Lesbian It Started at Halloween Party

"Honey, it's time to start preparing."

"OK. First, I need to take a shower and then I'll help you."

Lara entered the bathroom and I knew I had half an hour before she'd be out.

It was Halloween and we were invited to a big party at the house of our president, Cliff Hoffman. He ran the company with an iron hand, but the success in bringing us to where we were, earned him admiration from everybody. We were now among the top 3 in New York. Officially, I was never introduced to him and saw him from afar only twice before. He was a big guy, about 40 years old, 6'3", 210 pounds. For all I knew he was not married.

It was the first time Mr. Hoffman organized such a big party for his employees and every one of us wanted to make a good impression. About 40 employees and their mates were invited and the instruction was for everybody to wear a costume. Lara and I decided to switch roles. She would dress up as a man, and I'd be a woman.

My wife, Lara, is pretty, 5'8", 150 pounds, blonde with soft, blue eyes. She is taller than me by an inch. Our body habitus is quite similar, except for her gorgeous C-cup breasts. So we assumed I'd find something to wear in her closet, and she'd select clothes from mine.

The first problem I encountered was my hairy body. It was obvious I needed to shave not only my fast growing beard but other parts of my body as well. The question was how much. I drank a glass of Chardonnay as I waited for Lara to exit. Sitting in the living room, I thought that making a good impression at the party might help me get the promotion I deserved. I selected a short black dress, a pantyhose, and 3" heel black shoes.

When Lara came out and saw my choice, she laughed, "Jerry, to look good in these, you'll need to shave not only your face and neck but also your legs, arms and chest."

I thought about it and decided to do it anyway. I used my electric shaver. However, traces of my brown hair were visible on my hands and legs. I was determined to look better, and in 20 minutes I shaved manually both legs and arms. Next, I used the razor on my chest, careful not to injure my nipples. When I was done, I showered and close shaved my face and neck too.

I reentered the living room and saw Lara selecting her costume from my closet. She saw me and giggled, "Your arms, chest, and legs are fine, but the face will need a lot of makeup."

I measured the black dress. It was slightly tight on my waist, but not bad. I removed it. Lara brought me one of her padded bras. She inserted cotton balls into each cup, and I placed the bra on my chest. It seemed OK to me. Then I tried the pantyhose. The size was fine, but Lara recommended adding hip enhancement pads. I never knew she used them. Her hips looked perfect to me. She placed them for me, and I had to admit my hips looked much more feminine.

Next I tried the dress again. There was a noticeable bulge in my crotch. My penis is average size at best, but the tight dress accentuated this part. I used large band aid to tuck my dick backward, and the dress fitted perfectly. The black shoes were slightly small. I was determined to wear them anyway - Suffering a couple of hours to impress the boss seemed like a good idea.

Lara put a generous amount of makeup to cover my beard and even added mascara. Next, she applied red-hot lipstick and gave me a brown, shoulder-length wig to put on my hair. When we were done, I glanced at the mirror, and was impressed. I looked better than I hoped for!

Lara used a long-sleeved shirt, khakis, one of my smaller jackets, and sneakers. She tied her long blonde hair in a bun, and hid it under a hat. As she worked on her costume, I tried to walk on the tall shoes. I was clumsy and almost fell twice. After few more tries, I succeeded in walking better, feeling my hips sashayed... I smiled and continued strolling using small steps, imitating my wife's walk. By the time Lara was ready to go, I felt better in my shoes.

As we were leaving, Lara joked I looked so good that she was tempted to have lesbian sex with me. We laughed. Minutes later we were on our way. Lara told me it would be better to use different names when we were at the party. We agreed that she would be called Ron and I'd be Gayle. She also reminded me to to talk in high pitched voice and even falsetto if needed.

The Front door opened by a guard who let us in. There were already 20 guests there, all of them wearing costumes. Five of them I didn't know. Mr. Hoffman was easily recognizable because of his height. He dressed as a mid-evil era knight and had mask on.

He stared in our direction as we approached him and said in a deep voice, "My name is Sir Galahad. And yours?" I answered using soprano voice, "I am Gayle, and this is my husband, Ron."

Mr. Hoffman smiled broadly, "Nice to meet you two. On your left there is a bar. Grab something to drink. The food will arrive soon, and will be on 2 corner tables, so you can eat whenever you feel like it.

Lara and I began sipping our wine when a band started playing. Our glasses emptied and Lara winked at me, "Gayle, will you dance with me?"

I chuckled, "Yes, my dear husband. If you insist..."

We joined 5 other couples on the floor. Lara attempted to assume the man's role and twirled me a couple of times. With my high heels, I was lucky not to fall on my face.

After the second song Mr. Hoffman cut in and asked me, "Pretty lady, may I have the honor?"

I grinned at Lara, then turned to the boss and mumbled in a squeaky tone, "I'll be happy to Sir Galahad." It was a slow. Mr. Hoffman put my hand on his waist as his muscular arm hugged my back. Initially, I was concerned I'd screw up, but slowly I felt better. He led me around, and I noticed his arm moving me closer to him as it gently caressed my back. In the next song, he gingerly pulled my head onto his chest, and his hand moved up and down on my back, at times reaching my upper butt. I felt safe in his strong arms, and was sure I was not going to trip. In the beginning, his manly smell which was a mix of his body odor and expensive deodorant felt weird, but in the second dance, I started liking it. We danced a third song, and he whispered in my ear, "Gayle, you are very pretty. I like you." I used the high pitched voice again, "Thank you, sir. You look very handsome yourself." As we continued moving on the floor, he pulled a small piece of paper and stuck it in my hand, saying, "This is my phone number. Please call me tomorrow between 6 and 8 pm."

I murmured, "OK." We separated after the 3rd dance.

For the next hour Lara and I stayed together. We ate and later met Sean and his wife. We drank more wine and talked about sports and politics. Throughout the rest of the evening, Mr. Hoffman didn't even once gaze in my direction. Before leaving, we wanted to thank him for the pleasant party, but we didn't see him. We left at 11:30 pm feeling somewhat lightheaded, likely under the influence.

We arrived home before 12 o'clock. Lara went to the bathroom. I found Mr. Hoffman's note and put it on my dresser. When Lara exited, I went in. By the time I came out, Lara was asleep. I fell asleep soon after too.

The next morning I woke up early. Lara's eyes were still shut, and her respiration suggested she was having a dream. I grabbed a sandwich and drove to work. It was a busy day. I returned home at 5:30 pm. Lara was out. She left me a note saying she went to her friend Barbara, and my dinner was in the fridge. I just needed to warm it in the microwave. As I warmed my meal, I discovered Mr. Hoffman's note.

I called his number. He answered, "Hi, this is Cliff. Who is it?"

I said using my usual voice, "This is Jerry, sir. You told me to call you."

His voice changed, "It must be a mistake. I never asked a Jerry to call me." Then he hung the phone.

I called him again, this time using a high pitched tone, "Mr. Hoffman, this is Gayle. You wished to talk to me."

His tone became softer, "Gayle, it's a pleasure to hear your voice again. I wondered, can you come to my house again tomorrow afternoon at 5?"

With my soprano voice I replied, "Yes sir."

Before hanging up the phone, he added, "I'd appreciate if you could wear again the same clothes you had on at the party."

His request sounded unusual and even bizarre. Lara wasn't around to discuss it with her. I thought about it and after half an hour decided I'd do it. After all, Mr. Hoffman was the big boss. If I wanted to be in his good graces I'd better do what he wished. What harm could happen?

Lara arrived late. I was watching a basketball game with the Knicks and the Lakers. The score was very close. I held my breath and ignored Lara as she headed to the bathroom. Later, during a break, she saw me and blurted, "Tomorrow afternoon, I'll be at Barbara again. We are preparing a surprise party for her husband's birthday."

I answered half-heartedly, "OK."

The game ended 40 minutes later, with the Lakers winning by 5 points. Good!

I slept like a baby.

The following work day was a normal one. I finished at 4 pm. As she mentioned in her note, Lara was out. I had an hour to dress up like Gayle, this time without Lara's help. Fortunately, the party's clothes were still on a hanger nearby. I shaved again, showered and put on the bra, the hip enhancers, the pantyhose and the dress. Then I tried my best to put on makeup, mascara, and lipstick. The result was not as good as when Lara did it for me, but still reasonable. I wore the black shoes, placed the wig and was ready by quarter to 5.

I drove to his house, wondering what were Mr. Hoffman's intentions. By now he must have known who I really was and that I was married. Was it some kind of a game?

I parked my Honda by the front door and rang the bell. Mr. Hoffman opened the door himself. He wore a long robe, and welcomed me with a smile, "Gayle, you look smashing! Come on in. I'd like you to taste the cocktail I just made according to a special recipe from New Orleans."

I sipped it. It tasted sweet and tangy. I liked it and grinned approvingly. He led me to the living room, where soft music was playing and said, "Dancing with you the other night felt very good, and I invited you back wanting to repeat the pleasant experience."

His reason sounded ridiculous to me, but he was the boss, so I didn't laugh.

As I continued sipping the tasty cocktail, he guided me to the center of the room and began dancing with me. His strong hands held me as we moved to the sound of the slow music. After my initial hesitant steps, I relaxed against his muscular torso. Mr. Hoffman noticed my glass was empty, and while continuing to lead me on the floor, reached the table and filled my glass again. I chugged the sweet stuff and leaned my head on his broad chest. By the third dance, I was feeling happy, but was slightly dizzy, and hung on his robust hands.

He noticed that I became unstable on my legs and helped me to the nearby sofa. I smiled at him and closed my eyes for a moment. He hugged my shoulder and pressed my head onto his chest. I mumbled, "Thank you."

He lifted my chin tenderly and said in his deep voice, "No. Thank you, Gayle. You are very pretty." With my eyes still shut, I continued smiling at him. Next I felt his lips lightly on mine. His head moved back before I was able to react. In my foggy brain, his action felt weird yet not unpleasant. I kept my eyes closed. He kissed me once again this time harder, forcing my lips open. It took me some time to grasp what was happening. By the time my mind finally got the message, his tongue was already dancing in my mouth, looping my own tongue, and sucking on it lightly.

I was never kissed like that before by Lara or other girls. I've never kissed a man either. His unexpected move took me by surprise, but the alcoholic drink affected my ability to comprehend and react. His demanding kiss was somehow reassuring, and I did not disconnect. My hands hugged his chest, clutching to his body.

Subsequently his mouth disengaged from mine, and he whispered, "Gayle dear, I really like you." I leaned back on the sofa, keeping my eyes closed with a delighted expression on my face.

His right hand continued hugging my shoulder. Then I felt his other hand caressing my cheek. It moved down to my neck and later descended to my chest. His huge palm cupped my fake breast. Deep inside, I was sure he could feel it was fake so it must have been some kind of a game. I grinned.

Next he placed his right hand on my cheek, and his fingers trailed softly over my face. It was somewhat ticklish but pleasant. I kissed his fingers one by one, until I reached his thick thumb. He pressed his thumb onto my lips. I spread my lips and his thumb penetrated, lightly rubbing against my palate. I sucked on it. He bent toward my ear and whispered, "Good baby. Do you like your new pacifier?"

I couldn't talk but nodded 'yes' with my head. It was really wonderful, calming feeling. My semi conscious mind told me I was safe in the arms of my protector and that nothing wrong would happen to me. And I liked my new pacifier.

Mr. Hoffman's other hand continued massaging my body gently for a while, and then stopped. I wanted his hand to continue caressing me and arched my back, hinting at my wish.

He chuckled and blurted, "Just a moment dear. You'll get your wish soon." I vaguely heard an unzipping sound, but concentrated on enjoying his huge thumb slowly probing my mouth.

Shortly after, he whispered, "Honey, I brought you a toy to play with." My eyelids felt heavy and refused to open. I kept smiling. Next his left hand grabbed mine and gingerly pulled it toward him. Few seconds later he placed my palm around a big, warm hard organ. It was velvety and pulsatile, and felt like an erect penis, but it was humongous!

I never touched another man's dick. My brain tried to tell me it was wrong, but it felt smooth and velvety in my hand, and I kept holding it. I attempted to wrap my hand around it, however, it was too thick.

I heard Mr. Hoffman's voice, "Baby, it's yours. You can play with it now."

While continuing to suck gently on his thumb, my hand began exploring the massive tool. The base was hairy and started just above a heavy ball sack. I jiggled gingerly the giant testicles, thinking they were at least twice as big as mine. The shaft was rock-hard yet soft and veiny on the outside. The mushroomed head was huge and spongy.

I tried again to open my eyes but did not succeed. I gave up.

He guided my hand to bob his pole. It continued engorging in my small palm and felt good. A short time later his hand moved away, and I continued bobbing by myself.

"Honey, do you like the way my cock feels?"

I nodded 'yes' and massaged it slightly faster.

He whispered, "Gayle darling, You'll always be MY baby, but you are actually a pretty LADY. Women no longer use babies' pacifiers. They switch to better, adult-sized things. Here, try it. I am sure you'll like it."

Subsequently, his hand slowly pulled my shoulder in his direction and then lowered my head down. Soon my head landed on his lower tummy, and I felt his warm pecker touching my lips.

I hesitated and sniffed it. It smelled soapy-clean, and musky. I licked it lightly and it jolted. I licked the top again and felt a slightly salty liquid on his slit. I liked it and continued licking it.

From a distance, I heard Mr. Hoffman laughing, "Yes girl. Enjoy your appetizer. The main course will be served soon." His hands slowly shoved my lips onto the spongy head. My brain was still in a haze when my lips parted to accept his present.

The more his member penetrated, the wider my lips stretched. When I was about to scream that they'd rip, his rod popped inside, and the outward pressure on my lips diminished.

It felt like an enormous piece of meat was lodged in my oral cavity, pressing my tongue to the base of my mouth. It felt too big for my mouth but I was grateful the shaft was somewhat less wide than the head. I thought about how Mr. Hoffman's girlfriends were able to perform a blow job on such a huge organ...

I had little time to think, because seconds later, I felt this lump moving gently in and out inside my mouth. Fortunately he didn't try to pull it out completely and reinsert it again. But then, he started gingerly pushing it forward. Barely 3" were in when I began gagging. He whispered, "Baby, relax your mouth. Don't fight it. Let it in."

I wanted to tell him I couldn't but my voice was blocked by his member. He attempted to advance forward, but after an additional 2", I choked and coughed on his tool. My saliva was leaking badly around his pecker. He stopped in his tracks, caressed my cheek, and blurted, "Gayle honey, take it easy. I am not going to move further. Breathe slowly with your nose, and you'll feel better in a jiffy."

I tried to do what he suggested, and gradually I felt better. The choking feeling abated, and my normal respiration resumed. The giant object in my mouth was still exciting my glands, and my saliva was pouring onto his tool, but somehow my mouth accommodated it, and I relaxed. My head was still in a daze. I felt like floating in the air and watching myself from above. I rested my head on his lap.

Next, I heard him say, "Honey, I am happy you feel better with your new pacifier. Now be a good girl and milk it for me." I sucked on it mildly.

"Not like that. Suck it harder."

As my lips and tongue applied more pressure on his steely hard organ, He began moving gently in and out, and his hand pulled mine to massage his hairy ball sack. I did it for about a minute before his torso tensed. His hands closed behind my head, and suddenly a river began streaming into my throat. The first few drops landed in my larynx, and I started choking again. He retreated slightly, allowing my tongue to stop the flood from reaching my airway, and I managed to swallow his large load.

After what seemed like a year the stream became a trickle, and swallowing the slimy liquid became easier.

Gradually, his dick deflated. Mr. Hoffman kept my head in place, and his raging cock shrank into a 6" soft hotdog. His shriveled prick was still longer than mine when erect, but since it was soft, handling it in my oral cavity became much more tolerable, and even pleasant.

My eyes were closed throughout the ordeal. Now with his pacifier resting peacefully between my lips, I felt good again. The musky, somewhat oily, and salty taste of his cum stayed in my mouth. To my surprise I actually liked it. I remembered one time at home, I masturbated and later tasted my sperm. The taste was different and less palatable. Now, the more I rolled the remaining slime in my mouth, the better it felt on my tongue. Weird!...

I must have fallen asleep, because I was awakened by Mr. Hoffman trying to move his body under me. My lips still enveloped his shaft. I opened my eyes, and he smiled at me, "Gayle honey. You were great. I like you a lot!"

My head slowly cleared, and I pulled his cock from my mouth. In the last moment, I remembered to use a soprano voice, "How much time I was out?"

"About an hour. But don't worry I enjoyed it. You were dreaming and sucked my dick a couple of times. I was tempted to use your mouth again, but I chose to let you have a good sleep after your brave first oral job."

I sat up and stared at him. He hugged my shoulder and whispered, "Dear girl, I really like you. I do not know much about you and care less about details. By the way, at home, I prefer to be called Cliff and not Mr. Hoffman... I wish to see you here again. I'll be free on Thursday at 7 pm. Please come and meet me. I'll be waiting."

Near the door, he turned my head and softly kissed my lips before letting me go.

My head felt better now. I tried to think about what happened in Mr. Hoff... Cliff's house, and was confused. How did I let it all happen? All my life I knew I was normal heterosexual guy: When I was younger, I dated only females, and now I was married to a wonderful loving lady... I masturbated thinking only about pretty girls. The whole encounter was too much to comprehend while driving. I was too tired.

I arrived home and didn't see Lara. She was still at Barbara's. I undressed, placed my attire in my closet, showered thoroughly and went to bed. Lara showed up 15 minutes later. She removed her clothes, put on her nighty, and after using the bathroom, joined me in bed. She declared, "We worked hard for long hours. Jerry dear, I am going to sleep. She approached me, kissed my lips and commented, "You smell fantastic. Would you like to hump me before we go to sleep?"

I chuckled. When we started dating, she was very shy and was scared to mention anything about sex. Gradually, she opened up and became less reluctant to talk about the subject. In the last 2 years, Lara's bed talk turned more suggestive and overt. The way she invited me to fuck her became a ritual where she used words like pound, plow, ram, and hump. I loved it and admitted that hearing her wish to be drilled aroused me.

I grinned at Lara, "I'd be happy to jump your bones."

Her nighty landed on the nearest chair seconds later. I ogled her terrific body. At 28 she was 5'8", 150 pounds with blonde hair and deep blue eyes. Yes, she was pretty. Her figure was also hot: Her C cup tits stood high on her chest with dark nipples protruding forward, begging to be touched. Her skinny waist continued down into a flat soft tummy and round shapely hips. The mere gaze at her body always stiffened my dick, and readied me to pounce on her.

I removed my underwear, and my hard 5" jerked up. Lara smirked, "Is your weapon about to attack me?"

I didn't bother answering. I jumped between her thighs, lifted both her legs toward her head, and Inserted my dick all the way into her hot pussy. My pecker was not that big, but my sudden, rough move always made her hungrier. Lara spread her legs wider, inviting me to ravage her cunt. I didn't waste time, thrust my organ fast into her hole and continued incessantly. Lara began whimpering as her climax was around the corner. Watching her like that made me hornier. We were both closing in on our orgasms as Cliff's colossal cock appeared before my eyes. It looked thick, graceful and ready to be sucked. That was the last straw for me; I ejaculated my load as deep as I could in her moist vagina. Lara climaxed simultaneously with me.

Minutes later, she raised her upper body, kissed me good night, and grinned, "Jerry, you came like a wild beast. Did I look especially sexy tonight?"

"Yes you did," I lied, "Your body wakes the animal in me too often. Most times, I manage to hold up, but tonight I just reacted differently."

She was asleep a couple of minutes later. I lay on my back and thought about the unexpected appearance of Cliff's cock during sex with my wife. Did it have a special meaning?

On Wednesday, at work, I observed Mr. Hoffman passing me by. I watched his face. He saw me and said nonchalantly hi as if he did not recognize me. Didn't he know I was Gayle, or he knew yet elected not to show it? I could not answer. There was nobody I could share the story about my encounter with him. He stayed close the whole day, and my eyes shifted toward him multiple times. His imposing body looked magnificent compared to the other much shorter and chubbier employees who surrounded him.

Unlike Lara my very feminine wife who I loved, Cliff was a big, handsome male who oozed manliness. His presence hypnotized me and attracted me like a magnet. I knew then that the following evening, I'd be again at his house.

Thursday after work I told Lara I promised Len to watch the Lakers vs the Jazz basketball game with him. She giggled, "Two men bonding together is always a good thing." If she only knew...

Unbeknownst to her, the clothes, shoes and even the cosmetics box were already in the bag I planned to take with me. At 6 pm, I went to the health center I was using twice a week. I entered the men's area, and dressed in one of the showers' booths. I used a small mirror I found in the box to adjust the makeup and lipstick, then waited a couple of minutes until the area was quiet, and hurried out. As I exited the men's dressing room, a regular customer who I talked to before, smirked at me, "Lady, unless you were here to ogle nice cocks, next time use the ladies area."

I felt relief he hadn't recognized me and didn't respond. I drove to Cliff's house and arrived 10 minutes late. He opened the front door wearing a different robe and said, "You are late. I was concerned you won't show up."

I stuttered, using my Gayle's voice, "Soorry Cliff, but I haad to solve a prooblem before coooming here."

He moved to the sofa and said nothing. I sat by his side and looked at him. He ignored me, leaned back and closed his eyes.

He was apparently upset I was late. I hugged him, trying to cheer him up, and mumbled, "I missed you." He didn't move.

"Please Cliff, be nice to me." No reaction.

I decided to be bolder. I stood before him, kissed him lightly, and my hand caressed his groin. Slowly, he turned to me and grinned, "You really missed me, didn't you?"

"I did. Very much."

"Show me how much."

With fumbling fingers I opened his robe. Underneath, he was naked! My eyes moved up and down on his athletic body, feeling my own dick steered. My palm trailed from his massive pectorals to his 6-pack, touching lightly his impressive muscles. The closer I came to his gigantic cock, the faster it hardened and rose toward the ceiling.

I engulfed the base between two fingers, aimed it at my face, and bent forward. I opened as wide as I could and managed to wrap my lips around the soft head. It felt good. It was much better than on the first day. Cautiously, I went down on him, maneuvering gingerly to let as much of him as possible in my mouth. This time only 2" remained outside when I began gagging. I pulled out slightly and tried again by relaxing my oral muscles. Another inch got in. I was happy. I started blowing him and gradually increased the speed.

Several minutes later, his respiration became labored and he blurted, "Honey, today your mouth works magic. Be ready for your Ambrosia."

I continued milking his huge pole, knowing his slimy stuff would erupt at any second. As his body tensed, I retreated minimally, placed my tongue on his tip and half a second later, Noah's Flood gushed inside my mouth. I swallowed as fast as I could around his thick pecker. Once it started slowing down I had a sigh of relief. This blow job may not have been perfect, but it was much improved vs the first one. I was less scared, prepared myself better, and swallowed his juice without choking. I cleaned his junk with my tongue, kissed the top, and stared at Cliff's face. He glanced at me and said, "Gayle honey, you are the best cocksucker I ever had. Before you arrived here I thought that if you showed motivation and initiative, you'd deserve a present. So I went to a jewelry store and bought this for you." He pulled a small box from one of the drawers, and gave it to me.

I opened it and saw a necklace made of gold chain and decorated with a pinkish-purple transparent stone. I stared at him, not knowing how to react. He French kissed me and then whispered in my ear, "It's amethyst on a gold chain."

I hugged him tightly and murmured, "It is very beautiful."

Cliff smiled, "If my baby continues behaving nicely, she'll earn more prizes."

I whispered, "I love being your baby."

He took my hand in his and led me to a small closet. He opened it and said, "Last time when you slept on my lap, I checked the labels on your dress and shoes. Yesterday after work, I went to Macy's and bought several sets of clothes and shoes I thought would fit you. You can select your next attire from this closet."

I sat on his lap, faced him, kissed his lips lovingly, and mumbled, "Cliffy, you are too good to me."

He grinned and asked, "Will you be here again Sunday evening at 8 pm?"

"I'll try, but I cannot promise. My relatives are coming from out of town to visit."

His expression turned sad, "I was hoping..."

I caressed his cheek, "I'll do my best but I won't be able to stay long."

He smiled, "This will be great. See you then."​