A Trainer for Lynn Ch. 01

I was to pick Lynn up that morning. Her wife Teri was out of town on a business trip and was okay with me coming over. I doubt she would be pleased with where I'd be taking her husband today, though. I told Lynn to dress comfortably as we'd be going out, and I left it up to her to interpret what "dressing comfortably" meant, from full en femme to just her pretty underthings.

I pulled into her driveway just before ten and went up to the door. After a quick wait, she answered the doorbell. "Hey you!" I greeted her as I always did, in our own little private way. She smiled back beaming and let me in. As the door closed behind us, I reached up and took her face into my hands and kissed her softly on the lips, as the lover I was. "Mmmmm" she replied.

She was dressed beautifully, in an elegant low cut pink V-neck blouse and white capris, with flat sandals. Her nipples were clearly visible through the fabric of the blouse, erect and darkened. "You're beautiful, you know that?" I said as she blushed in response, "Where are you taking us today?"

"Literally, to a friend's house," I replied, "figuratively, to a place you've never been before."

I could see her perplexity on her face, as she had no idea where we were going. We went out to the car, and I held the door for her as she got into the passenger's seat. She looked straight into my eyes as she bent over sitting down, her blouse opening and revealing her bare breasts supported only underneath by a demi-cup bra. She knew I liked what I was seeing.

Our friend's house was about an hour from hers to the west of Charlotte, so we filled the time with conversation interspersed with coy sexual banter, as new lovers will do. During this talk, she would reach over and touch my thigh, running a finger from my knee up the leg.

We were in rural country, in the farm hills of North Carolina with houses far apart and among corn fields interspersed with forest. Before too long, I turned up the drive to our destination and drove another quarter mile or so to a nice colonial house surrounded by woods. "Well, here we are," I said to her as I got out and opened the door for her. "You're still not going to tell me, are you?" she asked.

"Sweetheart, you are so close to the surprise, why spoil it now?" I replied as we walked up the path to the door. "Nervous?" I asked her. "A little, yes" she said, holding my arm in hers.

I rang the doorbell and the door opened only a bit later.

"Hello, Jim" the owner of the house greeted us, "and you must be Lynn," she held out her hand to her, welcoming her in.

"Hannah Kay, may I present Lynnette G.?" I said to Hannah and, "Lynn, meet your friend Hannah."

"Oh my god" Lynn gasped. The look on Lynn's face was priceless. They had chatted for months on the same site where Lynn and I had met and I'm sure Lynn had never imagined meeting. Hannah and I concocted this plan also in the same chatroom. Hannah is also a cross-dresser, but much more experienced than Lynn. She suggested we meet after I just casually and even jokingly mentioned that she would have a lot to teach Lynn. She was not a dom by any stretch, in fact she's not even a top, which I would have to keep in mind, but she was willing to play into my little scheme, especially if Lynn would share me for the day.

"Come in, you two" Hannah beckoned. "Jim, please have a seat here in the living room. Lynn, let me show you around. I'm sure you'll want to freshen up?" The two ladies went off holding hands laughing and chatting, while I helped myself to some coffee that she had thoughtfully set out before we had arrived. The house was well-appointed and very tastefully decorated. Hannah I knew lived with another dresser, although her roommate was not there today.

"I hope you don't mind I helped myself to coffee?" I asked Hannah when she returned.

"Pshaw," Hannah shrugged it off, "that's why it's there. It's all about pleasing my guests, isn't it?"

She continued, "She really had no idea, did she?"

"No, not at all," I replied, "and certainly none of what's to come."

"Well, I think she has an idea." Hannah said, "We passed through my bedroom and I'm sure she saw all my toys laid out."

"The training bench?"

"There too, not to worry. Did you have problems finding the place?"

"No, not at all. Wayz did all the work" I admitted to her honestly, "Ah, there she is!" I exclaimed and stood as Lynn walked back into the living room.

"Please sit, Lynn," Hannah said as she motioned to the ottoman near me, "here is some water if you're thirsty, dear."

"Thank you, Hannah," Lynn said as she took her place on the ottoman, "I am a bit overwhelmed with all of this. And all those toys?"

"Well, we may not get to ALL of them today dear, I must admit" Hannah said reassuringly.

"So, would you like to know why you're here?" Hannah asked. Lynn nodded yes.

"Jim thought it might be nice to get together and play, and that I impart some of the things, or rather, techniques I've learned in my life as a 'woman'," Hannah began, "Would that be okay? It'll all be fun!" And then she added, "Of course, you'll be the... how shall I say... the focus of our attention?"

Lynn took a sip of her water. This was all new to her, but certainly she was interested. "Yes, I'd like that. I'd like that very much. We, Jim and I, have played with another couple before and we really liked it."

"Wonderful, then. Let's start with you standing up and removing those pretty capri pants, shall we?"

Lynn did as she was told, stood up and took off her flats and her capris, leaving her in her blouse and panties.

"Very pretty panties, dear," Hannah told her, "Now come over here next to me and let me see your pretty bottom."

Lynn walked over to Hannah and turned around and faced me.

"Let's remove these panties, shall we?" Hannah told her, which Lynn did, exposing her backside to Hannah and her caged clit to me.

"Now Jim, has she ever been sized?" she asked of me.

"No, do you think we should do that now?" I replied.

"Oh definitely." Hannah stated matter-of-factly as she reached to the side table and opened a mahogany box. Lynn looked over her shoulder and saw the box contained a set of ebony butt plugs, ranging in size from very small and thin to the largest, one with quite a girth.

"I've found that for gurls like us, it helps having the correct size plug, so that it makes it easier for us to receive our men." Hannah pried apart Lynn's cheeks and probed her bum hole with a finger. "There there now Lynn, it's just us girls, isn't it?" she reassured her, "I think a number two would be a good start. Jim, do you find her a bit tight?" she asked me, ignoring Lynn.

"Yes, but enjoyably so" I replied.

"As I thought," she said to me, and to Lynn, "Did you douche as I instructed you?"

"Yes, ma'am" Lynn replied and blushed as she looked at me.

"Good, then we'll have no problem slipping this in, will we?" Hannah said as she handed a tube of KY to her. "Lubricate it well, dear. You know where it's going." And to me, she said "Lynn told me she always douches before meeting you, because of how you enjoy her, and that she did this morning. But after an hours' drive, I thought she might want to do so again."

Lynn slathered the warming jelly onto the butt plug and set the tube down on the ottoman. She bent over slightly to receive the smooth wooden implement. Hannah stood up and held Lynn by the shoulder as she pressed the glistening object into her rosebud. "Now spread those cheeks just a bit to help me. Ahhh, there you go. Push against it, you know you want it."

"There you go, it's in." Hannah said as it slipped silently into Lynn's rectum. "Jim, come here, I want to show you something."

I went over to Lynn's other side.

"Here, take hold of it," she instructed me, "Wiggle it from side to side. You see how there isn't much give? That's what we're looking for in a good fit. Not too big, of course, as you still want her tight, but just enough to make it easier for you to enter at will." She all but ignored the recipient of the plug in talking to me. "Keep bending over, dear," and to me "I think you'll find it easier to enter her after this has been in for a bit., and she won't have to strain as much to take you."

"Well, now that that's done, let's sit back down. Lynn, it's a leather ottoman, so don't worry about leakage onto it," Hannah said as we sat, Lynn somewhat gingerly, "That's all right dear, it won't slip out."

Hannah had asked Lynn to refill our coffees, and we chatted some more, completely ignoring that Lynn was naked from the waist down, plugged, and caged. It was an effect I could tell was affecting her profoundly. As she bent over to pour the coffee, her breasts were plainly visible down her blouse, as was the plug from behind.

"I must tell you, Jim, I am envious of the relationship you two seem to have developed," Hannah said, ending the chit-chat. "But what sign is there of her commitment to you? A tattoo? A piercing? Or heaven forbid a branding?"

"No, nothing like that" I told her.

"Would she wear your collar do you think?" Hannah asked, "At least while you were together?"

"Yes, I believe she would," I said reaching into the pocket of my sport coat. We had talked about this before, Hannah and I. Hannah was deliberately referring to Lynn in the third person, I could tell, to heighten her sense of subjugation.

"Lynn, go kneel before him." Hannah directed, and Lynn did so. "Jim, you need to ask her, that is something I cannot do."

"Lynnette, do you accept my collar as a sign of my leadership and my desire for you? I promise never to abuse you, nor will I abuse the power the collar will have over you." I spoke to her from the heart, looking her in the eyes.

"Yes, sir, willingly and without question," she replied. After she kissed the collar, I strapped it around her neck and fastened it. She touched it lightly and smiled. Smiled as I kissed her.

"Well promised, both of you!" Hannah applauded. "Now, let's get down to business, shall we?"

"Lynn, let's lose that blouse, shall we?" Hannah again took charge, even as Lynn and I were continuing to delicately kiss. "Help me with it, Jim"

We each took a side of the blouse and lifted it over her head and off, exposing her breasts and nipples, proud and erect, her breasts laying in their demi-cups

"How about we put this new collar to work?" Hannah suggested, reaching into her purse and pulling out two nipple-clamps with small chains attached to each. "Jim, I'll do one, and you can do the other," she said as she handed me one of the clamp and chains. We attached one end of each to the collar's D-ring, and the other to each of Lynn's nipples. "How wonderful it is that she wore a demi-cup bra today, isn't it?" Hannah asked her, "These clamps aren't too strong, are they? You'll be able to tolerate them, I should think."

Lynn nodded her head and closed her eyes, focusing on the clamps, her nipples, and the chains connecting them to her new collar. She looked at me with eyes moistening, "I'm just so happy right now!" she whispered to me, "I do so want to please you."

"Well then, let's go for a walk shall we?" Hannah suggested as she produced a leash.

"Oh, my!" Lynn gasped.

"There there, now dear, I can assure you that I've had men lead me around my own back yard. It's perfectly secluded and fenced off, my nearest neighbor is a mile away, and they works all day anyways. Although for me it was punishment, for you it's a learning experience, isn't it?" she assured the younger woman as she clasped the leash to the D-ring. She handed me the leash and told Lynn to slip her shoes back on. "Of course, there's no telling when a curious teen-age boy may be wandering the woods." I'm sure she added this to heighten Lynn's anxiety.

I led her out the back door, Lynn clad only in her demi-cup bra, nipple chains and clit cage (plugged still, of course.) I asked Hannah "She seems a bit red in the face and upper chest above her breasts. Do you have hat or something to keep the sun off her face?" I knew it was all for show because Lynn was so quick to blush, and of course this talk only added to the redness. I admit I was getting into this, albeit at my poor Lynn's expense. Was I already breaking my vow not to abuse the power of the collar?

"Sure, be right back!" Hannah said as she went back into the house.

"You okay Lynn?" I asked.

"I'm so happy, Jim, I've always wanted this. Lead me on. Take me where you want us to go," she told me.

Hannah came back with a pretty yellow flowery sun hat for Lynn, which she placed on her head.

"Goodness me, look how sunny it is!" Hannah declared, "Fortunately, I brought along some sunscreen!" She handed me a bottle of coconut-scented suntan oil, the kind with only minimal sun protection but smelled so nice. I promptly squirted oil on both my hands, both of Hannah's, and all over Lynn. We rubbed it all over her body, paying particular attention, of course, to areas of a woman's body that normally don't see sunshine. I knelt before her, squirted the oil even into her chastity device, rubbing it all over her ball sac and the inside of her thighs as Hannah concentrated on her back and buttocks. Hannah undid the clasps of Lynn's bra, exposing the bottom half of her breasts, which I slathered with oil. We maybe might have gone a little overboard, as oil was soon dripping from her still-clamped nipples. She was covered forehead to toe in coconut oil as I took the leash back into my hand and led her on our walk around Hannah's yard.

"I think this is actually my favorite part of the house, even though it's the garden. Does that make sense?" Hannah asked me, "I can spend hours out here during growing season, weeding and feeding, watering and transplanting."

It really was a pretty garden. We led Lynn around the pea-gravel path, the small stones crunching under our feet, her oiled skin glistening in the sun. The poor girl was plugged, caged, and clamped but to me she was radiant, although that might have been the sun reflecting off the oil.

"Lynn, are you enjoying our walk?" Hannah asked her.

"Yes, ma'am I am," Lynn replied.

"Well, I know Jim is. He keeps having to adjust his cock. Growing is it?" Hannah playfully asked me, to which I smiled back.

We completed our walk back at her back porch and toweled Lynn off a bit to prevent any of the oil from getting onto the carpeting. She yelped a bit as I removed the clamps from each nipple to dry them. I tried to soothe them as best I could with my tongue, knowing how sensitive nipples are immediately after being unclamped. Painful, actually. Still, she wasn't complaining.

I removed the leash and the nipple chains from the collar and walked both women inside. "Where to now Hannah?" I asked.

"Let's make our way into the bedroom. Here, let me lead the way. You take her collar though." Hannah led us through the living room into the bedroom area where she and Lynn had been earlier.

"Lynn, why don't you sit on my little training bench here while Jim and I undress."

We left Lynn sitting on the bench while Hannah led me to change out of our clothes. Visible to Lynn were all Hannah's toys, dildoes of various sizes and shapes, clamps, crops, specula. To say that Hannah was experienced is an understatement. We weren't going to use but one or two on her, but it would heighten her sense of anticipation.

"How do you think it's going?" Hannah asked me after we closed the door to the bathroom.

"She is in heaven," I replied, "From the beginning, she has always called me Sir and has always enjoyed my instructions. I know she is getting into it. Thank you for this, Hannah."

Hannah removed her dress revealing a red lace bra, a waist trainer and matching red lace panties. Her fishnet hose were supported by a garter, the straps of which ran under the panties, of course. "That walkabout in the yard I told you about in the garden? That was punishment for my having worn the garter straps outside the panty," Hannah said, "I didn't make that mistake ever again."

"I don't think I'll ever be that harsh on Lynn," I admitted.

"That harsh? Ha! Hardly. That man stripes me for the littlest things. Of course, I mostly deserve it." She leaned over to me and kissed me. "I can't bear to think about what he'll do when I tell him about this!"

"Oh my, I do indeed have reason to be jealous of Lynn. That is quite a tool you have there, mister" she said taking my cock into her hand, "Remember, I get a piece of it too today. And I love the brass cock ring. So prominent!"

We went back to the bedroom where Lynn was diligently sitting in anticipation.

"Well, then where were we?" Hannah asked, "Ah yes, let's see how good a cocksucker you are, Lynn. Jim, would you present it to her?"

I walked over to the bench where she was, my cock swaying back and forth as I went.

"Always kiss it first, dear. Remember how you love it, how it drives your passion." Hannah said this as she sat down on the training bench with Lynn. "Good girl, dear. Just go at it as you normally would."

"Jim, is she able to throat you without gagging?" Hannah asked me in a rather matter-of-fact manner, then to Lynn, "Keep eye contact with him as best you can, dear."

"Not really, Hannah," I said to her, "I was kind of hoping you had a strategy for that. I know she wants to be the best cocksucker she can be." I was glad I wore the cock ring, as I could take my mind off of the blowjob I was receiving and not worry about getting at all soft.

"Not to worry," then to Lynn she said, "Let me see how far you can take him into your mouth."

Lynn tried, she really was trying, and to her credit could get about four inches of it in before gagging.

"No. Here dear, let me show you. Swallow as you take it in." Hannah demonstrated what she was talking about as she took it all the way down to the root, cold. She did it a few times to make her point. And maybe to show off a bit. "And eventually, I'd like you to be able to do this." She took me to the root, then stuck her tongue out and licked the front and bottom of my balls. The woman must have had zero gag reflex!

"Okay, now you try. Remember to swallow it, not resist it"

Lynn tried a few more times getting a little better, but still gagging.

"That's okay dear. We all start somewhere. Let's use this bench," she said as stood up. She motioned Lynn on her back and leaned her neck back and over the front of it, which had a leather padded curved end. "This is a training bench, although we could have used the side of the bed. You see, I can adjust the height of where your gullet is in relation to the cock. Jim is tall, so let's raise you up a bit." She stepped on a pedal which triggered motors that indeed raised the bench, and my prone lover, up to where my cock would easily slide into her mouth without me having to bend my knees. "How's that, Jim?" she asked. I gave her the OK sign.

"Now Lynn, I don't have to strap you down, do I?" she asked, "Although you may enjoy the feeling of extra submission that being strapped down can offer you."

"Hannah, is her collar loose enough?" I asked her.

"Good point. Let's loosen it a couple of notches. She just received it, so I doubt she wants to remove it so soon, now do you Lynn?" Lynn could only shake her head as she was already mouthing my penis, "We'll actually be able to see her throat enlarge as the cock enters it. And being horizontal with no bend in her neck makes it very easy for her to receive it without gagging too much. Go ahead and try."

I pushed into her mouth and as Hannah had predicted, we could see her throat bulge upwards in response to my cock. She did gag a bit, which was expected at this point, but she used her hands to push my thighs away. Which was unexpected, at least from Hannah's point of view.

"No, no Lynn, don't do that" she cautioned her, "Or I WILL strap your arms down. Jim won't choke you. It's obvious how much he cares for you. You need to show him the same amount of respect. He'll let you breathe, dear. Trust him."