is almost closing time, but that didn't seem to matter.
"You caught me just in time," Sandy says.
Sherry explains that she would like to get some slacks and that she wanted to see if she could measure me up, as well.
"I'd be most delighted," Sandy says with a sweet smile.
After switching the sign to "Closed" and locking the door, the three of us go to the sewing area in the rear of the establishment and get started. I notice a few windows and upon inspection decide that all is fine. With the door closed to the room, I go behind a partition, undress and return wearing only a male G-string in pink satin. Sandy smiles and gives me a whistle or two as I turn around to show off my toned physique.
"Now, David," Sandy comments, "let's get you sized up. I like the item you are wearing."
"Doesn't Davey look lovely?" Sherry comments. "He likes to wear cute little things like this."
After awhile, Sandy has all the numbers she needs and jots them down in her book, writing "Davey" above them. She taps my buns with her ruler and I blush a bit, prompting a wink. Sherry then goes for her purse and returns.
"We aren't quite finished yet, Davey."
I am still thong-clad and walk behind the partition with Sherry. Sherry tucks me inside, checks to see if I have shaved all my pussy hair, secures the bandage and applies extra tape. We walk out and I stand in front of Sandy.
"Oh, my!" is all she can say as she stares at my clean-shaven clitty. Sherry says that I can be seen like this while here, but that we need to be quite discrete. I am then led over a chair as Sherry collects her purse. With ease, she removes two paddles from it and walks over next to me.
"Now, you may use this one if you so choose. Davey is a naughty girl and needs to be kept in line."
Sandy picks up the thicker paddle and blushes. With some prompting, she sits down and I go across her lap. Five solid whacks per cheek with it, followed by five slaps per cheek with her bare hand and a quick swat with the smaller paddle.
I stand up and watch as she is asked to sign the larger paddle she used on my toned ass. Sherry asks what she wishes to be called and I am asked to sign the smaller one for her. I do so, adding a small heart and hand it back, asking her to read it.
"To Sandy, From Davey"
"Now, Davey, please follow me," Sandy comments. She leads me to a corner next to a small window. Sherry tells her that I need to remain there a bare minimum of fifteen minutes, prompting a laugh. The two of them go about their business and write up an order for both Sherry and I. When my time is up, I am asked to face them. Sherry removes the tape and bandage, allowing my penis to come out and slowly return to normal. I feel ashamed as I stand in front of her with my manhood slowly becoming rock hard. Sandy comments on how my pussy is nice and clean, making me blush.
"Now, Davey, what do you say to this nice lady?"
"Thank you, Mommy Sandy."
Sandy blushes and smiles.
"My, my. Noone has ever called me that before. You may just call me Mommy and I'll call you Davey," she comments.
"If you feel needs to be spanked or paddled in the future, you may do so. Corner time is a must. Also," Sherry adds, "should someone happen to notice our baby boy in his corner, so be it."
Sandy laughs and comments that all naughty boys need kept in tow, also noticing that a few have added their name to the larger paddle. I am then asked to get dressed. Sherry has replaced my pink thong with one in a floral print and asks me to model it before putting on my jeans, causing more laughs. Sandy comments that with the numbers she has that she could make all of my clothing, including underwear. I blush as Sherry tells her any underthings she might make are all called panties. I review the order Sherry wrote up for me, add my own choices to it and pay the bill.
"I'll call both of you when everything is finished."
A few weeks later, we get a call that our clothing orders are ready to be picked up. We visit the store together and pick up our things. We then go to the second floor and I am asked to model my new items. I first inspect the windows and notice that if someone is standing at just the right spot that I could be seen. I laugh at the idea and go about stripping for them, not really worrying about it. As requested, there are two pair of slacks, as well as three pair of jeans. On her own, or maybe Sherry's request, I also find a packet containing panties and a few thongs. They are from my own collection, thankfully, since I see the name brand and such on them. I model each item, slacks with panties and jeans with a thong beneath. The house is secluded and I feel okay. They have a smoother fit and I compliment her on her work. Once naked, Sandy is asked if I deserve any punishment and corner time.
"Oh, perhaps a little of both."
Sandy swats me five times per cheek with her new paddle, which I count out for her. I am also given a few well-placed slaps on my bare ass with her firm hand. No pain, but merely symbolic. She pats my bare behind as I am led to a different corner, which appears to be a bit more open. I am to stand there for twenty minutes before being allowed to leave and get dressed. As fate would have it, a lady rings the doorbell just as I am getting dressed. Sherry goes down, answers the door and eagerly brings the lady up with her. Sandy giggles and comments that we missed our chance.
"Too bad," Sandy comments. "I think it would have been sweet for her to see you. I knew I should have made you stand there for thirty minutes, Davey. Maybe next time."
The female customer looks at me and shakes her head. Some women just can't take a good joke.
As we are leaving, Sherry thanks her and asked if she liked the peep show.
"Yes," she replies. "I think Davey would make a good clothing model and a sexy stripper."
I turn around and she blushes as I respond.
"As long as you and your female friends can behave and are at least 21, give me a call."
"I will," Sandy replies as she taps my behind with her paddle. "I'm sure you would look lovely and do well. My friends tip well, Davey."
"Also, if our Davey needs corner time during a show," Sherry adds, "please see to it. Fifteen minutes, but more if he is naughty."
"Yes, I agree." Sandy replies. "As for we what talked about, anytime you wish."
As we leave, I ask Sherry what she was talking about.
"Oh, just you never mind," she replies with a sly grin as we drive to her place.
As I prepare to stay for the weekend, I put my stuff in the spare bedroom. Sherry is getting stuff ready and a friend shows up. Then another and after awhile a few more. I am uncomfortable and curious. One of them has a package and hands it to me.
"This is from all of us, honey."
I look over at Sherry and she reminds me that if I open anything that I must show it off. I check the card and it has been signed by what seems to be everyone in attendance. I open it and find a pair of slacks, a pair of jeans and an even smaller package. I open it and glare at the group. I start laughing and make a comment.
"What?! You're all crazy!"
The box contains several panties, including thongs in a variety of colors and prints. I notice these are new, but remind myself that I already have some like these styles.
"Well," one of them comments, "let's have a look at them. Don't be shy."
I remind them that what happens there stays at Sherry's and they all agree. Making sure that the window blinds are closed, I go behind a fold-out partition and return wearing a new pair of pink satin panties. The fit is just right. I am asked to check the tag. "Sandy's" is on it, making me laugh a bit.
With only a little coaxing, I decide to go with the flow and model the slacks and jeans, gaining whistles as I put the slacks on in front of them in my new panties. After a break, I go about modeling a new thongs and then the jeans. I am then asked to model pantyhose and stockings, which were in another box that was kept until later. The hosiery and stockings fit well. Sherry and a friend come over and measure my waist and from the top of the stockings to the waist. As I model the final item, one of them tempts me to simply remove it and be seen in the nude to be spanked. Sherry smiles as I defy them by putting on a thong, saying I want my penis protected.
"That's okay, girls," Sherry calmly says. "We can still spank him naked later. That piece of dental floss is out of the way."
I am spanked by each woman on my near-bare buns. Each is allowed five swats with the middleweight paddle, five slaps per cheek with their open hand and one with a lightweight paddle. After each finish, I stand up and wait for them to sign the paddle. I sign the smaller one and call each one Mommy and the cycle repeats. I am in severe distress when Sallie finishes. The only thing bruised is my ego, since they were all told to be ''fair, yet firm'' on my little ass.. I then put my thong in the hamper and am walked to the corner totally naked by Sherry, causing much laughter and whistles.
It is dark outside, but the moon is out and shines on my sore behind. I stand there for what seems like an eternity as the ladies comment on just how cute I look. Someone could see me from outside, but I don't care. A few comment on how many signatures are on the paddle and are told by Sherry that they can bring their own along for any future showings. Once my time is up, I am ordered to turn around with my hands above my head.
"Show them your little wee-wee, darling. Don't be shy," Sherry says, adding "I'm sure they've seen smaller ones."
My penis is still small when they see it and laugh. I slowly become hard and watch as several put money into the tip jar and comment that I was a good sport and that the show was well worth it. My penis has returned to its normal size as I put on a thong and jeans as they prepare to leave. Sandy is not present for this modeling session, but part of me is quite sure that I will do shows for her to model her works.
"You hussies tricked me," I comment, prompting giggles.
"Well, Davey," Sherry replies, "they liked what they saw."
Everyone laughs as she smiles and mentions that there may be more shows in my future. They can tell I am serious when I say that any future shows must be tame and that we need to set an age limit range. I point out that there would be legal issues if a minor sees my total package and that little old ladies might not be able to take it. The range of the women at this show was from mid-twenties to early fifties. One pair even said they were mother and daughter, making me blush.
After the last one leaves, Sherry locks the door, walks over to her purse and brings out her own paddle.
"I didn't show them this, but was tempted. I should have tucked your wee-wee inside, as well."
I respond in a calm manner.
"Well, let's keep that stuff between us."
Sherry then tries to tell me what she might want to buy for me. I simply tell her to be sensible. I then walk back to my room and get my own lightweight paddle.
"My turn, you little tramp."
Sherry laughs as she lowers her jeans and I give her a paddling and spanking while over my lap. I then lead her to a corner that is just for her. Nobody but I can see her, but I tease that I could move her to a more open space and strip naked.
"Now be a good slut and stay in your own corner until Daddy feels you've learned your lesson."
I use the restroom and come out ten minutes later. I pat her naked ass and tell her that her sentence is up. I pinch her little tush a good one, causing her to wriggle and squirm. I slap her ass and tell her she better behave from now on, prompting laughs from both of us. We watch the news and turn in for the night.
During each day of my stay, I get plenty of discipline and corner time from Sherry. A few friends stop by and I model for them. Each goes thru the same routine with the paddles, spanking and corner time. Sherry has a ready supply of lightweight paddles for each new Mommy, while some had me also sign ones they brought along and used on me.
One day, the two of go to the spare room and she shows me a few hospital items an aunt of hers had. The inventory includes potty chairs used by older patients when she worked as a private-duty nurse.. One is very tight and pinches my ass, making her giggle. She puts them back into the closet and we have lunch. I am reminded that she wants to make that room mine for when she decides I need to remain there for an extended stay. Part of me is curious as to what that might entail.
As I leave at the end of the weekend, we joke of what might happen later on. She tells me she will give Sandy the new measurement to add to my profile. I add money to our own jar for any future purchases, as well as the one to help pay for any future items that she and her hussies might buy. My numbers were no doubt shared with several of them, as well.
I know damn well Sherry was all horny when I left and I was, too. While calling someone my own age or older Mommy, the thought of telling a college-age female that arouses me. I stroke my shaft and explode like fireworks on the Fourth of July!
My panty collection has grown, as has other clothing that Sherry and a few close friends have picked out for me. When I model my new clothes, I remind them that it must stay between us. Her friends have seen me naked in a corner, though nobody has seen Mommy Sherry punish me beforehand. We agree to keep those private moments between us, regardless how often she teases that she might let others in on it. We do agree that sooner or later someone will walk in on her doing this. It's just a matter of time. The thought makes us both laugh and wonder who feels more aroused at the idea. While I hate thinking about it, it will happen soon enough.
The two of us like to shop together and have a fun time. During one weekend we decide to go to some small stores. She tells me that a friend has a clothing store and does good work. As she drives, I notice that her friend is within a reasonable distance and the shop is in a good neighborhood. As we pull in, I notice that it is a normal home that was turned into a store. The sign lists which hours it is open and we are showing up towards the end of the day. As we enter, a few women are talking at the counter. We introduce each other and are greeted by the store owner, Sandy. She is in her mid- to late-twenties and of fair build. It is almost closing time, but that didn't seem to matter.
"You caught me just in time," Sandy says.
Sherry explains that she would like to get some slacks and that she wanted to see if she could measure me up, as well.
"I'd be most delighted," Sandy says with a sweet smile.
After switching the sign to "Closed" and locking the door, the three of us go to the sewing area in the rear of the establishment and get started. I notice a few windows and upon inspection decide that all is fine. With the door closed to the room, I go behind a partition, undress and return wearing only a male G-string in pink satin. Sandy smiles and gives me a whistle or two as I turn around to show off my toned physique.
"Now, David," Sandy comments, "let's get you sized up. I like the item you are wearing."
"Doesn't Davey look lovely?" Sherry comments. "He likes to wear cute little things like this."
After awhile, Sandy has all the numbers she needs and jots them down in her book, writing "Davey" above them. She taps my buns with her ruler and I blush a bit, prompting a wink. Sherry then goes for her purse and returns.
"We aren't quite finished yet, Davey."
I am still thong-clad and walk behind the partition with Sherry. Sherry tucks me inside, checks to see if I have shaved all my pussy hair, secures the bandage and applies extra tape. We walk out and I stand in front of Sandy.
"Oh, my!" is all she can say as she stares at my clean-shaven clitty. Sherry says that I can be seen like this while here, but that we need to be quite discrete. I am then led over a chair as Sherry collects her purse. With ease, she removes two paddles from it and walks over next to me.
"Now, you may use this one if you so choose. Davey is a naughty girl and needs to be kept in line."
Sandy picks up the thicker paddle and blushes. With some prompting, she sits down and I go across her lap. Five solid whacks per cheek with it, followed by five slaps per cheek with her bare hand and a quick swat with the smaller paddle.
I stand up and watch as she is asked to sign the larger paddle she used on my toned ass. Sherry asks what she wishes to be called and I am asked to sign the smaller one for her. I do so, adding a small heart and hand it back, asking her to read it.
"To Sandy, From Davey"
"Now, Davey, please follow me," Sandy comments. She leads me to a corner next to a small window. Sherry tells her that I need to remain there a bare minimum of fifteen minutes, prompting a laugh. The two of them go about their business and write up an order for both Sherry and I. When my time is up, I am asked to face them. Sherry removes the tape and bandage, allowing my penis to come out and slowly return to normal. I feel ashamed as I stand in front of her with my manhood slowly becoming rock hard. Sandy comments on how my pussy is nice and clean, making me blush.
"Now, Davey, what do you say to this nice lady?"
"Thank you, Mommy Sandy."
Sandy blushes and smiles.
"My, my. Noone has ever called me that before. You may just call me Mommy and I'll call you Davey," she comments.
"If you feel needs to be spanked or paddled in the future, you may do so. Corner time is a must. Also," Sherry adds, "should someone happen to notice our baby boy in his corner, so be it."
Sandy laughs and comments that all naughty boys need kept in tow, also noticing that a few have added their name to the larger paddle. I am then asked to get dressed. Sherry has replaced my pink thong with one in a floral print and asks me to model it before putting on my jeans, causing more laughs. Sandy comments that with the numbers she has that she could make all of my clothing, including underwear. I blush as Sherry tells her any underthings she might make are all called panties. I review the order Sherry wrote up for me, add my own choices to it and pay the bill.
"I'll call both of you when everything is finished."
A few weeks later, we get a call that our clothing orders are ready to be picked up. We visit the store together and pick up our things. We then go to the second floor and I am asked to model my new items. I first inspect the windows and notice that if someone is standing at just the right spot that I could be seen. I laugh at the idea and go about stripping for them, not really worrying about it. As requested, there are two pair of slacks, as well as three pair of jeans. On her own, or maybe Sherry's request, I also find a packet containing panties and a few thongs. They are from my own collection, thankfully, since I see the name brand and such on them. I model each item, slacks with panties and jeans with a thong beneath. The house is secluded and I feel okay. They have a smoother fit and I compliment her on her work. Once naked, Sandy is asked if I deserve any punishment and corner time.
"Oh, perhaps a little of both."
Sandy swats me five times per cheek with her new paddle, which I count out for her. I am also given a few well-placed slaps on my bare ass with her firm hand. No pain, but merely symbolic. She pats my bare behind as I am led to a different corner, which appears to be a bit more open. I am to stand there for twenty minutes before being allowed to leave and get dressed. As fate would have it, a lady rings the doorbell just as I am getting dressed. Sherry goes down, answers the door and eagerly brings the lady up with her. Sandy giggles and comments that we missed our chance.
"Too bad," Sandy comments. "I think it would have been sweet for her to see you. I knew I should have made you stand there for thirty minutes, Davey. Maybe next time."
The female customer looks at me and shakes her head. Some women just can't take a good joke.
As we are leaving, Sherry thanks her and asked if she liked the peep show.
"Yes," she replies. "I think Davey would make a good clothing model and a sexy stripper."
I turn around and she blushes as I respond.
"As long as you and your female friends can behave and are at least 21, give me a call."
"I will," Sandy replies as she taps my behind with her paddle. "I'm sure you would look lovely and do well. My friends tip well, Davey."
"Also, if our Davey needs corner time during a show," Sherry adds, "please see to it. Fifteen minutes, but more if he is naughty."
"Yes, I agree." Sandy replies. "As for we what talked about, anytime you wish."
As we leave, I ask Sherry what she was talking about.
"Oh, just you never mind," she replies with a sly grin as we drive to her place.
As I prepare to stay for the weekend, I put my stuff in the spare bedroom. Sherry is getting stuff ready and a friend shows up. Then another and after awhile a few more. I am uncomfortable and curious. One of them has a package and hands it to me.
"This is from all of us, honey."
I look over at Sherry and she reminds me that if I open anything that I must show it off. I check the card and it has been signed by what seems to be everyone in attendance. I open it and find a pair of slacks, a pair of jeans and an even smaller package. I open it and glare at the group. I start laughing and make a comment.
"What?! You're all crazy!"
The box contains several panties, including thongs in a variety of colors and prints. I notice these are new, but remind myself that I already have some like these styles.
"Well," one of them comments, "let's have a look at them. Don't be shy."
I remind them that what happens there stays at Sherry's and they all agree. Making sure that the window blinds are closed, I go behind a fold-out partition and return wearing a new pair of pink satin panties. The fit is just right. I am asked to check the tag. "Sandy's" is on it, making me laugh a bit.
With only a little coaxing, I decide to go with the flow and model the slacks and jeans, gaining whistles as I put the slacks on in front of them in my new panties. After a break, I go about modeling a new thongs and then the jeans. I am then asked to model pantyhose and stockings, which were in another box that was kept until later. The hosiery and stockings fit well. Sherry and a friend come over and measure my waist and from the top of the stockings to the waist. As I model the final item, one of them tempts me to simply remove it and be seen in the nude to be spanked. Sherry smiles as I defy them by putting on a thong, saying I want my penis protected.
"That's okay, girls," Sherry calmly says. "We can still spank him naked later. That piece of dental floss is out of the way."
I am spanked by each woman on my near-bare buns. Each is allowed five swats with the middleweight paddle, five slaps per cheek with their open hand and one with a lightweight paddle. After each finish, I stand up and wait for them to sign the paddle. I sign the smaller one and call each one Mommy and the cycle repeats. I am in severe distress when Sallie finishes. The only thing bruised is my ego, since they were all told to be ''fair, yet firm'' on my little ass.. I then put my thong in the hamper and am walked to the corner totally naked by Sherry, causing much laughter and whistles.
It is dark outside, but the moon is out and shines on my sore behind. I stand there for what seems like an eternity as the ladies comment on just how cute I look. Someone could see me from outside, but I don't care. A few comment on how many signatures are on the paddle and are told by Sherry that they can bring their own along for any future showings. Once my time is up, I am ordered to turn around with my hands above my head.
"Show them your little wee-wee, darling. Don't be shy," Sherry says, adding "I'm sure they've seen smaller ones."
My penis is still small when they see it and laugh. I slowly become hard and watch as several put money into the tip jar and comment that I was a good sport and that the show was well worth it. My penis has returned to its normal size as I put on a thong and jeans as they prepare to leave. Sandy is not present for this modeling session, but part of me is quite sure that I will do shows for her to model her works.
"You hussies tricked me," I comment, prompting giggles.
"Well, Davey," Sherry replies, "they liked what they saw."
Everyone laughs as she smiles and mentions that there may be more shows in my future. They can tell I am serious when I say that any future shows must be tame and that we need to set an age limit range. I point out that there would be legal issues if a minor sees my total package and that little old ladies might not be able to take it. The range of the women at this show was from mid-twenties to early fifties. One pair even said they were mother and daughter, making me blush.
After the last one leaves, Sherry locks the door, walks over to her purse and brings out her own paddle.
"I didn't show them this, but was tempted. I should have tucked your wee-wee inside, as well."
I respond in a calm manner.
"Well, let's keep that stuff between us."
Sherry then tries to tell me what she might want to buy for me. I simply tell her to be sensible. I then walk back to my room and get my own lightweight paddle.
"My turn, you little tramp."
Sherry laughs as she lowers her jeans and I give her a paddling and spanking while over my lap. I then lead her to a corner that is just for her. Nobody but I can see her, but I tease that I could move her to a more open space and strip naked.
"Now be a good slut and stay in your own corner until Daddy feels you've learned your lesson."
I use the restroom and come out ten minutes later. I pat her naked ass and tell her that her sentence is up. I pinch her little tush a good one, causing her to wriggle and squirm. I slap her ass and tell her she better behave from now on, prompting laughs from both of us. We watch the news and turn in for the night.
During each day of my stay, I get plenty of discipline and corner time from Sherry. A few friends stop by and I model for them. Each goes thru the same routine with the paddles, spanking and corner time. Sherry has a ready supply of lightweight paddles for each new Mommy, while some had me also sign ones they brought along and used on me.
One day, the two of go to the spare room and she shows me a few hospital items an aunt of hers had. The inventory includes potty chairs used by older patients when she worked as a private-duty nurse.. One is very tight and pinches my ass, making her giggle. She puts them back into the closet and we have lunch. I am reminded that she wants to make that room mine for when she decides I need to remain there for an extended stay. Part of me is curious as to what that might entail.
As I leave at the end of the weekend, we joke of what might happen later on. She tells me she will give Sandy the new measurement to add to my profile. I add money to our own jar for any future purchases, as well as the one to help pay for any future items that she and her hussies might buy. My numbers were no doubt shared with several of them, as well.
I know damn well Sherry was all horny when I left and I was, too. While calling someone my own age or older Mommy, the thought of telling a college-age female that arouses me. I stroke my shaft and explode like fireworks on the Fourth of July!
Lauryn
- 09.03.2021
- 50
- 0
- Category:
- Humor
