The Box

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She climbed down and asked "Do you want a safe word?" and my answer was "I trust you so I don't think I need one." She smiled and asked me to pull down on my arms to see if the straps were secure, so I did, and they held. "I don't think I'm going anywhere" I said, "not that I want to anyway."

Renee laughed.

"To answer the question, yes, seeing you dressed turns me on. Seeing you in lingerie turns me on. Seeing you tied up standing REALLY turns me on" Renee offered, and then put her fingers on my lips again to keep me quiet and asked me "Does dressing up turn you on? Do you like turning yourself into a girl? Does getting ordered to obey turn you on?" and then Renee reached into the g-string and felt me and said "I think I have my answer" and my only response was a long groan, as I had waited ten days for a release, which I hoped was coming soon.

She repositioned the step-stool in front of me so the steps were facing away and sat on the stool. I looked down in the candle light to see her reach with both hands and pull down the g-string and my penis popped up, semi-erect. She looked up, saw me watching, smiled, and then softly grabbed my balls with the right hand and the shaft of my penis with her left, opened her mouth, and inhaled me. I became stiff immediately. She dampened my shaft with her saliva, pulled her mouth back a bit, and began to tug my shaft with her left hand. The sensations left me squirming, standing in heels, back against the door, with my arms tied in the air. I was at Renee's mercy, grunting in pleasure.

Her mouth went down on me again. I'm not sure whether she was teasing herself or teasing me, because she seemed to want it as badly as I did, but didn't want it to happen too quickly. Suck, then tug, suck, then tug. My knees were getting wobbly and I was getting close.

Sensing this, Renee took her right hand off my balls and reached up and stuck her index finger in my mouth. I sucked on it like she was sucking on me, then quickly removed her finger and immediately stuck the finger up my ass.

I exploded. I grunted, I groaned. I felt five or six blasts--I lost count--of cum into Renee's mouth. I could hear her grunting too while her head bobbed back and forth, taking all that I shot out. My legs shook, my arms jerked against the straps, and I felt my whole body vibrate in pleasure.

A few seconds after I stopped firing, Renee pulled her mouth off my cock and said "Happy birthday." I merely said, "Well that was better than cake and ice cream."

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Renee stood and reached for the closet door knob and rotated the knob so the door opened. When the door opened the straps fell slack and I was able to drop my arms to my side. She faced me and gave me a big kiss, and smirked "My turn for cake and ice cream" and grabbed the free ends of the two straps, turned and led me to her bed. She pulled back the blankets and top sheet and told me "On your back in the middle of the bed" and I did as requested.

She climbed on the bed after me and crawled to the right side of the bed, took the free end of the strap, stretched my left arm out, and tied the strap to one of the rails on her headboard. She then climbed over my chest to the left side of the bed and did the same with my right arm. Once again tied up, this time horizontally instead of vertically.

"Still ok?" she asked and I answered "I'm more than ok" and then climbed on top of my chest with her knees straddling my ribs. She leaned down and kissed me again and while kissing me she reached under the baby doll and bra with both hands and tweaked both my nipples. Once again she had me groaning, this time a combination of pain and pleasure.

She then placed her palms on my chest, pushed, and stood up on the bed with her feet on either side of me. She took her hands and grabbed both sides of her shorts, then pulled them down her legs, first raising her right leg to free the right side of her shorts, then repeating the action with her left leg. As she wasn't wearing any panties, Renee was now naked from the waist down. She took one step forward, right leg, then left leg, then began dropping to her knees, now straddling my upper torso.

Her pussy was now inches from my mouth. She then inched forward until her snatch could be reached by my tongue. She reached forward with her hands to rest on the headboard, allowing me better access. I knew what she wanted, but in case I didn't, she commanded me to "Make me cum with your tongue."

With my hands tied it was somewhat difficult to get the right angle, but Renee helped by subtly adjusting her vagina to allow me better access. I did my best to pleasure her and it was her turn to begin squirming and grinding her crotch into my face. After a few minutes, she reached to the left and grabbed something--and a few seconds later I heard a click and then a buzzing sound. She repositioned herself so I could lick her again, and then lowered the vibrator to her mons.

I could feel the vibrations on my tongue and between me and the machine--mostly the machine, I'm sure--it was Renee's turn to start moaning. I redoubled my efforts and it seemed Renee began pressing the vibrator harder against her crotch. She began shaking and then started yelling "oh" in a loud voice and after about ten seconds moved the vibrator away from her crotch and partially collapsed on top of me. After a short rest to catch her breath, she leaned down to kiss me again and then said "Good girl."

Once again she stood up, and turned 180 degrees so her derriere was now facing me. She lowered herself again, orientating her pussy to my face again, but now reaching for my penis so we could sixty-nine. I began to lick her and she began to blow me. I could feel myself starting to harden again and was enthusiastically tonguing her clit to help her get off again.

But Renee had other ideas. Once she got me hard, she quickly did another 180 and lowered her slit to engulf my penis. She leaned forward and said "I enjoy sixty-nine but I love getting fucked" and I was too busy thrusting to answer. She grabbed the vibtator again, turned it on, and placed it between our crotches and leaned forward to kiss me again while the vibrator worked on both of our nether regions. I was bucking against her and the ties that held my arms until we simultaneously both exploded with our own orgasms.

She rested on my chest for about a minute while we each caught our breath. She then kissed me, and reached to my right arm to untie my wrist, and then the left. With my arms free I was able to reach around her and give her a big hug while saying "Still

better than cake and ice cream."

Renee just laughed.

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When we woke in the morning we had another go, this time less frantic and me on top in the missionary position. Following our adventures the night before, we both dozed off. I woke up about an hour later needing to pee and stripped and took a quick shower to remove the makeup, with the boy me returning to bed. Renee cozied up to me and we both slept peacefully. After our morning fun, Renee teased me "Just wanted to prove to you the boy you is a turn-on too, plus you need a final birthday present."

She offered to make breakfast but I declined, as I was going to do my morning run in Forest Park before driving home, a change of pace from my normal route. I changed into my running clothes that I had in my overnight bag, stuffed my girl stuff into the bag, and left Pete's wig with Renee. We agreed to meet in a week or so after Renee had processed the photos.

While I ran the five miles circling the park my thoughts alternated between when I might be able to dress again--and what lie I was going to tell mom about what I had done the night before when I went to my parent's house that afternoon.

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Renee's corporate clone duties kept her out of town for two weeks. On her return, we agreed to meet for drinks after work on Friday. Because she had been on the road and needed rest, she said she was going to need to keep it short.

We met at a downtown bar at 6:30, although she was a few minutes late. We hugged and found an empty booth and sat, and after the waitress came for our drink orders, she pulled the envelope of photos out of her purse. Some of the pictures turned out better than others, and in a couple, both in the dress and in the babydoll, I looked pretty good and perhaps even sexy. Renee asked to keep a couple of the photos and as I had plenty, I was happy to agree.

After we had finished with the photos Renee looked me in the eye and said "There's another reason I sent you the box, besides that I was curious and turned on by seeing you dressed. I've been seeing someone else and we are getting serious. We've decided to become exclusive, but John said I could have one last night with you, and I wanted to make it memorable for both of us. I thought I owed it to you for being a friend and a lot of fun. Not exactly a 'hall pass', but he didn't want to know the details. I didn't want to tell you that night but I also owed it to you to tell you face-to-face, so I'm here now."

I was surprised by Renee's admission but not shocked. We had fun together--and some good sex--but definitely weren't in love. "If you've found someone who makes you happy, I'm happy for you" I said. "Plus, this is probably the nicest way I've been dumped in my dating career" I added and she just laughed. I picked up my beer and toasted "To future happiness" and Renee did the same. She had to run so we hugged and I took my photos and memories and headed home.

During the drive home, the chorus of a favorite Richard Thompson song called "I Misunderstood" echoed in my brain:

"But I misunderstood,

But I misunderstood,

But I misunderstood

I thought she was saying good luck,

She was saying goodbye"

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Over the next couple of years Renee and I talked a few times on the phone but didn't meet in person. Then one evening in the spring she called and wanted to get a drink. She had news to share. John was finishing his Ph. D studies in political science and found a tenure track position at the University of North Carolina, and Renee was planning to move with him to the Raleigh/Durham area. She said she also had other news to share, but wanted to do that in person--plus she wanted to see me again before she left. We agreed on a place and time; a Thursday night at 7 PM, at an upscale bar in an upscale hotel in mid-city.

I was sitting at the bar nursing my drink when Renee arrived. I spotted her first and gave a slight wave, and she walked over, in a business suit and skirt, one of her corporate clone outfits.

"I didn't recognize you, but I recognized the dress," said Renee.

I stood in my heels--the same ones Renee had bought me--and gave her a hug, and she reciprocated.

She took a step back and gave me the once over. As always, she said "Turn around" and I did so, and when I turned around to face her she said "you look really good."

I answered "Thanks" and picked up my wine glass from the bar and said "let's find a booth." We waited at the bar while Renee ordered and paid for her martini, and then strolled to a row of booths, with me in the lead. I think Renee wanted to watch me walk in heels.

As she sat, I saw the ring on her finger and asked "Are congratulations in order?"

Renee answered "I guess so" and then went on to explain that she and John had been discussing marriage for a couple months, and had decided yes a couple of weeks ago. They didn't have a date, but it would likely be a while before they actually tied the knot. She told me to expect an invitation, and she said with a smirk, "I already know your address."

I told her "You look happy" and she said she was. She then added that once they got to Carolina she was going to get a masters in education, stop being a corporate clone, and become a teacher, preferably an elementary school teacher. The move was a good time to make the change and get out of the rat race. It would mean less money, but more happiness. I simply answered, "I'm happy for you."

She then reached into her purse and pulled out a small wrapped package and handed it to me, with the words "Open it."

I unwrapped the package, and extracted two ties, and was about to ask why--but then laughed when I realized they were the ties Renee had used to bind me our last night together.

"I figured you might want something to remember me by," said Renee with a smile.

"You mean besides the dress?" I answered Renee with a question. That morning when I was returning Pete's stuff, I tried to give Renee the dress back, but she said "No, keep it. It looks great on you and I want you to have it" and I was very happy to keep it so I didn't argue.

"Well, I figured you could wear the ties at work and I don't see you wearing the dress to work--at least not in the near future" Renee added. "The ties will be our secret."

"I will wear them proudly," I said.

Renee then said "Let's talk about you. Spill."

i did a brief recap, about work (boring), dating (nothing happening), and dressing, to which Renee perked up. She wanted to hear everything.

I explained "As Halloween was a few weeks after our last date, I decided to go bold. I went to a costume shop and found a Dorothy costume (from the Wizard of Oz), and found a friendly wig shop, and bought this wig. I found some red heels at Payless and went to a Halloween street party in the Central West End." Then I smiled and added "I even came in here and ordered a whisky sour, and made a toast to you."

Renee laughed and said "Great!"

I went on. "I spent about four hours walking around, loving the idea of being out dressed. I decided I didn't want to wait another year for Halloween to do it again. A couple of weeks later I saw an ad in the RFT for a group dedicated to crossdressers. It took me about a month to work up the courage to contact them, but eventually I did and joined."

"Good for you," said Renee.

"I began to go to the monthly meetings. I met others, learned from them places to shop and where to go. I began to shop at thrift stores and use holidays like Christmas and Valentines Day to expand my wardrobe. I found places to change, like the family room at the downtown YMCA" I added. "Like tonight. It's fun, although a bit nerve-wracking, to walk out as a guy in a suit and walk out as a girl in a dress."

"You mean STRUT out as a girl in a dress" Renee interjected. "How often do you go out?"

"Two or three times a month, usually one of our group dinner meetings and one or two other outings" I answered.

"Well you look great. Your makeup looks great. The wig is a great color and frames your face nicely. Your accessories are spot on. And....your legs are still fabulous" Renee beamed.

"Thanks. I'm glad you like my look. You gave me the kick start to get out and dress up, and getting out now and again does make me happy" I said.

"It shows" Renee responded "in your Mona Lisa smile."

That comment left me smiling.

"Do you have a femme name?" Renee asked.

"Dee" I answered, then added "it just seemed to work".

Renee finished her drink and said she had to go, that she was meeting John for a late dinner. She then added, "I hope we can stay in touch. I will be sending you a wedding invitation. You can decide whether you want to come as Dave or as Dee. I think you know which one I would prefer."

We both stood and hugged. "I guess you know you were my second favorite response to my personal ad" Renee said. "And I would have never guessed one of my favorite dates looked so damn good in a dress."

All I could say was "It's a great looking dress. See you, Renee."

"See you, Dee" Renee replied back as she walked out of the bar.

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I ordered a second wine and an appetizer as I pondered what to do with the rest of my evening. I decided I wasn't in a hurry to do anything.

I sat and sipped and nibbled and reflected on the events that had led me here, sitting in a booth in a bar, a guy in a dress, a damn cute dress.

Why I answered Renee's ad, I couldn't remember. But it had led to our meeting, and the box, which I finally understood was Renee's gift to me, to force me out of my comfort zone. She knew that she was moving on, but she wanted to leave me better off than when we had met, and she did.

Renee received her own reward. Ironically, she placed the ad because she had a coupon for a free ad. While my response was in the first batch of letters, John's was in the third. Renee cast her bread upon the water, and was rewarded with her lifetime mate.

She stepped out of her own comfort zone, and found her own Mona Lisa smile.

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3 Comments
AnonymousAnonymousover 1 year ago

Kind of reminds me when I started dressing. I love sexy lingerie & high heels. I always imagined going out in public & meeting a man to accept me.

AnonymousAnonymousover 1 year ago

Beautiful CD story; unspoiled by Violent sex, futas, 14" dicks and other cruelty. I really enjoyed it

tonitemptstonitemptsover 1 year ago

That was fantastic. I absolutely loved it. Thank you so much for sharing that!

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