14 years ago I posted a couple of stories from my first sexual experience, which…
Tricks
I stepped into our bedroom and saw my lovely wife Nancy sitting at her vanity applying a light blush. As usual, she was decked out in a fabulous array of lingerie. I was intrigued by her luscious curves adorned in delicious white nylon and lace. Nancy had recently began wearing garter belts on a regular basis and it drove me crazy. She had purchased five new ones in the last week alone. I would have loved to be wearing it myself.
“Hello Jack” she said to me.
“Hello dear” I replied. “Are we going out tonight?”
“Why yes we are.” She informed. “I have a dinner meeting at a client’s house tonight.”
“Oh really” I inquired.
“I want to try some of the new sales techniques I learned last weekend” Nancy said referring to our Florida trip.
“I’m sure you do.” I told her referring to her sex fest the prior weekend.
“You’re going to be there too,” she said clasping her pearls around her neck. “I know how much you enjoy watching all that cock in my pussy action.”
“I enjoyed watching it very much” I agreed.
“I’m so glad. But, we need to go by Lace Indulgence first” she informed.
“Are you going to get something else new for tonight?” I inquired of my sexy wife.
“Not really, we do need to get you some panties though” she said. “After all, I can’t let you keep wearing mine. I have to wear them to, sometimes anyway. And, I know you’ve been trying on some of my items before I get home in the evening.”
“What” I acted shocked. “I don’t want to wear panties.”
“Don’t be silly. Of course you do” Nancy said as she turned from her vanity, crossed her legs and slyly faced me. She had raised her eyebrow as if to confirm my lie. “Remember how much you enjoyed wearing my silky things in Florida? Remember how excited you got in them. Remember you wore them home on the plane. And like I said, I know you have been sneaking into mine almost everyday. I certainly don’t want you to stop now. You like wearing lingerie and I want you to keep wearing it. You’re such a little panty boy.”
Emphasizing little, she was right. I loved wearing her silky panties while she was getting fucked and just about any other time as well.
“I guess” I replied sheepishly. “But can’t you just buy me some and bring them back?”
“Absolutely not.” She affirmed. “I want you wearing a very pretty pair of panties tonight, at the party. Besides, if you’re going to start wearing them, you’ll need to try them on and get acquainted with the staff, so you can go back on your own. You can’t be a part-time wearer darling. From now on, you need to wear at least panties all the time. I really would like you to be wearing stockings as well. I know you honey and believe me, by the time you get in the store though, I think you’ll want to go back by yourself, often.”
“Surely they must be closed by now” I responded. I loved panties but I didn’t care for a client to see me in them and now was I going to wear them all the time.
“Oh no they’re going to stay open just for us” she said. “I explained our little circumstances and the owner was excited to meet you and really wants you to come in. My boss actually referred me to the shop for your needs.”
“You mean you told your boss about my fetish?” I asked.
“Well, when he was fucking me in our bed yesterday he wondered if you minded him having sex with me.” Nancy said. “I simply explained that you couldn’t possibly mind since you have such a small dick and enjoy wearing ladies’ lingerie. He suggested taking you Lace Indulgence. They cater to your needs.”
Embarrassed and getting very hot at the same time, I waited until Nancy finished getting into her tight dress and we departed for the lingerie shop. Nancy drove and recounted how much her client wanted to fuck her in front of me.
As we walked through the door of the shop, I was getting very nervous. A young blond named Crystal met us and smiled. The shop was very erotic with its dimmed lighting and many displays of elegant satin and lace. My pulse raced almost at once as my eyes feasted upon colorful bustiers, corsets, teddies and many more shimmering strappy articles. There were only a few customers left who were collecting their purchases.
“You must be Nancy and Jack.” Crystal said. “I was just about to close up, but the owner and I were expecting you and insisted we wait for you.”
“Thank you for doing this Crystal” Nancy said to her. “Is the owner here yet?”
“No, but it shouldn’t be long. The owner is very excited about seeing Jack and we both know how much you want to get JACK outfitted.” Crystal emphasized. The departing lady customers giggled as I got red-faced with embarrassment.
“Yes Crystal, he really wants to wear his own panties” Nancy said, smiling at me.
“Of course he does. He shouldn’t be wearing yours all the time. Look around and try on what you like Jack. I think you will be pleased with our very feminine selections. Don’t worry, you’ll be well taken care of here.” Crystal said to me. “And I’ll bet you like lots of satin and lace. Remember that special discount we discussed Nancy, I think we may be able to get that and maybe a little more.”
“Yes and I spoke to the owner about it today.” Answered Nancy
Nancy guided me toward the racks of beautiful panties. I was reluctant at first, but when I heard Crystal locking the front door, I calmed down a bit and started to fondle a pair of expensive shiny black brief style full cut panties. My pelvis stirring, I took them off the rack and then took off an equally gorgeous pink pair of the same brief style but with lace at the leg edges. Both pairs were so sexy and glossy, I couldn’t wait to wear them.
“Those pink ones are an adorable choice Jack, very pretty and they have a cute little bow on the waistband” Crystal remarked when she returned handing my wife a hosiery package and a set of shiny pads. “I thought you might want a pair of tights, for some coverage. And these shaper pads will give you a nice natural feminine form.” Crystal was rapidly becoming very helpful and so friendly.
“Great idea. Why don’t you go try them on.” Said Nancy, handing me the nude tights. “Go into the dressing room. You’ll need a few more pairs of panties for everyday wear and I want to pick out matching garter belts and stockings for you.”
I walked in the dressing room and closed the door. As I began to lock it, I heard Nancy say “Don’t lock it, we want to see. And I may need to help you with these garters.” She then handed me two enticing wide matching six strap garter belts for my panty selections along with stockings.
I undid and removed my pants and boxers. I saw Crystal and my wife pointing at my small penis already stiffening. Nancy grabbed up the clothes I removed. Leaving my shirt on, I then pulled the tights on and slid the pink shaper pads along my hips and rear end. Slowly, relishing the experience, I pulled the luscious new panties up my shaved nylon legs. I tried to do it just as a woman would. I wanted to savor the experience. Everything felt so wonderfully slippery and I enjoyed the sensation as I situated them around my stiffening little cock. I wanted to rub my erection, through the silkiness, so badly now. It was at that point to that I again noticed Crystal and my wife staring at me with a sly smile and crossed arms. I overheard the two remark about how much the store’s owner would enjoy a man in panties. Hastily, I grabbed the lacy pink garter and squirmed into the tight piece while turning myself toward the dressing room mirror to hide my excitement but also enjoy the view. I admired how the tights and pads accentuated my figure and flattened my pelvic area giving me a nice feminine look, just as Crystal had said.
“See Crystal, the panty fully covers his smallness with a satiny wrap.” Nancy teased. “Go ahead and pull the straps through your panties Jack, like I do.” Nancy commanded.
“I wear them the same way and yes, I see.” Said Crystal. “No wonder he enjoys lingerie so much. It probably feels much more comfortable for him to we
ar women’s items. They look great on him too.”
I did as told and pulle
d the front garters under my new panties while noticing the expensive price tag still affixed to the waistband. As I began to pull the side and back straps through and across my rear, I heard the shop door open. I was stunned for a second but I really didn’t care anymore that someone might see me. It must be the owner in any case. I felt so sensuous that I wanted to be seen. Unable to resist the sensation, I smoothed my hand across my pantied rear, for just a moment. It felt so slick and tight. It was euphoric feeling. When Nancy could see that I was finished she asked me to step out. I continued caressing myself until she curled her finger to beckon me forth.
I stepped out with my shirt somewhat covering my new panties and dangling garters. My wife stood holding a pair of beautiful tan silk stockings, pink spiked heels and a blond wig. Along side her was the ever-smiling and helpful Crystal. Also, there were now two gentlemen in the shop, one who was groping Nancy and the other who was staring quite intently at my silky pink pantied ass peeking from underneath my dress shirt. He gave me a long look up and down.
“That looks oh so good.” The staring one remarked. He was attractive I must admit. “You weren’t kidding Nancy. I’m glad you brought him to us.”
“You’re welcome. Jack put these pretty stockings on for him” Nancy told me, referring to the heels and stockings and wig.
“Oh yeah.” The staring man remarked. “I want to watch that.”
Deep in shame, I took the items and re-entered the dressing room. I sat down, in plain view of everyone and especially the staring gentleman and rolled up the first stocking in a slow deliberate manner.
“That’s it, darling.” My wife said. “They’re fine silk, you must be gentle. Roll them slowly and smooth them. These stockings are very delicate. Now let me help you with the garters.”
“Please, let me” said the staring gentlemen.
“Of course” Nancy answered. “So polite of you.”
Nancy dropped my strap and the man came to the dressing room.
“My name is Luke” he told me as he came into the dressing room. Kneeling, Luke rubbed the lacy top of my stocking. “I’m the owner of the store. Tell me, are you pleased with your selections? My we need to get rid of this” Luke said as he held the price tag affixed to my garter belt. Grasping my hip, he bit through the plastic tag holding the tag in place.
I don’t know what happened, but I was getting very turned on as he felt my knee and held my strap. My heart was pounding. I began to seductively roll the other stocking up my leg. Luke lifted the bottom of my shirt and attached the front garters for me. My stiff member jumped at his touch and Luke smiled as he saw it throb. He actually brushed it as he moved from one leg to the other.
“Yes, I like them very much.” I answered him.
“I can tell and I’m glad you like them. I don’t think we’ll need to worry about those prices either” Luke said eyeing my little cock. He held my hip and pulled the side garter straps and clipped them to my stockings. “I want all my customers to be satisfied. I haven’t had a crossdresser get dressed in the shop for me until now. By the way, those panties look very sexy on you. I like how you wear them over your garter belt. It’s very sexy and it turns me on very much.”
Luke almost whispered the last part in my ear as he squeezed my thigh before rising.
“Thank you.” I choked. “I do feel sexy in these things.”
“Stand up, so I can get your back straps… sexy” Luke said.
I rose and he got behind me, very close, and slowly pulled each strap down while I held up my stocking for him to attach. I couldn’t help poking my silken and nylon rear out for him a bit. Then I just had to bend over and smooth a stocking wrinkle at my ankle. Noticing my movement, Luke caressed my ass through the silky panty. For a moment I thought could feel a hardness against it as well. As he finished hooking my garters, Luke gave me a gentle squeeze on my pronounced ass. Then I stood and pulled the blond wig into place over my head before stepping into the pink heels.
“Very nice.” He said to me.
“Thank you” I said to Luke.
“You’ll need to do better than that” Nancy told me as she winked at Luke.
“Yes, you can do better, sexy” Luke agreed and pulled me close to him and firmly grabbed my rear with both hands. “Don’t you know that a good girl wears a slip.”
“Am I a good girl?” I inquired.
“You are right now” he replied. “But I think you want to a bad girl. Now lose that shirt and put on a camisole.”
My cock grew stiffer at his talk. Luke’s did to, I felt the rod as he pressed against me.
“I want you to pick out a pink bra and half slip and model it for me.” Luke told me. “The store is yours. You can repay me for it in a bit.”
Luke released his grip and I swished my hips and rubbed my ass for him over to a corner where the pretty slips were displayed. Finding a very short, lace trimmed pink one with a slit up the front, I bent over and pulled it on over my hips. More satin that made me feel so much sexier. And, it didn’t quite cover my stocking tops, even sexier I thought as I felt the metal garter tabs peeking out from underneath. Crystal had meanwhile followed me and chosen a matching pink bra, in 36C, to complete my look. Behind a rack of sleep shirts, I unbuttoned my shirt and donned my first bra. Crystal smiled at me as she softly inserted a large cool breastform into each lacy cup. She then helped me into a matching pink camisole.
“Let me put some pretty red lipstick and eye shadow on you honey” Crystal said. “Pucker up for me.”
I pouted my lips and closed my eyes as she painted my lips deep red.
“Oh, that feels good.” I said as the tube glided around my mouth.
“You look very sexy Jack. Just you wait for what feels good on your lips.” Crystal informed me. “You really look like you could use a dick in your mouth. And that feels oh so good.”
“Can I make a confession to you Crystal?” I asked.
“Of course,” She answered, starting to bush my eyelids. “Tell me anything honey. I’m here to help you through this.”
“I got very turned on by Luke’s touch when he fixed my stockings.” I told her.
“I could tell. Your little clitty is so hard. Very small but still very hard.” She told me, lifting the slip and rubbing the faint bulge therein. “I know he liked what he was doing too.”
“He felt me up.” I told her “It made me so horny. I thought I would pass out”
“I saw it.” She said. “I think you made him pretty horny as well. You do look like a sexy woman with that wig on by the way.”
“I think I want to suck his cock Crystal.” I admitted. “It’s all I can think about since he touched me. And I could feel it. Now I want to suck on it and even make it cum.”
“You would?” She smiled cocked her head and held my hand. “Is it your first time?”
“Yes it is” I acknowledged. “I think he’s got a big one so I’m a little scared but I’m also very excited by it. Oh, I just want to get his cock in my mouth.”
“I know you do and I think he would enjoy that very much. And since you’re wearing panties, it only seems proper that would want to suck a cock. You should suck cock. I bet you would be very good at it, especially on his. That’s what sissies do. In fact, I would guess that Luke is waiting for you in your dressing room. Why don’t you go and see if he’ll let you suck his. Remember, take it slow. And, here let me scent your intimates.” Crystal said as she squirted sweet perfume over all my silky items.
With my heart pounding and barely able to walk, I made my way back to the dressing room. Slowly I opened the door, revealing Luke, standing inside, pants removed. His fat beautiful cock hung there waiting. He smiled. I almost passed out again in anticipation of what I was getting ready to taste. My mouth hung agape. Casually, I got on my knees and came face to face with a real cock. I could feel the carpet pressing my silk stockings into my knees as I positioned myself between his legs.
“My you look even sexier. I love that slip and those b
ig tits.” Luke teased. “Can I call you Jaclyn?”
“Yes baby, call me Jaclyn, your l
ittle slut.” I responded and lightly felt his cock. “Please let me suck on this.” I begged as I touched his big cock, feeling it jump in my hand.
“I see you found a pretty a bra too.” He said as he rubbed the fabric over my legs. “You really want my cock don’t you.”
“Yes Luke. I want your cock in between my lips” I confessed. “And in my mouth.”
“Yes Jaclyn. Suck it for me. Suck it good.” Luke allowed. “Talk dirty though. Help harden it up for your sweet mouth.”
“Luke, it’s so big.” I began as I held it. “My, and it’s getting even bigger.”
“Does it make your panties wet?” He asked.
“Yes it does.” I replied, now stroking his shaft and licking my red lips. I wanted it so badly. “It makes them very wet. I think I may soak them.”
“Good. You’re a horny girl aren’t you?” he asked. “I want you to cum in your panties for me.”
“Oh baby it’s throbbing in my fingers.” I told him as the stiff rod pulsed in my hands.
“Are you going to suck it till I cum Jaclyn?” Luke asked. “Are you going to show me a mouthful of cum?”
It was all I could take. I answered with action. For the first time, I placed my mouth on a cock, a big one too. I let the head pass my lips gently and swirled my tongue around it. I had seen it done but I was doing it now and I loved it already. Luke’s warm thick cock tasted so good in my mouth. I grabbed the shaft at its base and let a little more slip into my mouth and then some more before coming back up along the underside with my bottom lip and starting the process over again. Up and down I went, trying to take more each time I went down. It got stiffer as it crowded my throat. It was huge. Getting bold, I went at Luke’s thick dick from the side and gave his balls a little tongue massage. Luke moaned and I knew I was performing well. Once I got back to a steady rhythm of bobbing up and down, Luke grabbed my new hair and pushed himself further into my throat, thoroughly fucking my face. I loved it. I could picture myself as the office slut. I thought about the fabulous lingerie adorning my body and the red lipstick smearing on the hard cock.
“Jaclyn, you are fantastic.” Luke groaned. “I think you’ve paid for your panties tonight.”
I moaned with my mouthful of cock. With more confidence, I sucked a bit faster and wrenched Luke’s now rock hard member in my hand. I was glad that I was wearing my feminine lingerie. I could feel every piece slipping around on my body and my garters tugged the stockings from underneath my lovely panties. As I steadily bobbed his cock against the back of my throat, Luke leaned over and slowly raised my short slip until it was hiked up to my belted waist. I knew if he felt my cock, it would explode. Instead, he placed a firm grip on my silky ass.
“Oh, oh Jaclyn, you wonderful little slut. I want you to work here in the shop, as a manager” He stuttered. “You really are doing so well. I’m going to cum baby. You’re going to make me cum.”
Pleased that I was going to make Luke cum, I lifted off of his cock and started to fast stroke it. Luke stood, knowing what I wanted. Still kneeling before him, I pointed the head into my waiting mouth. It came. First a thick, creamy, sweet load shot into my mouth, powerful and fast on my tongue. I kept stroking as juice continued to fill my able mouth. When I thought I could hold no more, Luke sweetly pointed his cock at me and squirted his remaining load all over my face. I swallowed the load and smiled in pleasure as the sticky goo covered me.
“Cum on me Luke. Please let me work here to, so I can wear lingerie and suck your cock every day.” I said as we both kept jerking it. I couldn’t believe how much he had. I was getting covered.
“You like that don’t you, you horny little panty slut. You are going to work here. You’ll dress very sexy for work and I promise you will get to suck many dicks.” He said through gasps.
Excited at my new job, I grabbed Luke’s cock and helped him in getting a few more nice squirts before finishing up. By now his cum was not only all over my face, but on my chest and lacy pink bra as well.
Luke caught his breath, smiled and guided me onto the sofa in the showroom and he left. When he returned, Luke was wearing a pair men’s black silk briefs. Very sexy for his big cock I thought. And, I couldn’t resist rubbing it through his brief. Smiling, he then reached under my slip and rubbed my clitty. Lifting my slip higher, he planted his swollen cock into my panited crotch and proceeded to drive his hips against my stiffy. I felt our silk underwear grinding against our hard cocks. Luke drove until my clitty spewed into my panty, which didn’t take long. I squealed as my climax came with intensity. It was my first panty fuck but I hoped not my last.
In my session of passion, I hadn’t noticed my wife left for the party and I didn’t care. After Luke finished doing me, I cleaned my spunky face and removed my pink lingerie. Crystal helped me change into my black ensemble. Again, Luke took pleasure in affixing my garters. Crystal applied my lipstick and helped me pick out a black satin sleep shirt and bra to wear out. Luke picked me out another short half slip in black this time. And I thanked Luke properly again, behind a rack of corsets. This time the blowjob lasted longer. After selecting a bustier, for me to wear, Luke then escorted me to the party after a wild ride in his car where he promised a nice long panty fuck on a bed while my wife watched us this time. These were the tricks Nancy played.