The Path to Happiness Pt. 03

I woke from a blissful slumber to the smell of coffee. I was grateful for the sofa that acted as my bed in my squat, but this bed was so comfortable I did not want to get up. As my senses returned to me, I noticed my arse was a little sore, Becky's cock cage would need more lube than a little spit if it was to go back in me.

I slipped reluctantly out of the bed and pulled on a robe. On the table was a fresh pot of coffee, I sat at the table and poured myself a mug and stared out the window at the grounds of the hotel. In the distance there were a few men in bright pringle clothes playing golf, off to the left was a large lake with several lycra covered runners out for an early morning jog. The bathroom door opened and Roger strolled in freshly showered with just a towel around his waist.

He joined me for coffee and we discussed the previous night's activates. I explained that more lube would be needed if that cage was to enter me again, he apologised and said he had some in Becky's bag.

We chatted about Becky, she emerged shortly after Roger's accident. Word of his injury got out at school and he was teased that he was no longer a man. One day a group of kids cornered him and stripped him and stuck him in a dress. His parents moved him to another school, and things got better for him. But it was over that summer break that he started to explore his female side and Becky was born.

A girlfriend in college who was understanding about his condition, help bring out the true Becky. She taught Becky how to dress and act like a woman, she also introduced Becky to anal sex. Shortly after they broke up but remained friends, she introduced Becky to her first boyfriend. She dated Kyle for just over year, but Becky was in the closet. She would only come out to play in the privacy of her room or if they travelled away and stayed in a hotel. Becky revelled in those weekends she could be herself.

Unfortunately, Kyle bored of the part-time girlfriend and dumped her at the end of college. Since then Becky had not come out to play very often in public, and she has had only a handful partners.

We dressed in some casual clothes and headed down for breakfast. I noticed several of the other wedding guests tucking into their fried breakfasts. I only indulged in some cereal and toast, whereas Roger had the works.

I sat drinking my orange juice Sylvia, Chris's wish rushed in and scanned the room. She then made a beeline to our table, and I had a sudden fear of panic that she had found out what her husband and I had gotten up to! She slid into the spare seat and turned to me. It turned out that one of the bridesmaid's parents fell ill last night and she had to leave. I was a similar size so would I mind standing in for her. I was in a daze, but agreed to do it; and 10 minutes later I had my instruction. I was to go with her to collect my dress and accessories, then the makeup girl would come to my room. When I was ready, I had to report to the to the bridal suite ready for my duties.

We swung by Sylvia's room where she loaded me down in with bags, Chris was already in his morning suit and winked at me when his wife was not looking.

The dress was off the shoulders, but luckily, they had included underwear in the bag, so I had a strapless bra.

Back in my room, I hit the shower and gave myself and going over with a razor. My dress was a full-length turquoise gown, with matching 3"-inch heels. It also came with a white bra, panty and garter belt; with tan stockings. I stuck on my breast forms and pulled on my gaff and started to dress. At the bottom of the bag was a neckless and ear rings, luckily, they were clip-on ear rings. Note to self, time to get my ears pierced.

There was a knock at the door as I finished gluing my wig back on. It was the makeup girl; she was a friendly and quickly identified my true gender; but she said it was cool and could make me beautiful and my secret was safe with her.

For the next half hour, she teased my wig and made up my face and gave me many great tips. After she was done, I looked in the mirror and she had brought out my cheekbones and rounded my features. I thanked her and she left.

Roger returned and told me he was jealous, but I was beautiful; I blushed.

I gathered my belongings into my clutch purse and headed to the bridal suite.

I knocked on the door, and a girl dressed identical to me answered. She introduced herself as Jen, as she held out her hand in greeting. Immediately a glass of champagne was thrust into my hand as I was swept up in commotion of the wedding preparation.

Jen introduced me to the other two bridesmaid's Clare and Sarah. In the corner Alison was being helped into her white dress, she turned her head and thanked me for stepping in.

The next hour flew by and the next thing I knew it I had downed two glasses champagne; I was a little giddy. Chris arrived and gave me a wink, and out of earshot of the others commented I looked hot. He said perhaps we could have a private moment later that day, I said perhaps we could arrange something.

Sylvia arranged us in to our positions, Chris and Alison at front, Jen and Claire next, with Sarah and I bringing up the rear. My clutch purse hung from my left wrist and bouquet of flowers to hold, we marched out the door.

We reformed in out order just outside the marque in the grounds of the hotel. Sylvia wished us good luck and gave Chris and Alison a quick peck on the cheeks, and then headed in to the tent. Alison turned to us and thanked us again as the wedding march started up in the tent.

Slowly we started to walk in unison toward the alter.

45 minutes later, Mark and Alison were married, and we had taken what felt like 100 photos. I managed to finally catch up with Roger and we slipped back into role of a loving couple. As the day wore on, I was comfortable with the extra attention I got from my bridesmaid duties. After the wedding breakfast my duties were done.

I stepped out into the garden for a breath of fresh air when Chris came out. And came up to me, he asked me if I was free for a little father of the bride relief. I took his hand and lead it off to some bushes out of sight of everyone and opened his dress trousers and took him in my mouth. He closed his eyes as I worked his shaft with my hand and mouth, his moaning was becoming a little loud so I increased my pace to bring him to climax fast. I tickled his balls and that did it as he blew into my mouth.

I cleaned his cock and stuffed it away, zipping him up. As we strolled back to the wedding, I suddenly dropped the bombshell that I would be leaving town in a couple of weeks. Chris was a little shocked, and said this was sad, he would miss my sissy arse. It quickly dawned on me that I could help out two of my "clients" at once. I told Chris to come to Roger and I's room tonight.

I re-joined Roger and at 10pm I asked Roger if we could leave. He agreed and we said our goodbyes and I whispered to Chris to come to our room in an hour.

Back in our room I told Roger I had a surprised I arranged for Becky. Roger rushed off to the shower. I slipped out of my dress and I slipped into a blouse and skirt. Becky came out of the bathroom 20 minutes later dressed in her sexy night gown. Becky looked at my confused at my conservative attire and I told her I had an alterative outfit for her.

I took off her nightgown and started to pull items out of my bag. I slipped a white blouse up her arms and fastened the buttons to the collar; I had her next step into my grey box pleat skit. I lifted the collar and slipped the blue and gold tie around her neck and tied a full Windsor knot, the point of the tie fell perfectly on the waist band of the skirt.

I topped the outfit off with the grey pullover with black and gold trim, and the blue blazer, again with blue and gold trim.

I rearranged her hair into pleated pigtails, she looked like a perfect schoolgirl. I handed her a glass of wine and explained we were having a guest.

There was a knock at the door and I let Chris in, I immediately fell into character. I said "Mr Harris, Becky here has been caught flashing knickers at boys in the class". For a moment Chris looked confused but seeing Becky standing a little scared in her uniform realised what was happening. Thank you, Miss Chaplin, he said as he walked around Becky.

I think she needs the same punishment as the last girl we caught doing this, I said as I lead Beck over to the table and bent her over it. Chris agreed as he stepped up behind her. I lifted her skirt and lowered her panties as Chris took one of her butt cheeks in hand and gave it a squeeze.

I pulled Becky's head back as Chris spanked her arse. Becky gave out 10 yelps as Chris slapped her cheeks. I pulled her up and spun her around until she was knelling in front of Chris. With a quick flourish I has his trousers open and on the floor with his pants.

I pushed Becky's head onto Chris's cock and told her if she wanted to be a slut, she would be treated as one. Chris began to skull fuck her as I held her in place.

I took my hands off of her head and she stayed in place, and actually started to bob in time with Chris's thrusts. I dropped to my knees and lifted her skirt exposing her red arse. I slipped my head between her legs and stuck my tongue into her hole and spit saliva into it as I tongue fucked her. Soon my tongue as joined by a couple of fingers and I knew she was ready.

I stood up and pulled her off Chris's cock. I knelt on the bed and lift my skirt exposing my arse. Becky did not need me to tell her what to do, she stood and walked over to me, bent over and pulled my panties to the side and started to eat me out. Chris then started to eat Becky out.

After what felt like hours, I invited Becky onto the bed with me, and we presented our arses to Chris. He did not need any encouragement as he lined up behind Becky, with a push he was balls deep in her. I grabbed her by the tie and pulled her mouth to mine, as we shared a French kiss as Chris fucked her.

I wanted Chris to last for a long time and the earlier blow job I gave him was certainly helping. I told him to pull out of her and get in me, he did as he was told and eased into me and started to fuck me. All this time Becky and I made out, and this was certainly turning on Chris even more.

Chris alternated between fucking me and Becky and we both came at least once; I could see Chris was struggling as we kept bringing him to the bring the brink, then stopping him. As he pounded Becky, I climbed between his legs and sucked on his balls. I felt them twitch as he unloaded into Becky. He collapsed on top of her, cock still deep within her.

Finally, Chris recovered enough that he rolled off Becky with a plop as his cock pull free of her boy pussy. I then made the introduction of Chris to Becky and explained that they could save themselves out and save a lot of money if they helped each other. Chris had no idea about Roger's alter ego but was pleased to meet her and would love to have her over to his apartment. Becky accepted, and thanked me for the introduction.

We sat on the sofa and had a drink. Becky loosened her tie and opened her top button, she has they just been well fucked look on her face.

As we chatted I explained that I was leaving for university in a few weeks and I was not planning of carrying on my little service. I also had grown fond of Chris and Becky and thought they could help each other out.

I popped to the toilet and when I came out Chris and Becky were kissing as she stroked his cock back to life. When he was hard again, she swung over his lap and lowered herself onto his cock and started to ride him. The sight made me hard so I sat in a chair and slowly stroked myself through my skirt.

Becky was not taking it slow this time and Chris shot his second load into her and she shot her load into her skirt. As she came down, she climbed off Chris, and crawled over to me. She stuck her head under my skirt and took my sissy clit into her mouth. I lasted about ten seconds as I unloaded into her.

Chris gave us both a kiss and made his goodbyes. Becky and I changed into out night things and slipped into bed. I was quickly asleep.

I woke late the next morning, my head throbbed since I was not used to drinking. Roger dressed in jeans and blue shirt handed me a coffee, and I gratefully accepted it.

He told me that Becky would be visiting Chris later in the week. He asked me if I could help him get an identical uniform to mine. I told him to keep it, if I needed a new one, I would buy another.

I took a long shower and dressed in a floral summer dress. I skipped breakfast and as we checked out, we saw Chris and Sylvia. I was shocked when Sylvia leaned into me and whispered in my ear that she was thankful to me for helping Chris out with his little quirk for sissy boys; and also, for being a standing bridesmaid.

On the drive back I had Roger stop off at a petrol station, I told him I fancied a day out with Becky. He at first was reluctant but soon he was strolling across the forecourt to the car in a pair of 3-inch shoes.

We drove to the coast and had a fabulous time walking on the beach, eating fish and chips. Just a couple of girlfriends on a day out, we even had some guys hit on us, but after the last night we just were not in the mood.

Becky was going to change back to Roger before we left, but I assured her she could change back at my place. As we drove home, I felt like Becky was a kindred spirit and a life long friendship was formed. We are still friends to this day.

Becky was a little shocked at my housing situation when we reached my squat. I told her I was OK with it but she insisted I stayed with her until I moved one, rent free. I told her I would still be working as sissy prostitute until I left. She said that she understood, and I still had an offer of a roof over my head.

An hour later Roger loaded the last of my few belongings into his car and drove us to his apartment block.