Alice's Mother Helps Out

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Helping my girlfriend's mother tailor a dress.
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Classmate Alice and I had been dating for several months and she had me wearing lingerie constantly for her. I was loving it and regretted only those school days where I had a gym class and had to wear jockey shorts. However, we were 18 and ready to graduate which made me realize gym days were now few in number. Our relationship was now more open, in that she sometimes accepted a date with another guy but I knew I was still her main squeeze. She'd turn me on by telling me all about what she and her date would do to each other.

Spring had arrived and I found myself adoring the change in garments for the girls and women. Alice had given me flower patterned full skirt as a present to wear after Memorial Day. Until then, though, I could wear it inside her house as I was still living at home. I was soon to learn I'd be wearing it to a party at their cottage.

Little did I know Alice kept no secrets from her widowed mother. They talked about everything and she was up to date on all the escapades the two of us enjoyed together. She even knew my preference to wear pink lingerie and that Alice had introduced me to wearing a garter belt.

One Thursday afternoon, having stopped by Alice's house, she mentioned to her mother that I could help her with her dress hem. This meant little to me because I knew nothing about how to fix hemlines.

Kathleen, Alice's mom, was quite a seamstress who took pride in her creations. She had made a lot of clothing for herself, friends, and each of the three girls. Then they broached the question to me that they had already planned.

"Eric," Alice said, "Mom needs some help in getting the hemline of the formal she is making to wear to the country club "Spring Fling" in a couple of weeks. It's a full skirted affair with a tulle overlay and I'm too short to be of any help on this but you're her height."

It didn't occur to me that Alice could have stood on some books and achieved the same result as a taller mannequin. I was being set up didn't know it.

"Would you mind just slipping on a dress she's doing so she can set the hemline to the proper length and make it level?" she went on. "She has a low step box in front of a tri-fold tailor's mirror in the bedroom for this."

"I guess I could," I replied a bit nervously and a bit in shock at such a request. "Do you want me to do it now?" I inquired assuming I'd just pull it on over my clothes.

"No, dear," Kathleen broke in, "We'll find another time more convenient." I was relieved as it could be embarrassing to put on a dress in front of Alice's mom.

We had planned to go to a Saturday afternoon movie and Alice told me to put my car in the park down the hill from her house and come in to the garage through the back door and into the house that way. Mysterious, but we'd done it this way before so I didn't give it much thought. Maybe she planned to drive?

At Alice's direction I'd worn a pair of sheer pink nylon brief style panties with chiffon edging along the leg openings and waistband over my lacey pink garter belt and a pair of dark cinnamon colored RHT nylon stockings. Just feeling myself sliding around inside my lingerie had me turned on and I was eager to get to the movies as I knew Alice and I would be feeling each other up.

Entering the house through the garage I noticed their big black Cadillac was not there. Was I to drive after all? Calling out, as I entered, her mom answered me.

"Come on in," she said, "I've got everything all set up for taking the measurements and getting the hemline pinned properly. I wore what I have on because I'll need to put the dress on once we've pinned the hem so I can make sure it hangs right on me. I greatly appreciate your help on this."

Momentarily stunned, I managed to stammer, "Where's Alice? We are planning to see that new Disney movie downtown this afternoon."

"Oh," Kathleen smiled, "We decided it was more of a kids' movie and so she took her sisters to see it. It will give us a chance to take care of that dress hem without the younger girls around."

Although disappointed, I let her lead me through the house toward where I'd need to slip the dress over myself. As she led me back to the master bedroom, I got a nice view from behind her and realized she had on little under that robe.

She really was a beautiful woman.

Kathleen got the dress out of the closet and showed it to me. It was a soft baby blue color of satin with a strapless top that was fairly tight fitting. Evidently, it was for someone going to a fine dinner or dance.

"That's beautiful," I gushed as she showed off the dress to me. I was actually envious and wished I had such a dress to wear and dance with a guy.

Unzipping the back she showed me the inside of the gown which meant one would not wear a bra with it since she'd sewn cups inside it to hold her breasts up nicely and show off some cleavage.

Kathleen brought out a pair of her high heels for me to slip on "to make sure the height was the same as hers for pinning the hem" and asked me to try them on. I knew they'd fit as I'd worn them before.

Now I had a problem! I couldn't slip off my loafers and socks without her seeing I was wearing nylon stockings!! What was I going to do?!

Kathleen sensed my dilemma and gave me a knowing smile, "It's okay. Alice and I keep no secrets from each other. Why do you think I started her on birth control pills? She's also confided you prefer wearing women's lingerie to men's yucky underwear. She also told me what she wanted you to wear today, so I know what you have on under your shirt and slacks. I'll bet you look darling," she said.

I was mortified and blushing a beet red at her comments.

"Come on, dear, we need to get started or we won't get this dress finished. Off with your outer things and we'll get a bra to put on you so the top won't sag."

I had no choice and she began helping me out of my things. I was both turned on and scared. What bothered me most was that she'd see my rising "clitty" inside my sheer panties.

Soon enough I was standing before my girlfriend's mother wearing just my nylons and garter belt and the ultra-sheer pink panties.

"I can see why Alice says you look so cute dressed this way. I think you look adorable," she added as she picked up one of her pink bras and fetched a pair of her high heels for me to slip into.

She put the bra on me as I tried to hide my hard-on, and she smirked at my fears. "Just don't worry about what's going on inside your panties, Dear," she said. "I understand and it is normal to react like that."

With the pink satin bra fitted on me she stuffed it with some of her nylon panties and adjusted the cups until satisfied with the fit and look. Then she had me step into a pair of her black patent leather high slingback high heels with 4 inch spikes.

She seemed pleased we were the same shoe size in women's things and then began to frown. "Hmmm," she mused, "I think we have a bit of a problem."

I couldn't imagine what it was and then she went on, "Your waist is bigger than we want for the dress. If you don't mind, I'll need to put one of my old waist cinchers on you so you can fit inside the tightness of the waist area."

Nonetheless, I was still mortified. An 18 year old boy standing before a 37 year old grown woman dressed in lingerie. However, she turned her back to me and began getting the waist cincher to put on me and then, pausing as if to reflect for a moment, before surprising me with some large slim foam pads.

"You hips are too boyish, she told me, so I want to just slip these inside your panties to give you a more feminine silhouette."

I was too amazed to think of what to say and before I knew it she was fitting the foam padding inside my panties.

My cockette was not cooperating and was standing out straight despite my attempts to hide it between my legs. My knee caps were bouncing up and down inside the nylons covering my limbs and Kathleen laughed.

"Do we really need to do all this?" I asked nervously.

"Of course, dear," Kathleen responded as she handed me a taffeta half slip, "We've got to get the dress to hang properly or all will be for naught.

"Alice told me how you love dressing like a girl but I didn't think I'd get to witness it. You look too sweet. Just don't get too excited and have an 'accident' in your panties," she muttered as she picked up the dress and helped me step inside.

I was unprepared for the sensations of my nylons sliding against the taffeta half-slip inside the satin dress. I knew I'd soon burst if these sensations kept up. Even the garter straps were teasing me as they slid back and forth across my hips as I moved about while the nylons tugged delightfully on the garter tabs.

"Are you okay, Eric?" she asked as she saw me standing there trembling.

"Y-yes, I, I'm okay," I managed to stutter but she knew I was fighting cumming.

Continuing to fuss in fitting the dress l on me was of little help for me. She had zipped up the back, once I'd stepped inside, and I relished the tight feeling about my mid-section and the rubbing against my nylon sheathed legs.

Helping me step up on the tailor's platform, she set about pinning the hem of the formal. Little was said and she had me turn this way or that as her critical eye made sure the hem would look fine.

It got really tough when she wanted me to turn just so and reached just under the dress and put her hands on my legs to position me just as she wanted.

"That's not going to push you over the edge will it, if I touch your legs like that?"

"N,n,n, no, I'll be all right," was all I could stammer, but my cockette was standing out straight inside my panties and made the front of the dress poke out, too.

Kathleen then began moving me about more and more, each time reaching farther up under the skirt until her fondling of my legs was at the top of the reinforcement bands. I was shaking like a leaf and finally muttered, "I think we need to pause or I'll be having a problem."

Kathleen smiled up at me and knew I didn't say the word 'stop' but wanted a pause. It was just what she wanted to hear.

"Well, I think we've got it done, dear," she told me. "Step down and let's get this off you and then I'll try it on."

She unzipped the back and helped me step out of the tight straight skirted dress. My raging hard cock was bouncing inside my panties and there was no way to hide it.

"I think you are enjoying helping me on this," she said, looking down at my stiffy inside my panties.

"I'm sorry," I muttered looking down at the floor and blushing even a brighter red than before.

"No apology necessary, Darling," she replied. "I think we are both enjoying this. Your kneecaps were bouncing up and down inside your nylons and it told me this is a lot of stimulation for you. It must be hard on you, my darling."

Laying the dress across the bed, nearby, she helped me out of the half-slip and left me standing there surprised as she took off her own dress.

The next thing I knew, she was before me wearing a white satin six suspender garter belt holding up her dark taupe nylon stockings, and a pair of water sheer white nylon brief style panties. Her shaved mound was clearly in view as were her bare breasts.

Acting as if she didn't notice my stare at her pussy through her ultra-transparent panties, she stated, "I can tell if the bra cups will work right with the dress if I had a bra on when I try it out. That's why I decided you wouldn't mind me being braless."

With trembling hands I helped her into the half slip and then the dress and zipped up the back for her.

It fit her like a glove and the hemline came to just above her knees and hung in a perfectly parallel line to the floor.

"Excellent!" she exclaimed as she studied the results in the mirror panels. "You have been such a big help and I so appreciate it."

With that she had me unzip the dress for her so she could hang it up ready for sewing along the hem. As she did so, I turned and began gathering up my jeans and shirt, etc.

Coming over to me, she softly said, "Thank you so much," and shocked me with a kiss - a long lingering kiss. "May I call you 'Erica' like Alice does when you're wearing your pretty things?"


"S-sure," I managed to say.

"Good, Erica, but I need to properly thank you for being such a good sport and so much help. You've earned a reward."

With that she dropped to her knees in front of me and slipped my panties down to the tops of my nylons. Stroking me, and looking up at me, she uttered, "We need to get this thing soft so your pretty panties don't tent out in front anymore. It's not very lady-like," she laughed.

Kissing my cockette, she quickly engulfed it in her lips and slid it inside her mouth. She began sucking my cock and I realized Alice wasn't the only highly talented cocksucker in this house.

It seemed like moments and I was holding on as I came with an explosion and Kathleen swallowed it all.

"Thank you, Darling," she whispered in my ear before kissing me deeply and letting me taste the residue of my cum in her mouth. "Actually, we both needed for me to suck you off. I've wanted to do that for you for the longest time.

"We've still some time," she told me, "As Alice said she wouldn't be back before 4 o'clock. Would you enjoy a cup of tea with me?"

Nodding my agreement, she opened her closet and handed me a sheer pink nylon babydoll nightie. Donning a sheer white one, herself, she led me through the house dressed as we were to the kitchen.

As the tea brewed we made small talk and she told me all about the exploits that Alice and I had enjoyed. It was unsettling to find she knew all about my going down on her daughter behind the barn and wearing her panties that night.

Gathering up the empty tea cups, after we'd finished our tea and little chat, Kathleen stood next to my chair and leaned over facing me. Kissing me again, she pulled down the top of her nightie and held one of her breasts up to me, muttering, "Kiss it, Darling, kiss it."

That was all it took and I was suckling first one breast and then the other and fondling both as she stroked me through my panties.

Finally breaking away, she held out her hand and led me back through the house.

In the bedroom she slipped her nightgown the rest of the way off and let it fall in a silken puddle at her feet. Then she did the same with mine.

Walking to the bed, she pulled her panties down as she kicked off her high heels and then pulled mine down and took off the high heels she'd put on me.

Pulling me to her, she kissed me deeply as she pushed her bare breasts against me. As my hands came up to feel them she pushed her tongue in my ear and licked it murmuring, "Fuck me, Honey, fuck me."

She pulled us back onto the bed and spread her legs as she reached down and guided my hard cock into her already wet pussy.

I was surprised that it slipped in easier than with Alice, and I'm sure Kathleen noticed. Nonetheless, she wrapped her legs around me and I was thrilled to note the silken sensations of her stockings and that was increased when they brushed against the pair I had on.

I pushed fully into her and then we were fucking like mad. "Cum in me, Honey," she whispered, "I've already cum once and am about to do it again. I can't get pregnant, so fill me, Darling."

Crying out, she came hard as I loved the sensations of fucking this beautiful brunette with the big blue eyes. I kept at it until her orgasm subsided and she kissed me deeply.

"You haven't cum yet, have you, Darling," she whispered in my ear. "I'm glad I was able to suck you off earlier so you'd last longer now."

With that she somehow managed to roll us over without my coming out of her pussy and then she began riding up and down on my cock as she kissed me and kept her beautiful breasts rubbing against my chest.

It only took a few more moments and I began to shudder, which caused Kathleen to urge me on and have a good cum.

We both soared into climaxes and then finally settled down. We lay there for several minutes and I began to feel my cum trickling out and running down onto me.

Kathleen eased herself up and moved farther up over me. Lowering her bald pussy to my mouth she told me, "Show me what a marvelous cream pie cleaner you are, Darling."

Somehow I managed to try to please her, but in the process found myself liking it and enjoying what I knew was the taste of both of us. I kept at it until there was no more cum left and she had another climax.

Sliding off me, she kissed my sloppy wet face and cuddled with me on her bed.

"I'm glad you aren't wearing make-up right now, Erica, as it would be a mess. You are a very good cunt licker and I hope you'll do it for me again."

I smiled and kissed her when she pulled me close and murmured "yes, I will."

"Good," she replied, "I may ask you to do this every once in awhile. Alice expected me to want you for repeats as she knew the plan."

With that we took a shower together and I was treated to my first time doing so and learning how to properly, and lovingly, wash a woman.

Watching me dress, Kathleen told me it was wonderful having me there acting as a maid for her with the gown. "We're a bit late in opening our cottage at the lake," she said, "Would you like to come out Memorial weekend and help us with some of the items we need to do? It would be just you, Alice, and me as the two younger girls are off with their grandparents for their annual start of summer trip."

"Gosh, I'd love that, but I don't know if I can. I'll have to ask," was my reply.

"Have your mom call me," she advised me, "I think she'll let you go once she knows I'll be there to chaperone," with that she was laughing.

I was slipping on the garter belt and putting on my nylons as Kathleen observed me. "Good girlish habits, " she intoned as she continued to watch me dress.

Stockings on and gartered tautly, she grinned as my panties were pulled up in place and my cockette reacted to the sensations.

"We'll expect you to dress only as a girl all weekend. No male clothes for you once we're there. We'll leave Friday afternoon and not come back until Monday. You will be our 'maid' for the weekend and we'll treat you like the girl you'd love to be."

I still didn't have my jeans back on, yet, and Kathleen giggled as she saw my 7 inch 'cockette' fully hard again and pushing out the front of my panties.

"My, oh my, you rejuvenate quickly! That's a good sign!"

Little did I know just what all Kathleen and Alice had in mind for me the upcoming weekend. My horizons were about to be expanded beyond what I'd imagined as it would include my having sex with a guy.

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AnonymousAnonymousabout 1 year ago

I live how I can relate to Erica as I always wanted to wear such things as a lad and your story creates a vivid picture of this fantasy and the experience of sharing with an older woman in similar feminine things is so erotic to me.

sweeterika2sweeterika2almost 2 years ago

hi darling love reading your stories Kissses, Erika

Synthia44Synthia44almost 2 years ago

Damn, you are a great story writer. This is the second of your stories that I have read and it too is a great write. I'm envious of Erica. You must be hard all the time when writing these stories. I know I am. Fantastic story with a great ending. Looking forward to reading your other stories.

AnonymousAnonymousabout 2 years ago

Absolutely love this story. I wish my highschool girlfriend was as open to my wanting to wear lingerie. And a mom who supports and encourages would be icing on the cake.

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