Join the best erotica focused adult social network now
Login

Girly Obsessions

"Based on a real adventure with embellishments of wishes"

27
17 Comments 17
14.7k Views 14.7k
7.2k words 7.2k words

All of my life from the time I was young to now at twenty-five, I have had an obsession with women. It is not that I like them (which I most certainly do) but more that I want to be like them, act like them, and most importantly dress like them.

It started when I was very young and developed an interest in the legs and nylons of women which I found fascinating. The sheer and soft material was incredible to look at and to touch. I was entranced with the way girls' legs would look with them on and often was frustrated by not being able to wear them openly like most girls did.

I would often "borrow" my mother's nylons and wear them on my young slender smooth legs, pretending I was a girl and crossing my legs like a girl. This progressed to shoes, heels to be exact which I started wearing along with the hose. I would prance around the house (when no one was around of course) and marvel at how pretty my legs looked in high heels and hose. I was fascinated at why nylons and high heels were only worn by women and they wore them only to attract guys.

Next came the dresses, which really completed my obsession (at least at a younger age). Pretty skirts, mini-dresses, flirty dresses, little black dresses, off-white girly dresses (my favorite), were all worn by me. It was wonderful and I felt like a real girly girl when dressed this way.

Sometimes I wish I could explain this obession to someone and be cured of it, maybe it is like an addiction. I often sit at the computer and just look for girls clothes online. I peruse all the shoe sites, especially ebay which has load of cute heels at great prices. I love to go shopping and look for pretty dresses, nylons, stocking, tights, panties, and especially shoes....high heeled sandals are my absolute favorite. I walk in to the stores (dressed like a guy) and have no problem looking at all the girls clothes.

I have such an attraction to girls clothes that it dominates my thinking. I often feel it is totally unfair that the beautiful girls I see get to look and dress like they do...and I don't like them for that reason, but at the same time I am in awe of their femininity and their clothes.

I am in awe of how pretty girls can be when dressed in beautiful clothes. Sometimes when I see a poorly dressed girl or one that is dressed grunge, I want to scream at them and tell them to go get pretty...you are a girl and should look like one. Mostly I get jealous of how lucky girls are, to able to dress the way they do, sheer, silky, cute, flirty, girly, pretty, tight, sexy, which are all meant to attract guys and certainly do.

After college I had gone to work doing consulting jobs for a couple of years and got some great experience working one-on-one with clients. I had decided to try and go at it on my own with a couple of my key accounts, and it had worked out well. I would spend a week or two at different client sites helping them with their computer systems and had all the work I could handle and was getting paid quite well.

Now that I was on my own I had stepped up my dressing habits with a nice collection of heels, dresses, lingerie, skirts, hosiery, makeup, etc. I kept my hair long and pulled back; and had maintained a very lean weight at 140 lbs and I stood 5'-7" tall. I still never ventured out while dressed but was getting a bit bolder as time went on.

I had just completed work with one client and was to see a new potential client in the same city. I have been traveling here numerous times before and during an off day decided to get my first manicure and pedicure. I really enjoyed the pampering and loved how nice my nails looked when covered with a shiny clear top coat. They made my toes look really cute when I got back to my room and slipped into some strappy high heeled sandals (I always traveled with an extra suitcase filled with my girly things).

I went out immediately and bought some pretty pink nail polish as well as some polish remover and sat down to paint my toes just like a girl. It was wonderful and I felt very feminine doing so. I messed up a lot but after two or three tries I got a pretty good result. My feet looked very pretty with the polish and they looked even better with the sandals on. I was totally hooked on this and went out to get additional colors (reds, hot pinks, bronze, light pink). I was really excited to get my next mani/pedi and decided I would ask for some color next time.

Before the next trip to the nail salon, I put on some very light pink polish on my toes. It had a very subtle shimmer and the nail girl would surely know that I had more than clear polish on my toes. I was extremely nervous but also very excited by the prospect that someone would be seeing my feet with real polish on them. She proceeded to give me my pedicure and started out by removing the polish that was on my toes, she definitely knew.

When she finished with the pedicure she put on a clear coat and asked if I wanted to pick out a color, oh this was heaven. The owner of the salon noticed this and came over to suggest some colors, it was so much fun. She picked a really nice pinky purple color that look really cute and the girl started to paint my toes in front of everyone in the salon. I was really embarrassed, but kept on reading my book and tried to not die of freight.

Once complete she asked if I wanted my finger nails done as well, but I declined (from sheer terror). My toes dried while I got the manicure done with a clear polish. I was wearing flat open toes slides (men's) that showed my toes clearly and walked right out of the salon feeling really girly but also very nervous about people noticing.

The next trip to the salon I would go all the way, manicure and pedicure with full polish on both hands and feet. While I have smallish hands they don't look too feminine especially with short nails, so I began to grow them longer in anticipation of my salon visit. By the time my trip began they were nice and long extending about a half inch beyond my finger tips. Because they were so long I developed the very feminine habit of looking and worrying about my nails. I was constantly cleaning the underside of them and would file them to a nice shape.

I was very excited for my next visit to the salon with my nails looking much more girly than ever before. I walked in and said hello to the girls (who now knew me and my little fetish) and was brought over to the station to begin. The girl doing my nails was Ally; she was very nice (and pretty) and treated me just like a girl while she began work. She cleaned my toe nails, shaped them nicely and made my feet really soft and smooth.

We chit chatted a bit and she helped me pick out a nice pearly color polish and began to put it on my toes. After a bit of silence she said, "Can I ask you a question?" I nervously agreed.

"Why do you come in here and get your nails painted?"

I confessed, "Well, it is hard to explain, but I really enjoy the whole process of getting them done.....I love how it looks when they are painted...aaannnnddd I am kind of obsessed with girly things."

Wow I never told anybody this stuff before. She looked at me kind of sweetly. "And what do you do after you have your nail painted?"

"Well, I usually go back to my hotel room, open a bottle of white wine, and get dressed up."

"Dressed up??? In what?" she asked.

"I have some pretty girls clothes....dresses, heels, nylons."

"What happens after you look all girly?" she mocked but in a cute way.

"I drink my wine, look at myself in the mirror and act like a girl....and then I uuuhhhh...pleasure myself," I responded very quietly.

She smiled, "I know lots of girls that do that all the time and it sounds like a fun way to spend an evening, like a girl's night."

Then to my complete shock she asked, "Would you like to have a girl's night with me tonight?"

I turned bright red but got very excited and stammered out, "Uuummmm ok, but you have to promise not to laugh at me to much."

Ally looked into my eyes sexily and said, "I don't think we will be laughing too much," as she winked.

"What will you be wearing tonight?"

"I have a pretty off-white dress, with some strappy high heel sandals."

"That sounds very cute, I will be sure to dress appropriately for you."

I was trembling at the anticipation of tonight and was getting very aroused. Ally noticed and smiled at my eagerness. She completed my toes, which looked great, and then started on my hands. "Your finger nails are nice and long....they will look really pretty with the polish on."

"Thanks....I have been growing them out for the last 3 weeks, hoping they would look good with my manicure." She spent a long time on the manicure making sure my nails and cuticles were perfect. She then coated them with a clear polish, then two coats of the pearly polish.

My hands looked beautiful and I thanked Ally for the wonderful job. She smiled and gave me a kiss on the cheek whispering, "See you tonight...girlfriend."

With my manicure and pedicure completed in a nice pearly white color that matched my beautiful dress and heels I raced back to the hotel to get ready for Ally who was arriving in an a couple of hours. I chilled two bottles of white wine and started to get ready. A took a nice hot bath and shaved my legs and other "hairy areas" very closely.

I made sure to clean out my backside well using an enema wash several times. Once clean and smooth inside and out, I put on a nice body lotion all over. I slipped into a thong panty and slid my girly legs into off-white stay up stocking.

They were very sheer and I could see my beautifully painted toes thru them clearly. I then slipped into my dress which was an off-white cocktail dress that cupped my "breasts", hugged my hips and fell to a flirty hem that ended six inches above my knees.

I then put on my favorite heeled sandals. They were off-white strappy shoes with thin straps around the ankles and a pretty ornate wider strap that went up the instep to the ankle strap, easily the sexiest shoes I have ever worn (or seen).

I then did my hair, which was long for a guy, styling it in a feminine manner. Finally I put on some make-up, foundation, eye shadow, liner, blush and lip stick and felt I looked as girly as I could. I felt very pretty, very girly and very excited for Ally to arrive.

I poured myself a glass of wine and quickly drank most of the glass to calm my nerves a bit. I heard a knock at the door and looked thru the peep hole to see Ally smiling.

I took a very deep breath and slowly opened the door and let Ally inside the room. She looked really cute and as promised dressed appropriately. She wore a beautiful spaghetti strap red dress that flared out at the waist and had a very flirty hem that was well above the knees. She had on very sheer off-white hose that blended into her skin and was wearing some very sexy black sandal heels which had really thin straps that also wrapped around her ankles.

Her nails were perfect and matched her dress color very well, I could see her toes thru her hose also and they looked good enough to eat. She walked in with a big smile and we kissed on the cheek, "Wow you look fabulous," she told me,

"I cannot believe what a girly body you have especially those legs, they are precious."

I blushed and smiled replying, "Thank you so much for saying that it makes me feel really good inside......and I am totally jealous of how pretty you are and how great you look in that dress and those shoes....I must get a pair of those shoes before I leave."

We sat down on the couch and I poured us both some white wine. We sat and talked like girl friends do, touching each other and commenting on our outfits. "We picked the right color for your nails, they look perfect for the dress," Ally commented, "and your shoes are very sexy."

"Thanks, I hoped the color was right and it turns out it was."

After another glass of wine we settled down a bit. "Ally," I asked, "what do you think about my girly activities?"

"Well...you are different than most guys, but I think exploring your feminine side makes you a better partner to a girl and I think that is very appealing, girls are also generally more open to other girls sexually and you make for an interesting dynamic because you offer both sides in one pretty package."

Wow was I hot after that statement; I looked into her eyes and kissed her softly on the lips. She returned the kiss and our lipstick painted lips mixed together and our tongues intertwined. We touched and kissed each other for a long while savoring the moments and allowing us to caress each other softly.

Ally lay back on the couch and I slide my hands along the hose of her perfect legs, parting them slowly and revealing her pretty panties. I moved them to one side and began my first "lesbian" experience.

Ally bucked, squirmed, and moaned as I used my tongue and lips to treat her pussy to several orgasms. I had done this before to several girls, but doing this while looking and feeling like a girl was a huge turn on for me. She then asked me to lie back as she would return the favor. Expecting a blow job I was pleasantly surprised as Ally began by removing my panties and spreading my legs wide apart.

Lifting my balls to one side she began licking my hole like a pussy. I began moaning at the wonderful feel of this new experience and truly felt more feminine because of it. She then inserted her middle finger into me and continued the tongue treatment. I was in heaven and felt wonderfully filled as she inserted another finger deep into me. Then Ally's third finger entered me and I felt myself begin to orgasm but not like normal.

It was deep in my body and slowly made its way from my painted toes to the top of my head. Ally sensed my moment and pressed her fingers deep into my hole. She also took my very hard cock into her mouth for the first time, going down all the way to the base. I screamed out, "OOOHHH, I am going to cccuuummm." Ally pulled back off of my cock a bit as I let go of the best orgasm I have ever experienced.

Ally's fingers continued moving inside me as I let out stream after stream of hot cum into Ally's mouth. After the last of my eruptions Ally came up and kissed me deeply, allowing my cream to slip into my mouth with her tongue. I was feeling so feminine that I did not even react and hungrily accepted my cum, swallowing it down eagerly. We continued kissing and cuddling as our initial passions calmed a bit.

We poured ourselves some more wine, smoked a cigarette together and felt very relaxed. Ally played with my hair and was telling me how pretty I looked. This was definitely the best experience I have ever had.

Ally then suggested we touch up our makeup and pulled out her bag of cosmetics. She fixed me up nicely and gave me some good tips on how to make myself look better. I sat and watched her as she fixed herself and sighed at how lucky she was to be able to do this all the time and go out in public looking as pretty as she did.

"Have you ever gone outside while dressed?" asked Ally.

"Not where anyone could see me, but I have been a bit daring like when I paint my nails at a salon and walk back to the hotel......I also usually put on a very light pink polish on my fingers and toes regularly."

"Have you ever been with guy?"

"Nooooo.....but it has crossed my mind." "

"What crossed your mind......sucking a nice big cock and making a man cum or being treated like a real women and taking a man deep and feeling him cum inside you?"

"Both....but I would be way to scared to go through with something like that since I don't think I can pass as a girl."

"Oh yes you can girl!!!" screamed Ally.

"And I would like to prove it to you right now!"

"NO WAY! Everyone would certainly know I was really a guy."

"How about we go down to the bar and sit in a nice quite corner and I will call a friend of mine to join us....we won't tell him anything unless he can tell."

"I will only agree if you redo my makeup and hair AAANNNDDD I am convinced by looking in the mirror."

"OK.....let's get to work making you look like a total girly girl."

She called her friend who agreed to meet us at the hotel bar in an hour. Then she began to redo my face. She used more makeup than I usually used convincing me that I need an evening look and a bit more foundation. She spent a lot of time on my eyes and lips and I was thoroughly enjoying the makeover.

Next she got some hair extensions out and incorporated them into my hair making it much longer and fuller. After putting on some shiny lip gloss she said I was done and I stood and walked over to the mirror. I was a bit shocked at the new me....I was really pretty and looked very feminine.

I softly touched my face and hair to make sure it was me underneath, then I turned to Ally and hugged her and thanked her for making me look so good.

She smiled and said, "I told you so," in a cute mocking manner, "now let's go meet your man."

I had some confidence in my look after seeing myself in the mirror, but I was still extremely nervous as we waited for the elevator. As the doors opened we walked into the elevator with clicking heels and noticed two handsome business men heading down stairs. They looked us over wantingly and one guy said, "I want to go wherever you two are going".

This made us both smile and Ally quickly responded, "That maybe arranged for another night, but tonight we are meeting a friend for a drink."

"Too bad, but we will be looking for you two tomorrow!" said one of the guys as we walked out of the elevator toward the bar area.

I was feely very good after that exchange because of the confidence boost of being "hit on" on my first time out. It also felt really great to be out and about, hearing the click of my heels, feeling the bounce of my skirt, and the swish of my nylons rubbing together. It was invigorating seeing people notice you, glance at your legs, and turning heads because of how pretty you look. As we walked into the hotel bar a waiter quickly sat us at our chosen table and commented on how beautiful we looked. We ordered champagne and sat back on the cushy chairs, crossing our legs and chatted a bit. "I told you.....you're passing not only for a girl, but a hot girl.....did you notice those guys on the elevator, there jaws dropped when we walked in."

"I have to admit you were right.....I am just loving this and I feel so right with everything."

The champagne arrived and we toasted and sipped. I noticed the lipstick mark left on the glass and smiled to myself that I had made that mark. We drank and talked a bit more when a handsome looking guy approached us and sat down between Ally and me. Ally reached over and hugged and kissed Steve, and introduced me to him. "Steve this is my friend Jaime who is in town for a few nights on business."

AndiBlake
Online Now!
Lush Cams
AndiBlake

"Hi Jaime, very nice to meet you," said Steve as he hugged and kissed me on the cheek. "You girls look really nice tonight, what is the occasion?"

Ally said, "Well we were having a girls night, painting our fingers and toes, then we did makeovers, and we felt we were all made up and no where to go......so we dressed up and decided to go."

"Well thanks for calling me, I have never been to a girl's night before but I am willing to come along."

Steve ordered a wine and some more champagne for us. We talked, drank and were have a nice time....I almost forgot about how I was dressed, but would notice again quickly as I touched my skirt or re-crossed my legs. I was also noticing the looks and smiles from the few other guys in the bar; it was very comforting to me and confirmed my confidence.

I looked over at Ally and she winked at me giving me a sly look and nodding her head towards Steve. I smiled as my stomach fluttered; Ally was going to ask Steve up to the room and was asking if it was ok with me. I nodded to her in agreement and instantly felt terrified. She whispered into Steve's ear and he glanced over at me smiling broadly. I returned the smile as we stood up to go to the elevator.

As we rode up we both nuzzled up to Steve and could sense and see his excitement growing. Opening the door we pulled Steve over to the bed where Ally and I sat down next to each other. Ally undid his pants and lowered his silk bikini style briefs (they looked a little like panties...hhhmmmm) down his smooth legs (he shaved) releasing a nice looking very hard cock. I was really scared now;

Ally noticed and began to kiss me with an open mouth and tongue, while guiding me closer to Steve's cock. As we kissed I felt Steve's cock rubbing our cheeks and our lips. Steve was moaning and kept saying "This is so dam hot." Ally's hand grabbed the cock and she kissed its head and licked up and down the side. I was so close to it that I mimicked her actions, tasting a man for the first time. It was really warm and very smooth....and I tasted his clear pre-cum which had formed at the tip. Ally and I continued our lip battle with Steve's manhood for a few minutes and I was really starting to get into the act.

I wrapped a nylon covered leg around Steve leg, bringing him closer to me and then grabbed his cock and took him into my pretty lips. I was looking up into his eyes as it passed my lips and I saw a look of utter joy and submission in his eyes. I took him in as far as I could and then backed him out before plunging in again.

Ally was right next to me licking his balls and with her hand caressing my smooth legs. I realized how much control a girl can have over a guy by the look in his eyes....Steve would do anything for me right now as long as I continued to suck on his cock.

Ally and I switched tasks a couple of times until she whispered in my ear to finish him off myself. I had quickly learned how to perform fellatio and was taking in Steve all the way down my throat. I felt him start to pant quickly as I took him in really deep and gently sucked his head. I quicken my pace and was pumping my lips over his rod several times when I felt his cock get a little bit bigger in my mouth and new he was about to let go.

I pulled back a bit keeping his head in my mouth but out of my throat as he began his orgasm. The first load was tremendous and hit the back of my throat with a large volume of cum that shocked me a bit. The next spurts came with less force but continued to deposit a large amount of cum in my mouth.

Moaning I continue milking Steve until he finished and then let his cock slip out of my mouth with a kiss, then showed him a bit of the cum that was covering my tongue. Ally looked over and immediately kissed me as we shared the warm cream between us. As we parted our kiss I looked up at Steve and swallowed the cum down my throat.

I reached over and grabbed his cock, pulling some more cum out of the tip. Still looking up at Steve I licked the cum off the tip and cleaned the rest of him with a nice slow plunge down then back up. This was by far the most erotic thing I had ever done and it felt right the whole time I was doing it. I loved how Steve's dick had filled my mouth and it was very satisfying knowing I had made Steve cum so powerfully with my painted lips. Feeling the cum pumping into me as I was coaxing it out really completed my whole girly obsession knowing that I was performing just like a girl, looking just like a girl and receiving the reward of a mouthful of cum from a guy.

As I basked in the feminine feelings I was experiencing, I noticed Ally whispering into Steve's ear with a little grin. Steve looked at me in surprise but with a big smile on his face and said, "Wow Jaime, I would have never guessed you were a guy...you are just so beautiful and very sexy."

I was a bit shocked that he new AND that Ally told him and replied, "I'm sorry we did not tell you but we kind of had a bet going between Ally and me."

"Don't worry about it....I have enjoyed both guys and girls from time to time and I really enjoyed this especially from a hot girl, I mean guy.....was I really your first blow job?"

"Yes you were.....I hoped it was ok because I really loved it, it was so erotic."

"Jaime, it was fantastic and I am honored to be your first, but hopefully not the last."

Smiling as cute as I could I said, "I will be here for a few more days so I can guarantee that."

We opened the other bottle of wine, pour ourselves some glasses of wine and lit up some cigarettes after our initial sex session. Steve asked about how Ally and I met, my girly obsession, and what I did for a living. He was a very cute guy and I liked him immediately. As we relaxed a bit I asked Ally to help me freshen my makeup. We went into the bathroom and giggling like girlfriends do she asked, "SSSOOO, how was it for you, girl?"

"It was better than I ever imagined, I mean I felt so sexy, hot and girly with his big cock sliding between my lips."

"It was really hot watching you, I was getting turned on big time especially when we kissed after you had his cum in your mouth....girl he came a lot and you just took it all like you've been a girl your whole life."

"I think I may have been and finally let it come out tonight."

"So what do you want to do next?"

"I really want to be fucked like a girl and I want Steve to do it....let's fix our makeup and then seduce him like only girls can."

We touched up our faces and put on fresh lip-stick and went out and sat on the couch next to Steve. He had a big grin on his face (as did we) and new something good was coming up.

"So Steve how are you feeling....perky?" asked Ally.

"Not 100%," he replied, "but I am revving up fast with you to gorgeous girls here."

"Let's see if we can pick you up with a little girly girl fun." With that Ally turned toward me and began kissing me deeply and femininely. We touched and caressed each other lovingly while Steve watched in growing excitement. Ally laid me back on the bed on my back as she straddled my face with her legs and lifted the skirt of her dress up.

She then lifted my hem up as well exposing my panties with my very excited cock. In this sixty-nine position I began licking Ally pussy with desire and tasting her sweetness. It was quite a turn on to be doing this with Steve watching and I kept on looking over at him and smiling at his growing cock. Ally in turn began sucking my cock and fingering my hole which was making me feel incredibly good.

I was on the bottom with my legs spread wide giving Ally plenty of room to bury her pretty fingers into my hungry ass. After a several wonderful minutes of pleasure between Ally and me, I could see Steve was ready to participate. Ally removed herself from my face and my cock and guided Steve over to the bed. She took hold of his pretty cock and wet it thoroughly with her lips and tongue. Once it was nice and slick she guided it to my waiting ass-pussy. I was hoping this would be part of the activities, but was also very scared about loosing my girly virginity for the first time. I thought to myself that this would be a moment in my life that would change me...maybe forever...and that I might not return to the person I once was.

I had very mixed emotions rolling in my head, but could not deny my natural desire to be a girl and to be treated like one by a hot guy with a beautiful cock. Taking stock of my feelings and looking at my pretty nylon covered legs, painted toe nails, high heeled sandals, and frilly dress (that was hiked up to my waist) I knew I wanted that cock deep inside me. I lifted my legs up and Steve grabbed each ankle and placed them on his shoulders.

He ran his hands down my legs and up my thighs saying, "Jaime, you have such long, smooth and pretty legs"

I stammered out a, "Thank you.....please be gentle with me, Steve...it is my first time with a man."

"Don't worry Jaime; I will try to make this a wonderful experience for you."

As he did I felt the head of his rod penetrate me and I expanded to take him in. As he pushed in gently I relaxed my self as best I could. Ally was along side me whispering in my ear telling me how hot this was and what a sexy girl I was, and that this was turning her on. Steve continued pushing in a bit and then backing out until I felt his head push past my opening, which caused me to gasp and moan with a bit of pain and a lot of pleasure.

Steve paused here for a bit and continued rubbing his hands up and around my legs. This was very soothing and relaxing to me and helped open me up to Steve's penetration. With the head inside me, he penetrated deeper with each stroke and I felt the true sensation of being fucked like a girl. I began to squirm and moan at the thrust of Steve's cock and felt him touch bottom when his balls came in contact with the lower part of my ass. I was in ecstasy at this point and was filled with a desire to be fucked and feel him cum deep inside me.

Steve continued banging away at me and I was overcome with a pleasure deep inside me that I had not experienced before. Steve then pulled out of me with a pop and I looked at him with a shocked expression of desire.

"I want you on top of me," he said as he quickly lay on the bed. I was still on the bed and got on my knees and straddled Steve's torso and grabbed his cock to guide it into my waiting hole. Once in place I pushed down and felt the instant pleasure again of being filled completely. I found that I really liked this position as it allowed me to control the depth and rhythm of the fucking to my desire.

Ally also liked this because after watching me ride cowgirl on Steve she also straddled his face with her pussy and laid face down on his body which brought her face to face with my very stiff cock, which she quickly engulfed. With her receiving a good tongue bath from Steve, she began really going down on me with abandon and passion. I was on pleasure overload with a nice long cock slamming into me very deeply and a really hot blowjob going on simultaneously.

With one last thrust I felt Steve's cock expand inside of me and then begin to pulse with load after load of hot cum pumping deep into my bowels. The feeling was intense and I cried out in pleasure as a deep internal orgasm began to spread thru my whole body. I truly felt transformed into a real girl at that moment and noticed all of the things that made me feel that way, long painted nails, nylon stockings, pretty dress, long hair, high heels, and of course being fucked like a real girl.

Ally sensed my building climax and deep throated my cock as I hit my peak moment. I screamed in a girls tone and began to release wave after wave of cream into her waiting mouth. The orgasm was beyond incredible and seemed to last well beyond the time I finished cumming into Ally.

Ally released my cock and I felt her lips touch mine as we began to kiss in continued passion. She passed her mouthful of cum into me and we shared my cream as our tongues danced inside our locked lips. We broke our kiss and Ally swallowed her share of my load. Ally climbed off of Steve and I fell onto his chest with his cock still inside me. I kissed him deeply allowing some of my cum to flow into his mouth.

We both swallowed and I eased Steve's cock from my ass and I quickly spun around to clean the cum that was dripping on his shrinking rod. My stocking covered legs came around on either side of Steve's head and I felt him returning the favor by cleaning my well fucked ass-pussy. It was wonderful to service each other this way and end our steamy hot love session. His tongue felt wonderful and probed me as deep it would go cleaning me up very nicely.

We lay back on the bed and shared some wine and cigarettes to wind down from the intense sex session. As I drank my wine I was in deep thought about my future life and my strong desire to continue looking and acting like a girl. This evening I had fulfilled two of my deepest fantasies, giving a really good blowjob with a cum swallow to a guy and being fucked in the ass like a real girl. This coupled with the incredible lesbian like sex with Ally had me in a quandary.

Should I be a girl full time? Could I with my current job? I felt so right now both internally and externally, and did not see a good reason to change back to a guy. I loved the feeling I felt when I went out dressed in a beautiful dress with heels and hose; and reasoned that I had to be able to do this full time.

I decided to do a trial for at least three months to see if really wanted to change for good. I had a new potential client I was to meet with the in two days that would be a long term project if obtained and I decide to go there as a girl since I had never met with them before. I needed to see if Ally would help me, I was really excited about this.

Ally and I got up, cleaned ourselves up and put on some fresh makeup. We said our goodbyes to Steve and as he left we noticed the two guys from the elevator earlier this evening coming back to their rooms. I smiled at them and asked how their evening was. The cuter one responded, "Not too bad but it looks much better right now."

I looked over at Ally who winked at me, "Would you like a nightcap, we have some wine in our room?" They practically ran over to our room. I poured some wine and we drank and talked for a few minutes.

Chris and Neil were both very nice and cute but I sensed also a lot horny. I decided to give them a little show with Ally and then give them some nice oral sex.

"OK boys, it seems like you two are a bit, shall we say horny and we would like to help. Please stand in front of us and watch, we will let you know when we need your participation."

With that I turned to Ally and started kissing her deeply and passionately. Our hands explored each others legs and bodies giving the boys a really nice show. They had quickly removed their clothes and were standing near us at attention. After a few minutes of heavy petting between Ally and me we turned to the boys.

"Did you guys like the warm up?" Ally asked. Both stammered out a YES and looked willing to do anything to participate. I choose Chris and gently taking his lovely cock in my hand started stroking it up and down. I saw some precum emerge from the tip and while looking up into his eyes I used my tongue to lick up the sweet clear fluid.

He had a very nice cock, about 8 inches long with a nicely formed head. I kissed the head leaving a pretty lipstick mark and worked my way down the sides with my lips and tongue. He was now glistening wet and I placed my hands on his hips and took his cock into my mouth deeply. He gasped as the head of his cock reached my throat. I slowly pulled back till just the head stayed in my lips and came down on him again.

"OH OH OH, GAWD...that feels so good!!!" screamed Chris. I just moaned and continued fellating Chris, enjoying the feelings of pleasing a man with my feminine abilities. I glanced over to Ally who was giving Neil a similar experience. She looked at me with a cock in her mouth and one in mine and winked. I smiled at her and sped up my head bobbing while also taking Chris in all the way down my throat. After two or three plunges I felt him tense up and grow in cock size.

Chris screamed, "OH OH I am going to CUM girl!" as the first batch of cum was released deep inside my throat. I pulled out slightly as he continued to pump warm cum into my waiting mouth. I milked him dry taking in all the spunk Chris was able to produce. It was only my second performance and I enjoyed it completely...I felt so girly doing so and loved the power I had making a man so horny and causing him to cum.

I pulled my lips off of Chris' cock and swallowed the cum in my mouth. I also wiped the cum that was on my lips with my fingers and then licked them clean. I grabbed Chris shrinking cock and squeezed out the remaining cum and let it drip into my mouth, then took him into my mouth one last time for a final cleaning. I had to admit to myself that I really loved this part of being girly, it felt erotic, sexy and fun all at the same time. I loved seeing my pretty painted nails wrapped around a stiff cock milking it of its juice. I sucked deeply then let Chris pop from my lips,

"Did you enjoy that sweetie?" I asked.

"That was fantastic girl, one of the best blow jobs of my life!"

"I am glad you liked it because I certainly did!" I looked over at Ally and saw that she had finished with Neil just after I completed Chris. Ally got up and came over to my side and kissed me. To my surprise she had a nice mouthful of Neil's sperm inside and we proceeded to pass it back and forth between us. I noticed Chris and Neil quickly regaining hardness as we continued our kissing and sharing. I had really developed a taste for cum and the kissing with Ally added to the taste.

The guys were definitely done in the orgasm department but very appreciative of our efforts. We kissed them good night and they went back to their rooms to sleep and dream of the blowjobs they recieved. Once they were gone, I grabbed Ally and told her of my plans to go full time. She happily agreed to help me get ready and to go shopping with me for some appropriate (and un-appropriate) outfits for the next few months. To be continued.....

Published 
Written by Picone
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments