It Started With My Birthday

'Wow' I thought, did my dressing up drive her to this state? I should reconsider perhaps.

Meanwhile, I felt a warm mouth engulf my cock. I tried to see who it was but Kelly kept my face locked to her lips. I was responding and soon felt my cum boiling. In a few moments I erupted deep into that mouth as Kelly held my head and forced her tongue deeper. I was done with a massive orgasm that must have produced a mass of cum. Kelly noticed and slowed down.

"Like that?" she asked. I nodded breathlessly as the sucking continued cleaning up my shrinking cock. I saw Liza on her knees licking the last drops off. Jaz and Chrissie were in a lip lock of their own.

Kelly broke away and turned to Liza. Surprisingly she lifted her up, hugged her and gave her a deep kiss on the lips. For a girl that didn't like BJs and cum, she now tasted me through Liza's breath and mouth. I smiled. Perhaps she would change her mind about oral after all.

Jaz came over to me, gave me a quick peck on the lips, and pushed me down. I hesitated a second as she pushed me down to my knees. Liza & Kelly were still in a deep kiss, tongues entwined. Chrissy was feeling Liza's skirt and had freed her cock. I was about to taste a cock. It was at least 7", stiff, cut and pointed directly at my painted lips.

"Time to return the favor." Jaz pushed my head forward and I had no choice but to open my mouth. I tasted cock. Kelly had noticed me and stepped aside and decided to direct my head. I was now on all fours as I sucked Liza's hardness. Kelly made sure that my mouth went deep to the base of Liza's cock.

As I got into the rhythm, I could feel my skirt being raised and a lubed finger entered my virgin rosebud. I groaned with discomfort, but Kelly's hands didn't allow my mouth to break contact. Next, I knew I was to experience a tag-team approach. A cock entered my hole. It hurt but I was so aroused that my little cock was growing again. The cock pushed its way deep into my hole and fucked me in motion with my movements on Liza's cock. I felt Kelly release my head as I now had no choice. The thrusts from behind ensured I kept Liza's cock in my mouth.

I felt a hand on my cock, wanking it slowly. I responded of course. I hadn't come twice in a night in a long time. Suddenly, I felt a mouth on my cock, sucking it deep. My head was spinning with so many emotions. Every orifice was occupied. I felt tension building and the thrusts in my hole intensified. Liza too was increasing her thrusts and soon I felt a huge glob of cum hit the back of my throat. The movement in my behind intensified. The mouth on my cock was trying to separate my cock from my body. I came in an intense gush at the same time as the cock in my hole finished. I was spent. My mouth was sore and my behind too. I had received two BJs and as I moved away from Liza I saw that it was Kelly's mouth on my cock. A little cum was dripping down her mouth. I looked at her unsure of what this was all about. It seemed that Jaz had been at my behind.

"Happy birthday," Kelly said as he kissed me hard and passing my own cum back to me. I didn't care. It seemed this would be the best birthday ever. "I think we'll do this again soon," she said as she gave my cock a little pull and tucked it back into my pants.

Meanwhile, it seemed that the only one left out was Chrissy. Jaz was now paying attention to her. I saw Jaz take her deep into her mouth and stroke her balls. It didn't take long before Chrissy blew her load into Jaz's mouth.

Jaz stood up, came to me and thrust her cum coated tongue into my mouth. She passed all of Chrissy's juice to me. I had tasted Liza's, my own and now Chrissy's. I enjoyed them all.

"Ready to go home?" Kelly asked. I nodded. Liza and Jaz sat me down and fixed my smeared makeup. They replaced the big bouffant wig with a natural-looking shoulder-length auburn wig. A more modest skirt and a large scarf for my shoulders.

"Keep the outfit," Jaz said. "But see you here next week in drag." They kissed me on both cheeks, gave me a big hug, and wished me again. I saw Jaz give Kelly a bag. "For later," she whispered.

Kelly and I left the club, hailed a cab and got in. It was almost 3 am. We were home in 10 minutes. We staggered into the apartment. I was glad that nobody could see me. At this time of night, the elevators were empty.

"What's in the bag?" I asked as we entered the apartment.

"Sorry, need the bathroom," Kelly said and rushed away. I needed something long and cold and went to the small kitchen.

Kelly returned and also asked for a drink. I noticed the bag was missing. Kelly sat on a barstool in our kitchenette drinking Perrier. Curiosity got the better of me.

"So what was in the bag?" I asked moving toward her. I owed her. She had accepted me in a dress and had even sucked me off without asking. It has been fabulous. So many emotions. "Did you enjoy yourself tonight? Not grossed out at how I look?" I hugged her from behind and noticed my breasts pushing into her back.

"Actually, I didn't at first. But seeing all the other 'ladies' out there and you in that outfit really turned me on. I loved seeing Roxy with a cock in her mouth. That turned me on so much I had to suck you. Did you enjoy your birthday?"

"It was fabulous. I never expected it to end like that. I will never forget this." I tried to muzzle her neck but the chandelier earrings kept me from good access.

She turned to me and grabbed my cock through the short skirt. It was still soft. "The night isn't over yet. I need some relief too." She pushed me down, wanting oral I guessed. I realized she hadn't had much relief at all till now. "We'll have to get you some new outfits and makeup. I think I like my new girlfriend."

On my knees, I lifted her skirt and it hit me in the face. She had a massive cock extending from her vagina. This was Jaz's gift to her.

"Now blow me, bitch! Your arse is mine, baby" She thrust the monster into my mouth. I was sure she was going to spear me again tonight at both ends. I sucked hard. They say 'practice makes perfect, right?'

What a birthday bash and a new life in a dress with exciting possibilities stood before me.

After that big birthday party, Kelly had me stay dressed all Sunday. She had used her strap on at both ends that night and on Sunday night, before I had to get changed, she allowed me to enter her. We both collapsed in a heap and swore that we would repeat this soon. Kelly, crawled down my body, trailing kisses from lips to neck, taking a nipple into her mouth and finally engulfing my limp tool, covered in her juices. A few minutes of gentle sucking and my reaction began. Soon, it was rock hard and Kelly kept up her rhythm, going deep and taking my cock almost entirely down her throat. This for a girl who had refused to blow me for so long was an amazing change. Finally, I held her head and thrust into her mouth as Kelly sucked me clean until I was limp again. She crawled up again, and nipple to nipple, kissed me fully with tongue passing on whatever I had ejaculated. We swapped juice until our lips were sore. A glorious end to a fabulous birthday weekend.

We had promised Jaz to visit again next Saturday. It had been a wild weekend full of firsts. But I also knew that I was hooked. Seeing Kelly's reaction, I knew we would develop this further. I was surprised how she had warmed up to see me in drag. Now, she was also hooked it seemed. What lay in the future?

The workweek started. Kelly had said she needed to go shopping and she wanted to do this by herself. She came in a couple of nights with bags of stuff that she hid in the closet. I wasn't to look. She had a sly smile on her face as she tempted me with what might be in the packages.

All she would say is that it was for "Roxy".

During that week sex was fantastic. We seemed to have reached new levels of intensity and intimacy. She did go down on me every time as foreplay but insisted I enter her to finish. I was happy to get some action and we also did a 69 once. She was getting very much into it. Saturday was the day we had planned to go to see Jaz.

On Friday Kelly asked me to come home early as there were some preparations to make. She had me take a shower after applying some cream all over my body, even between my ass cheeks. She was careful about the pubic hair in front. As could be expected, her playing with my privates forced an erection. It got so hard that she relented and took me in her mouth. It wasn't long before I blew a load into her which she happily swallowed. I still wondered at that and what had changed her mind.

I showered and saw all my hair disappear down the drain. My legs and body felt smooth and I loved the soft touch of fabric on my skin. After toweling dry, Kelly ribbed cream all over me and that felt even better. Then, to the serious stuff. She led me to the bedroom where she had laid out all that we might need.

She started with a corset. Although I was in pretty good shape, I didn't have the figure of a woman. The corset changed that to give me a slim waist. It was tight but manageable. Then she hooked a bra on me and stuffed the cups with the inserts that Roxy had given me. They appeared much bigger given my slimmer waist. A garter belt was next and she rolled up some beautiful silken stockings and attached them to the garters. A really tiny, bright red panty came next. My member tried to get a lift from all the touching but Kelly tucked it away tightly between my legs. A very short mini in black leather barely covered my stocking tops. She had me try on a pink short-sleeved blouse which she buttoned up from the bottom, leaving the top buttons undone and showing my busty cleavage. A broad black belt tightly cinched above my hips completed the outfit. Only the shoes, wig and makeup remained. The heels were spiky and 5" tall. I wasn't sure I could stand in them let alone walk in them.

"Well, what do you think?" Kelly was studying my figure. "A lot more to do tomorrow but I like the way the figure is shaping. Jaz will love you." Kelly winked. "Enough for today, big boy, tomorrow will be a big day for you. We need to get some rest." I started to undress. Sex tonight seemed out of the question.

I woke up late on Saturday and went out for brunch with Kelly. She didn't say much except that we had to be back by 2.30 pm or so. "Why so early?" I asked. "Surely we are not leaving till about 8? Right?"

"Yes, I made a reservation for 8 pm, but it will take time to get ready. I have asked Jen, my beautician, to help"

"Whaaat," I stammered. "Why? We don't need her and I'd rather she not see me dressed."

"Use your big head for thinking, Kev. Everybody is going to see 'Roxy' tonight. So what's the difference? Besides, I told her all about last weekend and what a blast we had. She was jealous."

This was getting a little out of hand. But how to control it? But Kelly was right. Tonight I would be on show and I was going to enjoy it. I was thinking back to last week and how it changed me - and Kelly... all those enthusiastic BJs. Well, tonight would only make it better.

We got home and Kelly had pushed me into the shower, lathering me from the chin down with some cream. She was careful to avoid the pubes but made sure it was rubbed in between my cheeks. I knew this was hair remover and waited for it to work. I got into the shower and saw the hair wash away. I took a double shave and was ready.

Kelly was waiting. "OK, Roxy, time for your transformation. Lie down on the bed." I wasn't sure what was next but lay down. Kelly approached with some objects in her hand.

"Lie still now and hold these tight to you for a few minutes." She placed two large jelly-like objects on my chest, centered over my nipples, and pressed around the edges. I now had two realistic breasts. "Not cheap but look pretty real. Jaz thought you should get a big rack."

Kelly smiled at me. As I stood up I could feel the weight. It seemed like size 38 D or even DD. Kelly held out a bra and pushed through my arms and attached the ends at the back. The bra was low cut and showed a lot of cleavage. Kelly pinched the oversized nipples and I thought I felt something. She adjusted the bra, tightened the straps and I felt less weight.

She held out a short waist cincher, attached the hooks in front and tightened the laces at the back. I could feel my whole stomach drawn in. Whilst giving me a great shape it also pushed out my breasts more prominently. I was certainly stacked. A garter belt with six tabs held up the black mesh pattern stockings. They highlighted my smooth legs. A black thong panty was drawn up my legs. My dick was now standing proud, in complete contrast to the female shape that was forming. Kelly grabbed my shaft in one hand and my sac with the other.

"Looks like someone is having a lot of fun." She was smiling as she slowly stroked me. "Does Roxy like being a girl?" She pulled me to her by my cock and kissed me hungrily. I responded in kind. "I know what you like," she breathed as we ended the kiss and she sank to her knees. Her mouth swallowed me in one swoop. Where was that girl that refused to blow me last week? I let her tongue do the talking and soon she had my sac in her mouth. I nearly fainted. She took me in her mouth again and with both hands now around my buttocks, pulled me deep into her mouth. I was done and came in a huge gush. She held me in her mouth, shaking her head to shake off the last drops and stood up. She pulled my head to her and gave me a tongue kiss and passed on a good bit of cum. I was so excited I accepted it and mashed my lips against hers.

"Enough play. Still, lots to do she said." The silver top with flared sleeves was next and she pulled up that miniskirt. I was a figure to behold. No makeup or wig, but from the neck down I looked hot.

"OK, now step into these heels." She held out two silver heels with probably 4" or 5" spikes. I slipped them on. Tight but manageable. As I stood up I was over 6 ft. tall. It took a few moments to get my bearings but relaxed. "OK, now come behind this chair and bend over. I need to check something." I turned around, sideways to the mirror, and bent across the back, lifting by behind. Kelly was rummaging around and came up behind and slid my skirt up a few inches. It was so short anyway; it was almost at my waist. Her cool hands felt my cheeks and soon I felt some slippery finger enter my behind. I hadn't been penetrated by her in a few days now and moved in rhythm to her fingers. Two, then three fingers pushed lubricant deep into my rectum. Just as I was enjoying this, her fingers withdrew and I felt a sharp thrust in my behind. I thought it was her strap on. But discovered it was a fat plug. The base was flush with my hole, the shaft buried deep as far as it could go. "Just want to make sure you won't be too sore for later." Kelly winked at me as she stood me up and smoothed out my skirt.

"Sit, Roxy. Just a few things more." She pushed me down gently and I felt the full length of the plug settle down. Some glittery hanging earrings were clipped on. "Don't need a lot of makeup as Jen will fix all of that."

"What time is she coming over?" I asked. "She's not coming here; we're going to the salon. What did you think? She would give up her Saturday afternoon to come here?"

"Noooo, Kelly, we don't need her. You can do it. I know you can." I was whimpering now not wanting to walk into a salon and be read. She brushed some powder, some light eye shadow and then painted my lips. 'That'll do till we get there."

I looked at myself apprehensively in the mirror, still not sure that I would pass in broad daylight. Without the wig, my made-up face and big bust reflected a curious male-female, more in keeping with some fantasy event or even Halloween.

Kelly brought out a box and out came a wig. Blonde, shoulder-length. She placed it on my head and brushed it out. This made all the difference. Whilst not a stunner, I would pass. Kelly gave me a small purse and I stood up, mesmerized by the image in the mirror. I was excited by the thoughts of tonight. How could we top last weekend's birthday bash? And Kelly, from shy lady in the bedroom to an aggressive cocksucker. I was on a high...then my elation died. Thoughts of where this would end...

"Kelly," I asked, "are you OK with all of this...? I mean I love that we can share this but I don't want to force you into anything. Really..."

"Kev, Roxy, we've known each other for more than two years now. Have you seen me do anything I don't want? Not sure myself, but seeing you in that outfit, turned me on as did the sight of you with a cock in your mouth. As you may have noticed my own interest in that area has grown. Let's just enjoy..." Kelly gave me an air kiss, a pat on my backside and ushered me out of the apartment. It was around 3 pm when we got to the salon. I stepped out of the car nervously. I wasn't sure what lay ahead. Kelly grabbed my elbow and off we marched to Jen's salon.

Jen's salon was a small and busy salon. Several ladies sat in the waiting area and a couple under dryers. My first encounter with a stranger dressed as Roxy. Thankfully, Kelly did the talking and soon Jen herself appeared. She was a buxom girl with a big smile. She welcomed Jen with a hug, gave me a kiss on the cheek and welcomed me back.

"So, let's use the private room at the back," she said and led us through a heavy curtain to a small room at the side." OK, take off the blouse, bra, and skirt and we'll get started."

"Can I talk to you Jen?" Kelly asked. "Roxy is quite nervous and I want to make sure she is going to be happy with the changes." I stood there silent as Jen led Kelly outside the room and I undid the belt and did as Jen asked.

Some 10 mins later Jen and Kelly reappeared smiling. "Lots to get done," Jen said. "Give me a couple of hours to do my stuff."

Kelly looked at me standing there in a bra, corset and stockings. "OK, Kevin, I mean Roxy, be a good girl and trust Jen, OK? I've got to pick up some things and will be back in a little while." I just nodded.

"Let's see what we have here," Jen said as she inspected my figure. "I think we'll take the corset off for now. Easy to re-attach later. I love that rack of yours. Looks natural to me. Kelly did a good job fixing the forms, but we may have to adjust." She stroked my breast sensuously and gently tweaked my nipple. Was this my imagination?

"Lie back in the chair." Jen pointed at a chair that seemed to be adjustable. I sat down and felt myself sink in. I could easily have taken a nap. "I know what Kelly wants, OK, so I am going to use these straps so you don't move suddenly." I just nodded, not really absorbing what she was saying. Jen adjusted the chair so I was almost horizontal. She had padded straps to secure my arms and legs. She removed my wig and earrings and must have looked quite a sight.

I felt a moist warm towel placed on my face and a few minutes later I felt wet flannels remove all the makeup Kelly had previously applied. It wasn't as heavy as when Jaz had done it. I closed my eyes and tried to relax wondering how I would look. I felt Jen run her fingers across my chin and upper lip. "Think we need to give you a closer shave to avoid that five o'clock shadow."

Jen applied lots of warm foam to me face and I saw a cut-throat razor in her hands." Don't worry; I know how to use this." She began to give me a close shave. I could feel the sharpness of the blade. A warm towel wiped off all excess. I was beginning to enjoy this. I felt fingers trace my eyebrows. "Have to trim these a little," she said. .'Oh oh,' I thought. How would I look on Monday at work? I felt something warm on my eyebrow and before I knew anything, I felt a searing pain on my brow.

"What are you doing?" I asked sheepishly. "I have to go to work Monday."

"Don't be a baby," Jen said. "This grows back soon and nobody will notice. Tell them you have some eye issues and wear some sunglasses." In the next few minutes more strips were attached and peeled off. It stung a lot.