tagTranssexuals & CrossdressersWorking for a Living Ch. 06

Working for a Living Ch. 06

bycall_me_dana©

I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jaime! You are beautiful!" We had lost track after high school but I found Rachel about four years ago and we'd talked off and on since then. I had sent her a few pictures of me after I told her about my change in life. "Your pictures are not nearly as pretty as you are standing right here!" Her comments almost made me cry and we hugged tightly as old friends do.

I grabbed my bag out of the back of my pick-up and she showed me inside the place. The entryway alone is larger than my apartment back in Idaho. We spent the next 30 minutes walking around the house and showing me to my room. "A couple days, if that's alright," I replied when Rachel asked me how long I'd stay.

"Stay as long as you'd like - you can see we have plenty of room! Besides, Peter won't be home until late tomorrow and I'm dying for you two to meet."

Just then, a dark-skinned young woman entered with two iced teas on a tray. She smiled as Rachel introduced me to Maria. The iced tea tasted quite refreshing after the hot drive through the desert but I could already feel the Pacific Ocean breezes. "We should take this outside but would you like to shower or freshen up first?"

"A quick shower would be great. That desert heat with no a/c is killer on my skin."

"Take your time. I'll be out by the pool - where your suit. Just follow the cool breeze and you'll find me."

Rachel left and closed the door behind her. I unpacked a few things and found my shampoo. The shower was immense with a window looking towards the beach. I stripped off my clothes and let the cool water run over my body. I innocently touched my breasts as I think back to Senior year and my time with Rachel. She was the first girl - the first anyone actually - that I had ever been with in life. I could feel my cock become a bit aroused and so I shook those thoughts from my head. I have a bathing suit to wear.

I find her by the pool as I follow the coastal breezes and walk outside. Rachel is sitting on a chaise overlooking the Pacific Ocean. I smile at her golden-brown body as she sits in a light blue, wicked weasel suit. Mine is a bit less revealing but my 36C breasts swell against it nonetheless. No sooner do I sit down then Maria appears and asks if I'd like something to eat or drink. "She makes wonderful margaritas," Rachel offers. And in just a few moments a pitcher of margaritas is delivered to us with a bowl of chips and dip.

Rachel's right and the first margarita goes down quickly. By the second pitcher, I find myself glancing at her body more and more often. The suit she wears really only covers her nipples and lips and when she walks into the pool, her entire ass is on display for me. I'd like to think the suit is for me, but the absence of any visible tan lines tells me it's her standard. Or perhaps, she usually suns in the nude and the suit is for me in a way. Of course, I'm also aware of Rachel spying glances of my body as well. My breasts are new to her so I'm sure she's curious. And I know she's trying to figure out how I stayed tucked in the bikini I'm wearing.

As the sun sinks into the Pacific Ocean, Maria brings us both covers to wear. We eat dinner on the porch and drink more of Maria's fantastic margaritas. The evening is spent talking through parts of life - both old and new. After dinner, Rachel tells Maria she is finished for the evening and she is free to go home. Apparently they have a room for her on the nights they entertain, but most evenings she goes home to her own apartment.

We're now sitting side-by-side on a cushy outdoor couch. As the heat of the evening grew, I no longer felt compelled to tuck. We both know so why try to hide. Rachel turns to me and slurs through the tequila just a bit, "Are you going to show them to me or not?" She smiles and laughs as she asks.

I smile at Rachel. I too am feeling quite relaxed from the tequila and honestly, I've been waiting all afternoon for her to ask me. I sit forward on the couch so I can face her as best I can with us both on the couch. I reach around and untie my bikini top and let it fall to my lap. My breasts really are quite amazing - I've been told many times. 36C is the perfect size for my body and they hang perfectly on my chest. My nipples are already hard and full. Rachel's eyes light up as she seems them. Without a pause, her right hand reaches up and caresses first the left then the right one. I feel my body shiver at her touch. "They are amazing Jaime. I love them!"

I reach out with both hands and free her nipples from the nearly non-existent suit. I remember her nipples being very sensitive and my thumbs rub over them. Rachel was also small and LA living surprisingly hasn't changed her 34B's but they feel wonderful under my fingers. I pause, looking into her eyes for confirmation, before bending down and taking her left nipple in my mouth. My tongue flicks across her nub as my lips suction tightly around it. I hear her audibly gasping with my attentions.

The Summer evening is just a bit chilly with a breeze blowing off the Pacific. Rachel suggests we should continue this inside and leads me by the hand upstairs to her massive bedroom. Maria, as is her duty before leaving, has turned down the bedcovers for Rachel. We fall onto the bed sheets in just our bikini bottoms. Rachel pins me on my back as she climbs on top of me. Her mouth presses to mine and we kiss for the first time in nearly 10 years. Her mouth is warm and inviting and I delight in the sensation. The feeling of her breasts pressing to mine has my cock hardening. With her lying on top of me, she feels it too.

"We rarely had a bed for this in high school," Rachel says as she slides down my body. Her mouth covers my breasts, sucking and biting and kissing as she does. She is fantastic at this and it occurs to me that I am not her first woman. By the time Rachel kisses her way down my tight belly and tongues my navel, my cock is pressing against the top of my bikini. I've put a pillow under my head so I can watch this beautiful creature make love to my body. The moment arrives and she slips her fingers inside the waistband. I lift my hips slightly and she pulls my bikini bottoms over my hips. I see the big smile on her face as she sees my erection. My small patch of pubes were matted and wet from my precum.

I watched as Rachel's extended tongue licked at my juices but did her best to avoid my cock. She got between my thighs and took the left, then the right, ball into her mouth. She sucked and licked it like the biggest jawbreaker she'd ever had. My right ball fell from her lips and suddenly she was taking the crown of my cock into her mouth. I felt like a teen again as memories of the first time in my dad's truck flooded back into my brain. Only now, Rachel had skills for this. She slowly took my cock into her mouth. Her tongue coated and licked my skin as she took me deeper. I watched her head ride up and down on my seven-inch cock. She had me nearing an orgasm when she let it slip from her lips. My disappointment was audible.

Rachel kissed her way up my body and then kissed me on the lips. "I want the first one to be inside of me, not in my mouth." I smiled and rolled over on top of her. I repeated what she had done to me and found my way down to her sex. The bikini was quickly removed and I covered her smooth pussy with my mouth. I could already taste her juices and just wanted her nice and wet and wanting for me. "Please get inside me Jaime."

I moved over her body and looked her in the eyes as I pressed my cock to her waiting pussy. She brought her thighs up around my hips and pulled me into her. My thick cock slid easily into her wet pussy. "I don't remember you being this big!" i grinned and pressed my lips to hers. Rachel's hips moved up to meet my downward thrusts. The margarita's had us horny but relaxed with one another. We fucked together, changing speeds from slow to quick and back to slow. Both of us enjoying the moment and the memories of youth.

Finally I could feel Rachel beginning to tense underneath me so I picked up the tempo. She pulled me tightly to her when her orgasm rocked her body. I could feel her shaking and kissed her hard on the mouth. I relaxed and my cock erupted cum inside of her tight pussy. We fucked three or four more strokes with my cock feeling alive inside her before I collapsed on top of her, both us panting and sweating.

Finally I rolled off of her and we lay side-by-side. "I guess you were my first - twice!" We both laughed at that sound of her declaration. Fucking behind us and alcohol-fueled, we talked more openly about my lifestyle and hers. They both were interesting and not what either of us would have imagined at the Senior Prom. I think I fell asleep first, but I'm not really sure.

#

Their was a light a knock on the bedroom door but neither of us heard it. It was only eight in the morning. "Rachel, it's time to wake up," Maria announced as she walked into the room. I lifted my head first to see her. I am lying on my back with my slightly sunburned breasts uncovered. Maria smiling at me, "Excuse me Rachel. You did want me to wake you for your appointments." Rachel is on her belly and acknowledges Maria. I note that Maria takes one more look at my breasts before leaving the room.

The day was a blur of shopping for the two of us in Rachel's Cabriolet. Even in a place such as Malibu, two well-dressed women, one blonde and one brunette, in a convertible Porsche rates quite a few looks from those on the street. We found time for some lunch overlooking the ocean in between all the shopping. Late afternoon finds us back at the pool and drinking Maria's margaritas. Peter is due home in time for dinner. Lying on my stomach, I feel Rachel's hands on my lower back. She is tracing the outlines of my tattoo. It's a brightly-colored floral print spread across ten inches of my skin - nearly hip to hip. I had it created shortly before my implants as a sign of my impending womanhood.

"It's really beautiful work," Rachel commented. She had to push down the top of my bikini bottom to see the entire piece.

"Thanks. I mostly designed it myself. A friend told me about this pro in Vegas so I had her ink it for me." My penis wiggled underneath me as I felt her fingers at the top of my crack.

"I really enjoyed last night Jamie. I do hope you'll let Peter join us this evening."

I turned my head to face her. "Really? He would like to join us?" From our post-fuck chat last night, I should not have been surprised but I was.

"I told him about you when you called about a visit. He knows you were my first a long time ago and he knows about last night. I think he would have been disappointed if we hadn't last night."

I had to shift my body slightly as I could feel my penis growing as I listened to Rachel. I have seen a few pictures of him around the house and he looks gorgeous! I could feel myself blushing at the thoughts.

Maria called out from the house, "Peter's plane has landed. He says he'll be home in about an hour. I'll plan dinner for 7, if that is good with you?"

"That will be great. Would you bring us another pitcher?"

I started laughing, "Great. You'll have me drunk by the time he gets home!"

#

Meeting Peter was amazing. He brought home roses for both of us. We had put on slightly more clothes for dinner though Rachel had asked me not to wear a bra and leave my blouse mostly unbuttoned. My shorts were snug and greatly accentuated my ass. Rachel was wearing a skirt and blouse. We were definitely dressed as eye-candy for Peter.

After Maria left for the evening, Peter began asking me a few more personal questions. Feeling comfortable with him - and several margaritas - had my answers flowing easily. "I know Rachel has told you we both enjoy life and the pleasures that present itself to us." He leaned over and gave me a kiss on the cheek. When I didn't move, his lips moved to my lips. I returned his kiss. When our lips broke free, Rachel was standing beside me. She bent down and pressed her lips to mine. The sensation of both of them had my head beginning to spin in a good way.

The evening is much warmer than last night with just a hint of a breeze. "I would love to see you nude, Jaime. Would you indulge me this request?" I looked towards Rachel and she smiled that it was OK with her. I stood on shaky legs and walked a few steps away from the table. I was in clear view of both of them as Rachel moved to Peter's lap. Unbuttoning the last two buttons on my blouse, my breasts were exposed. i slipped the blouse off my shoulders and let it fall to the patio floor. Peter's hand was under Rachel's skirt and I knew he was stroking her clit. Turning away from them, I look over my shoulder and smile. I see Peter admiring my tattoo. I wiggle my ass as I unzip my shorts and begin to let them slide over my hips. When they are below bare ass cheeks, I turn back around to face them. The tip of my cock is visible as I slide them down my thighs. Peter smiles as he sees me nude for the first time. Rachel is already grinding on his cock as he fingers her sex. My cock is nearly fully erect. With one hand, I play with my tits. With the other hand, I gently stroke my cock for them - and me.

"Beautiful! You are a beautiful, sexy woman Jaime!" I walk to them as he speaks to me. Reaching down, I pick up my margarita and drink what is left in the glass. His left hand reaches out and begins to stroke my cock. "Rachel tells me you are quite ... skilled."

Smiling, "I too enjoy the pleasures that present though I don't think I have as many opportunities as the two of you. And I take pride in my ability to enjoy those pleasures." I bend down and kiss Peter. With her still on his lap, my right breast swings in front of Rachel and she sucks my nipple into her mouth.

A few minutes later have the three of us nude under the stars in the backyard. A large padded area is tucked beside the pool. Rachel has sucked both Peter and I while the two of kissed and he played with my tits. I love running my hands over his body. Rachel had told me he works out daily and I can feel the muscles on his body. I already can feel myself wondering what it will be like to be fucked by this incredibly handsome man. "I understand you enjoyed her pussy last night - would you like to enjoy her ass tonight?," Peter asks me and then adds, "We could share her." Rachel has a firm, tight ass that is golden brown and I'm guessing she will be a very tight fit for my cock.

"I would love to have your ass," as I pull Rachel to her feet and press my lips to hers. I move onto the padded area and lie down. Rachel climbs on top of me followed by Peter. Rachel spits into her hand and rubs it against the rim of her asshole. I'm sure her pussy is well lubricated after sucking both of us. Reaching around, Rachel guides my cock to her asshole as she faces away from me. I feel my crown pop inside her hole and she lets out a little 'yip' as it does. Rachel is soon sliding down my cock as it fills her tight, as expected, asshole. Rachel leans back onto me and Peter moves between her thighs. His cock is slightly longer than mine but not quite as thick. He has a very thick mat of dark pubes. He presses his cock into her pussy and penetrates her deeply with his first thrust. It's been quite sometime since I've had a similar situation so it takes me a couple moments to get into the rhythm of fucking.

As he fucks Rachel, Peter takes turns kissing her then kissing me. Our bodies move together as one after some time. Sooner than I would have expected, Peter smiles and I know he is filling her cunt with him cum. He pulls out and climbs off the padding. "He wants you to really fuck my ass. He gets a rush from watching!" Rachel tells me over her shoulder.

"Then you need to be on the bottom." We carefully flip over with Rachel now on her hands and knees. My cock nearly slips from her sexy ass but I won't let it. I'm now practically standing over her with my feet outside her knees and my cock thrusting straight downward into her asshole. Peter returns with wine and three glasses.

"I see things have gotten interesting since I left you two alone." I'm now riding her asshole with long, deep thrusts. I know his cum and running down her inner thighs and thought of it excites me more. The power I'm feeling is intoxicating as my cock slides in and nearly out of her tight hole.

"Fuck me Jaime, Fuck my ass!" Rachel cries out as my cock pounds her. I can't hold out any longer and I bury my cock deep inside her. I shoot a thick stream of cum into asshole and collapse on top of her. Rachel is murmuring about her asshole being on fire from my cock.

"That was amazing Jaime," as Peter drinks from his wine goblet. His cock is nearly erect from watching us. "Do you like being fucked as much as you obviously enjoy fucking?" A wicked grin crossing his face as he pours two goblets of wine.

I roll off of Rachel's body and take a goblet from him. Gulping it, as if it were air, I set the glass down. My body is on fire with lust and I want to be fucked now. My cock is semi-erect and lays against my cum-soaked pubes. Rachel moves slowly to drink from the third goblet with cum dripping from her pussy and asshole.

Grinning back at him, "Even more!" I lift legs up so my knees are against my tits. Wrapping my arms around my thighs, I reach down and spread my firm ass cheeks to expose my hole to him. "Would one of you two sexy creatures be kind enough to tongue me first?" My body is totally exposed to Peter and his sexy cock. To my surprise, it's Peter's tongue that licks my rim. He buries his face against my backside and I can feel his tongue tracing circles. My breathing comes back to me and I do my best to relax my muscles. Warm spittle hits my rim and I feel his tongue pushing it around until he senses I am ready for him.

Peter pulls me to the edge of the padding and presses his cock against my hole. He smiles as he shoves it inside of me. A man like Peter can see when a girl wants to feel it. He thrusts again and goes deeper inside of me. I yell out but it's from the feel of his hard cock exciting my body and mind! Peter leans into me as he buries his cock to the hilt. I feel his balls slapping my ass cheeks as I hang over the edge. Rachel reaches out and strokes my cock between my thighs. Peter's weight has me nearly immobile as I'm pinned against the padding. I feel his cock inside me and it feels so great. He continues to thrust, varying his tempo to prolong this for both of us. I realize he came quickly inside Rachel so he could watch us really fuck.

I'm enjoying looking up through my ankles and seeing this sexy man plow my hole. I've lost track of the time but he fucks me for more than twenty minutes before he tells me he's going to cum inside of me. I smile at his words and feel Peter bury his cock inside me and his hot cum shooting. Another thrust and another stream of cum fills my bowels. My hole feels like a train-wreck from over twenty minutes of pounding. My cock is throbbing and Rachel jerks it in her hand. We all watch as a thick rope splashes on my tits.

#

I awake the next morning with the sunshine streaming through a window. I look around and realize I'm the only one still in Peter and Rachel's bed. Dragging my body out of bed, I feel like I can barely walk. My ass is sore from Peter taking me twice during the night. Finding a robe, I put it on and go downstairs to find Rachel. She is sitting outside in a similar robe with a steaming cup of coffee and the remnants of breakfast. "Hey sleepy-head! I thought you'd never join me!" I smile and gently sit down at the table.

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bycall_me_dana© 4 comments/ 17643 views/ 3 favorites

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