Shopping with Lynn Pt. 02

I was back at work a few weeks after Lynn's birthday when my cellphone dinged at my desk, signaling a text. I didn't recognize the number, but it was the Charlotte area code, so I opened it up:

Hi Jim, this is Jennifer from Nordstrom's. Lysa gave me your cell. Hope Lynn enjoyed her birthday present! Hey, my BF and I would like to invite Lynn and u over for a play date? I'm sure they'll hit it off... LMK-- Jennifer

Well, this was a certainly new development! I honestly had no idea how Lynn would respond to the news, and if she'd be interested in another couple. It was a huge step for her to just meet me, so I really didn't know about this. I texted her:

Ur not going to believe this, but your new pers shopper Jennifer just asked us over for a "playdate"! Whatcha' think? XXXX, J

I could not imagine what was going to go through her mind when she read that, and not getting a quick response I went back to work on what I had been working on. I got her reply about an hour later:

Oh Jim, what should we do? I'm so new to this, yet I don't want to mess it up either. If you'd like to, though... and Jennifer was cute. I say Yes to the Dress! XXX, Lynn

So, there it was. Just the thought of the two gurls going at it was a vision enough to entice me, and Lynn did have a point about Jennifer. It's not often a sixty-something man gets invited to play with a twenty or thirty-something woman and her gurl-friend. It'd be three clits and one cock...

Jennifer, I checked with Lynn and she'd love to, as would I. Just text me the particulars and we'll be there. Jim

We made plans to meet up at their apartment on her day off from Nordstrom's the following week. My job did not require my sitting at my desk all day, and Lynn was between jobs, so it was going to work out perfectly. I told her that Lynn would be dressing up, and that her gurl friend should too. She agreed and said they were both looking forward to it.

The day could not come soon enough. Lynn and I agreed that she would bring her lady clothes over to my hotel room and change there, and then I'd drive us both over to Jennifer's apartment. I was still living in another town on the North Carolina coast and had to travel to Charlotte to see her. Lynn and I chatted almost every day until then, the excitement building between us. Typically, our chats had me taking her through to orgasm, but the last few days before today I held her off, making excuses. It was innocent enough and for a good reason I thought. And now, because of these chat sessions, I knew all her deepest fantasies, one or two of which were about to be realized tonight.

The knock on my hotel room door was Lynn. "Oh my god Jim, can you believe what we're doing?" she asked me as soon as I opened the door. "Hello you!" I responded the way I always did upon greeting her, but this time kissing her pretty lips, "I'll tell you what we're doing," I said after we broke the kiss, "we're about to have a great time! If Jason is as hot as Jennifer is, we'd be nuts to turn them down. But I tell you this Lynn, it is entirely because you're a gurl. It sure ain't MY good looks, babe. You're probably the only CD who Jennifer ever helped in the store. Now, go into the back and change into the beautiful woman you are."

She smiled at me, kissed me on my cheek, and took her gym bag with her into the bedroom. A few minutes later, I could hear the shower running. I hadn't seen her in a few weeks, so I really wanted to join her, but one thing would lead to another, and we'd both end up being spent before even leaving the hotel room.

If men thought their wives took a long time to get ready for going out on a date, it's nothing compared to a Cross Dresser. It might be the (relative) lack of experience, or maybe a keen desire to get everything just right, but it sure was taking her a while. Not that I was complaining, mind you.

But my god was it worth the wait. When the bedroom door opened, and she came out with a smile and a "Ta-Dah," I was flat-out unprepared for what I saw. Lynn was fully made up (thank you Madeliene at the Bobbi Brown counter) and wearing a strapless blue cocktail dress. She must also have been wearing either her corset or the bustier that we had bought, because the dress fit her closely and well. I was not at all sure how she was holding up a strapless dress, but I wasn't about to ask.

"Lynn, Oh my god. You are so pretty, and that dress- it's perfect!" I told her truthfully.

"Sorry I took so long," she started to say. "Stop," I cut her off mid-sentence, "The view I have right now makes up for it all, and a woman never apologizes for taking her time getting ready. I am such a lucky guy, you know," as I leaned in to kiss her. And as I did, I detected just a hint of perfume. "What is the scent are you wearing?" I asked her.

"Oh, just a couple layers of Jo Malone," she replied, "do you like it?" To which I just touched my nose to her neck, inhaled it in and smiled back at her. She knew I did.

"These two young'uns we're about to see have no idea on what's coming, do they girl?" That little remark got the nicest smile I think I've ever seen. "Let's get over there" I said, placing her wrap around her shoulder, donning my sport coat, carrying her bag and grabbing our two masks that we'd need to walk the hallway of the hotel to the car.

I think the COVID mask gave her just a little bit more confidence to dress in public, something she never did before our little shopping trip. We passed a couple in the hallway of the hotel, and they smiled at her, the man clearly looking at her desiringly, and I could tell he had no idea. When we got to the elevator, I leaned in and whispered to her "I think you added a fan to your fan club back there, you know," to which she immediately blushed a scarlet red.

We rode the elevator down to the lobby of the hotel and I led her out to the parking garage to my car. I opened the passenger door to let her in, and she of course looked at me while she was getting in and said, "No peeking, you little perv!"

That's the problem with cross dressers... being born men, they know all the guy secrets. On the other hand, she had caught me before doing the same thing.

I got into the driver's seat of the Lexus and looked at her. She had taken her mask off and was just radiant with the excitement of the evening to come. "Are you in chastity?" I asked her, knowing the answer as I held out my hand for the key. Her radiance was heightened by the blush in her face as she handed me the key. "Thank you," as I kissed her. The ease of her blushing was one of the things that endeared her to me.

We chatted as I drove us to Jennifer and Jason's apartment, Wayz guiding me through Charlotte to a very trendy area that tends to draw professional couples. I had thought our first "out-date" would occur at a gay bar, where cross-dressers are more accepted, but this double-date at their home was working out even better. Lynn's wife was away on a business trip, so we had the evening free without worry.

"Here we are now," I told her, as Wayz led the way. I pulled into one of the open spots of the apartment complex and parked the car.

"These are very nice" she said, and I agreed with her. "Together, they must have a nice income to be able afford one of these."

We donned our masks to walk through the lobby of the apartment complex, where we were greeted by a lobby attendant. "Roberts," I told her, "Heading up to apartment 1220, Jennifer and Jason..." "I have your name right here, Mr. Roberts," she said as she had my name, "Welcome, and the elevators are behind me to the right."

We walked around the lobby to the right and found them, Lynn very quiet and holding my hand. "I feel like I'm a Bond girl," she said to me quietly as the elevator doors came open. "Lynn, in that dress you look like a Bond girl," I assured her, "a Bond girl about to be the center of attention."

The elevator rose to the twelfth floor and opened; we saw a small sign directing us to 1211-1220 to the left. "Looks like 1220 is all the way at the end of the hallway" I told her. We walked down the hallway hand in hand. Once again, as on our first date, I could hear the lock of the chastity device lightly clinking against the hard plastic shell. She looked at me, reddened (of course) and smiled through her mask. I stopped her just short of the apartment, and we removed the masks. "Let me look at you," I asked her. I took the wrap from her shoulders and adjusted the pearls around her neck. "Bond girl," I told her as we approached the door, and I rang the bell.

Jennifer answered the door. "Good evening you two," she said, "Come on in, please!" she said as she stepped aside to let us in. She shut the door behind her.

"Lynn, you are beautiful, and I love that dress!" she said, and looking at me "My Jacey will be out in a minute. She had a long day at work and needs just a little bit more time." She showed us around the apartment, and the view they had of the city. They had a gas fireplace which was lighted, and two sofas in front of it, opposite each other with a coffee table in between.

"Jim, would you mind pouring the drinks?" she asked me, "I think three Cosmo's for us girls, and make whatever you'd like for yourself." She led Lynn over to one of the couches and sat down.

I found all the ingredients for the Cosmopolitans there on the bar, along with gin and Noilly Prat vermouth for mine, even some bitters, bless her. Jennifer was clearly punching above her weight. I made the girls' drinks up, in martini glasses, and my own on the rocks with a twist. I put them on the tray she had set there with some delicate-looking cheese straws, and brought them over to the sitting area where they were.

"Did I have everything you needed Jim?" she asked.

"Perfect." I replied as I handed the two their drinks and sat down with my own.

"Lynn was just telling me this is actually your first double date?"

"It is and thank you so much for the invitation." I told her in all sincerity. "We really haven't been out as a couple at all, it's just too hard," I said as I looked at Lynn, reassuring her.

"Believe me, I totally get it," she said, "that's why I had to take the opportunity to get us together after the other week."

"You mean you don't normally take your personal shopper clients out?" I joked with her.

"Hardly. They're mostly older professional ladies with little time. I was glad to help Lynn here!"

The door to the bedroom opened, and out came Jacey. I stood immediately upon seeing her, a young lady entering the room. She was blond, long hair, very thin, and wearing a cocktail dress also, but as Lynn's was strapless, hers was demure and befitting her younger age. "How do you do, Jacey" I said as I approached her, offering her my hand, and leading her over to the sofa opposite to where Jennifer was and next to where Lynn was sitting. "I'm Jim, and this is Lynn." "Lynn, may I present Jacey....er" I stumbled, not knowing her last name. "Regent, Jacey Regent" she said as she offered Lynn her hand.

I looked over at Jennifer who was positively glowing and handed Jacey her drink. "Thank you, sir," she said as she took it. It was clear that Jacey was just as nervous as Lynn and would need me to lead. "Lead" a friend once told me, "Don't lead on."

"May I propose a toast?" I raised my martini, "To new friendships." That seemed to be the right words as the girls all agreed and took sips of their drinks as well.

We settled into a nice conversation about how each of us had met. Jennifer and Jacey had been together for just over a year, with Jacey coming out to Jennifer about six months ago.

"Jacey started hormone replacement therapy about four months ago," Jennifer told us, "And is now developing breast buds, aren't you?" to which Jacey blushed and said "Yes, and I've noticed less hair on my face. But I am breaking out again." She pouted. "Just like a teenager, but this time a teenage girl."

"But your endocrinologist said that was normal and to be expected, didn't she?" Jennifer reassured her. "And Jason also made a sperm deposit before we started all this, in case we ever wanted to have children, isn't that right Jacey?" Jacey blushed as she nodded.

It was obvious that Jennifer was leading this conversation as the alpha female of their relationship. She was in a room with three cocks, at least one of which was caged and in panties and the other free but already stirring uncomfortably in my pants. She turned to me "We do love each other, but sometimes I have needs that can only be met by, well, by a real man. But my Jacey understands that don't you?" Clearly, I saw why I had been invited to an otherwise all-girl cocktail party. I finished my drink and stood up to make another round. "Ladies?"

I was making the second round of cocktails when I looked over at the two on the couch. They had moved closer together and were touching hands. Jennifer came over to me with the tray of cheese straws to refill, and whispered "I told them to get better acquainted, is that all right? Of course, that leaves us together, doesn't it?" She smiled at me and kissed me on the cheek. "Jacey can't get very far past third base, though, as I have her all locked up," she said as she pulled a key out from under her blouse similar to the key I had in my pocket. "You are so bad, Jennifer," I smiled as I showed her Lynn's key. Make that two cocks in cages.

When the second round of drinks were made, we turned to go back to the gurls, who had begun to kiss lightly. I knew Lynn was enjoying this as much as I was enjoying watching her, lightly kissing the younger one tenderly on the lips. I had told her previously that I didn't want to share her with anyone but decided that this was worth retracting that statement.

"Here you go, in case either one of you gets thirsty or needs to come up for air" I said to them, which got them giggling. It was the right thing to say. In the meantime, Jennifer had gone past me and closed the blinds a bit to the patio they had. The sun was going down, and I could see the lights of Charlotte starting to come on. She came back and sat back down on the other sofa in the room, opposite Lynn and Jacey, and motioned me to sit down next to her. The two gurls drank a bit more of their drinks and started to kiss again.

Jennifer and I snuggled closer together to watch the two gurls begin to make love. Jennifer leaned into me and whispered "Jacey has been wanting to make it with another gurl for a long time. Her hormones have been raging," and then kissed me on the ear as we watched.

Lynn was taking the lead it seemed, being older and not under the influence of the male-to-female hormone treatments the younger was receiving. She was feeling Jacey's young breast buds through the young woman's dress, and began to unzip it, all the while kissing her with a passion formerly reserved for lovers. As the dress came loose, Jacey leaned forward and allowed Lynn to pull it off her shoulders and down, exposing her black lace bralette, her nipples clearly erect and pushing against the lace. Lynn reached under the bralette and began to softly tweak and rub the newly puffey nipples, tender from their rapid growth these last few months.

Jacey arched her back, allowing Lynn to totally remove her dress, revealing matching black lace panties with a significant bulge inside. Her stockings were held up with garters and she had previously removed her shoes. Jacey was now naked before us, except for those bits of lace covering her caged clit and young breasts.

"Lynn, come here to me," I directed, as she left poor Jacey for just a moment. I stood up, kissed her deeply, her face already wet with the lovemaking that had already started. I found the zipper that was holding her own strapless dress tight around her body and unzipped it, allowing her to step out of it, exposing her undergarments. Lynn had worn a black lace bra, but unlike the younger woman there on the couch, she also had on the pretty black bustier we had bought from Jennifer at the store. She also was wearing the crotchless version of the lace panties, which allowed her chastity device to protrude freely, her clit clearly swollen within the cruel plastic tube. "That's better, girl" I told her, and gave her a gentle nudge back to her charge.

The two gurls now let their passion go, hands on breasts, lips on lips, grinding the two encaged clits against each other. Lynn removed Jacey's bralette and sucked on the breast buds. Jennifer whispered again into my ear "They have been very sensitive this week, they must be hurting!"

If they were aching, Jacey was not showing it as Lynn had each one in her mouth, alternating licking while tweaking the other, then switching nipples. Lynn, nor I for that matter, had ever seen such young breasts and breast buds, albethey on a twenty or thirty-something year old male. Jacey, for her part, clearly wanting to suck on Lynn's breasts as well, reached behind Lynn, undid her bra clasps and pulled the bra off of her fellow cross-dresser. Lynn's nipples were already hard, and I knew they were sensitive. Jacey leaned into them and suckled.

"It appears your Lynn is quite a leaker, isn't she?" Jennifer asked me, noticing the strands of precum oozing out from the slit of the chastity device. "Yes, she is" I told her, "Is Jacey?" I asked. "No, and not at all since beginning the hormone treatments." We were kissing more and more often as the lovemaking we were witnessing between the two gurls was stirring us. She reached down to my crotch and grabbed my manhood through my trousers. "My god this is going to fill me up so nice" she said, squeezing it. "How does Lynn take it?" she asked. "Slowly, and with lots of lube" I responded. I was no great size king at six inches, but fairly girthy. I let her continue her fondling.

I unbuttoned her blouse, revealing bare small breasts with hard dark pink nipples. "You like?" she purred. Not even answering, I took each into my mouth and began to lick them. The room was quiet, save for the occasional moaning and the near-constant licking and slurping noises coming from each couple. "Jim," Lynn called out my name, "My key, may I have the key?" I took my mouth away from the nipple I was suckling and saw Jacey's key around Jennifer's neck. "May I have the honor?" I asked her. Jennifer gave me Jacey's key and I took Lynn's from my pants pocket and went over to them. "OK, girls, who is first?" I asked teasingly, kneeling in front of them. I took the key to Lynn's and undid the lock, pulled the tube off her clit which now free of its bondage, began to immediately swell. I then pulled the other half off from around her nut sack and she was free, if a little sore.

"And now yours, young lady" I said to Jacey. I pulled her panties off, leaving her garter and hose intact, leaving them to Lynn if she saw fit to remove them, but which I doubted. There was her clit, equally straining against the inner walls of her device. Not being able to help myself, I leaned down and licked her hairless balls, still taut and held in place, thrust forward from her pelvis. Not wanting to deprive Lynn any longer than necessary, I undid Jacey's lock and similarly removed her cage. "Well, Lynn, looks like someone is going to have her first uncut clittie cock tonight" as I saw the uncircumcised cock begin to harden. I backed out of the way and let Lynn kneel where I had been, between Jacey's legs and as she watched it grow, the foreskin retracted on its own behind the head.

Lynn was rapidly becoming an accomplished cocksucker and took the growing gurl clittie cock into her mouth. Jacey was on the smallish size, so Lynn was able to take it to the root. She knew what I liked from when she sucked mine and did the same thing on Jacey. Lucky gurl!

Jennifer and I admired the view of the lovemaking in front of us, Lynn bobbing up and down on Jacey, Lynn still wearing the bustier, garter and hose. Her own clittie cock and sac swaying between her legs as she sucked Jacey. Her butt cheeks were spread slightly, letting us occasionally see her sweet rosebud between them and above the sac.