A Classic Car Changes My Life

Hi, my name is Jack 30-year-old bi-dominant male. My wife Dot is gorgeous,35 years old. Also, bi, she is a switch. Our marriage is open. We have agreed only to meet people of the same sex. We have no children and love each other deeply.

Today we are hosting a bbq, for some friends and neighbors. About 25 people are in attendance, primarily couples our age but a few younger and some older.

Among the guest is Bob, a retired teacher, he lives alone about a half-mile from us. He tends to drink a bit too much, appears out of shape, with a bit of a beer belly. Short, about five feet six,

I singled Bob out. Handing him a fresh beer, we exchanged small talk while he drank. I gently swerved the subject to a car he had tucked away in his garage, A 1965 GTO convertible. A beer later, Bob had informed me that he was interested in selling the car, He would gladly show it to me tomorrow, and we could work out a price, I beamed, I had been coveting the car for weeks, now its within reach,

Bob noticed the joy on my face. He smiled and put his hand on my shoulder. Then told me that the price might be a deterrent. I almost let out a gasp as his hand clutched my shoulder. It was like he reached in and touched my soul, creating excitement, fear anticipation. Sending a shiver through my body, His hand lingered for a moment then brushed down to my chest before going back to his side. I did my best not to appear fazed, but my reddened face and the bulge that was building gave me away. Bob noticed but said nothing except asking If I was ok.

Bob started walking away, ordering me to come up early tomorrow morning that he starts his day early. As he drifted into a group of people, another shiver went through me.

An hour later, there was a commotion, rushing to see what was happening. I saw Bob sprawled on the ground. Looking up and grinning, he stated, "I guess the beer` is taking hold of me,"

I helped him up, asking if he was ok, Assuring me he was but, he asked for a ride home. Helping him into my car. I drove the half-mile to his house. Guiding him out of the car and into his place was tricky. He was stumbling all over his hands, flopping against my body. He even groped my dick,

Settling him on his couch, he relaxed. I removed his shoes and had him lie down. Fetching a glass of water and putting it on the coffee table, I found a blanket, making him comfortable.

"Ok, Bob, you need to rest. Take a nap then if you feel ok. go up to your bedroom."

Reaching for my hand, squeezing it, thanking me telling me not to forget about tomorrow morning.,

Back home, we cleaned up after the party. I mentioned to Dot about the sensations Bob sent through me just by touching me,

"Oh, honey, you are just excited about the car. Besides Bob is an older man. You could let him give you a bj. Mabey he would lower the price!" We finished cleaning up and went to bed, enjoying a session of sex before sleep,

Waking in the morning, I showered, shaved, slipped into a pair of sweats. Then walked up to see about the car,

True to his word Bob was up, drinking a coffee when I arrived. Accepting a cup, we sat and talked, Bob told me he had a price of five thousand dollars in mind, but we could negotiate, finishing the coffee we stood Bob`s robe opened. I almost gasped out loud when I caught a glimpse of this cock. It had to be eight inches, in its soft state,

Bob apologized, smiled, telling me he rarely wore underclothes around the house. We went to the garage. Inside was the car of my dreams, All dusty but no rust. I thought was all it needs is a good cleaning,

Bob suggested opening the hood and checking out the engine compartment. It released and opened easy, revealing a legendary 389 cu inch motor. Walking around the car the I looked it all over with Bob right behind me,

He pointed to a spot under the radiator and asked if it was a leak. I was looking to see if it was a leak. I felt Bob push against me, his cock rubbing my ass through my sweats. At the same instant, his hands went under my waistband and grasped my cock,

I let out a surprised "what the" as his hand rubbed my quickly hardening dick.

He worked my shorts down as he continued stroking me, I have had men jerk me off before, but for some reason, this man touching me made my mind go blank,

He continued stroking me while his dick rubbed against my ass cheeks. He stroked me for a few min whispering in my ear, "go ahead son shoot your load. You love this," then Bam, my load exploded on the fender of the car. He continued to massage my dick till my knees started to buckle. His cock now hard, rubbing between my butt cheeks.

Catching me his arms under my armpits, his hands cupping my breast`s Bob fingered my nipples, exciting me even more. My cock remaining hard, and involuntary moan`s escaping my mouth. Removing one hand, he scooped some of my cum off the fender. Holding the cum-coated finger to my lips, he told me to taste it

"No, I replied, I don` eat my cum."

"Well son this will be a new experience that you will enjoy. He forced the finger between my lips, holding it there till I cleaned it off.

Bob kissed my neck then said, let`s go inside and get the deal done,

Bob strutted toward the house. I followed my legs weak, and my mind scrambled. Once inside, my mind cleared, stopping Bob before he went up the steps. I told him that I am bi, but I am a top only. I let people blow me or fuck them. That I set the terms for my sexual encounters.

Ignoring me, he leads me up the steps to a desk in his bedroom. The room was huge with a kingsize bed, all very neat and clean. We sat on wooden desk chairs as Bob wrote the bill of sale going onto a drawer brought out more paperwork for the car,

Handing me the paperwork to read, he stood up and walked behind me as I read. I could feel his hands rubbing my shoulder. My mind was starting to cloud again. I could barely keep my mind on the paperwork. I asked him to stop touching me,

"Your so sure you are a top," he chided me. You are enjoying what I did to you. Perhaps you are not all top?" "If you are not scared, come over to the bed. I will show you what you want to be."

Curious, I followed him to the bed, we sat on the edge, Bob removed my shirt and pushed me back on the bed, I repeated I was a top only, but he simply grinned, then he started working my nipples, squeezing them rolling them between his fingers,

My eyes closed with pleasure, a moan flowed from my mouth. "Stretch your arms over your head and experience a stronger feeling," Bob told me,

Stretching my arms above me, I felt Bob shift Then heard click s as cuff`s captured my wrists,

"What the hell. stop this, take them off," I shouted,

Bob ignored me, arousing my nipples, using one hand on them and the other stroking my cock. Squirming with the pleasure I was feeling, on the edge of another orgasm when Bob stopped.

"you see what I mean son? You love being treated like a bottom, actually a sissy bottom, and This is your deep desire,"

"No, I am not a bottom or a sissy," I said, my voice wavering, showing signs of doubt,

Bob removed his robe, his cock hard, now had to be 11 or 12 inches long and very thick,

"You will now learn how to satisfy a Real top. and experience your true calling."

Pinning me on my back, my hands still cuffed to the bed, Bob positioned his dick about an inch from my lips, then forcing the head into my mouth. He stated that all sissy bottoms know how to suck cock instinctively,

I have sucked a few dicks in my time and thought if I could get him to shoot his load quickly, I could get out of this situation. Applying all my knowledge, I licked and sucked the large cock head. I heard a moan and thought he might be close. Seconds later I felt him pushing more of his shaft into my mouth enough that the head entered my throat, Gagging and squirming my eyes watering, I almost passed out till Bob pulled out, allowing me to catch my breath and gain some composure,

"You need to do better than that, sissy!" breath through your nose and relax this time,"

Shoving the huge cock in my mouth again, he slowly pushes into my throat, then worked it in and out,

I gaged a little but did as he said and just hoped he would cum. Without warning, the cock was pulled out of my mouth. Relief poured through me,

"Not bad sissy, you had almost half my cock in you, and you did a fair job sucking it. With practice, you will become a good cock sucker."

Getting off me, he rolled me over, then opened a bottle of lube. Bob spread the cool liquid on my ass."No, please don`t. I am a top. I have never been penetrated by a dick before!"

Bob went to a dresser returning with a ball gag, securing it he said that he hates loud winey noises and that this is going to happen, so relax and accept it,

Panic overtook me thinking that his dick will tear me apart. I would end up having to go to the hospital, emergency room.

Feeling pain as he worked a finger into me, then two, a third one, more lube the fingers penetrating, stretching my tight ring, slowly the pain left, and the feeling became pleasant,

The fingers were removed and quickly replaced with the head of his cock. My stretched hole accepted it with hardly any resistance, the head resting just inside my hole was almost soothing,

Bob pushed slowly in pain returned, I was sobbing as the intrusion continued, it stopped when I felt his balls touching my ass cheeks,

Remaining still letting my ass adjust To Bob`s dick, he told me the worst is over. Now he was going to fuck me, breeding me with his seed, making me his.

fucking me slowly, using the total length of his dick, I found myself starting to enjoy the feeling, and every movement stimulated my prostrate, gasps and moans flowed from my gagged mouth, as my cock spurted another load of cum into the sheet.

"You like being fucked like a pussy don`t you?". "We are going to have so much fun together, my little sissy."

Bob fucked me hard and long, at least a half-hour, the pleasure I was feeling made me doubt my masculine role,

Feeling Bob`s dick pushing harder into me as he pulled my ass to him. Cum filled my ass. Bob collapsed onto my back. Regaining his composure and breath, Bob ran his fingers through my hair. Speaking almost with love in his voice, he told me I was now his sissy toy,

pulling out of me as he stood up. My mind experienced sadness, missing the huge dick that had taken my cherry. My gag removed Bob gloated; You pleased me while you enjoyed doing so.

He released me from the cuffs. I was so weak that I could only lay there, my ass leaking cum, my mind not understanding why I felt this way. I was Jolted back to reality by Bob`s voice telling me to follow him to the shower. I followed submissively, He adjusted the water, and I started to step in. Bob grabbed my shoulder and lectured me, telling me a good sissy never goes before her master. Bob entered, handed me the washcloth and soap, telling me to clean him. After doing a great job of attending to Bob`s body, I was allowed to wash.

Dried and back in the bedroom, I sat on the bed as Bob lectured me on what he expected of me. He also told me, my name is now Jackie, Handing me a list with instructions on what I should wear and how I should treat him next sat when I came back to check out the car, I glanced at it, surprised that he wanted me dressed as a woman,

"We already signed the agreement for the car. Why should I do any of this? you practically raped me, and there is no way I am going through this again."

Taking my hand and leading me downstairs, both of us still nude, he sat me on the couch then turned on the tv. Images of me sucking his cock, then being fucked by him, accompanied by sounds of my moaning, and closeups of my face, a look of pure rapture on it. Turning off the tv, Bob toyed with my nipple. At the same time, he told me that, besides the video, you loved it and will want more,

Jackie, be a good sissy and be here early next Saturday. If you have any problems dressing ask your pretty wife to help. She always dresses hot. I might even see how good she is in bed, Bob gloated.

Not bothering trying to remove his hand from my nipple, probably because it felt good, I told him my wife only fools around with other women. Bob chuckled saying things change Jackie. He then grabbed my head, pulling me to his lips, kissing me deeply,

I struggled; he stopped, "I don`t kiss men!"

"Jackie the old you may not have kissed men, but the sissy you are will, and enjoy it, the same as when you kiss your wife, now let's try that again,"

Our lips met, I half-heartedly kissed back. Bob pleased with the results released me, telling me to be here early next Saturday,

Back in my house, I sat at the table still shaking. Dot asked me how it went? I blurted out the whole story,

"OMG, my husband is becoming a sissy," her face beaming. I wish I could have watched that, did you enjoy it?

"Sadly, towards the end, it did feel good. I have never sucked a cock that long, But losing my cherry was painful at first." What am I going to do about next Saturday and the video?"

"Well Jackie, I mean Jack, that's your decision, You want the car, and you said you enjoyed Bob using you. I would follow through with it. You can always just drop it if it bothers you. What you are experiencing sounds exciting. Don`t worry about the video. He is probably bluffing,

"Yeah, right. I could do another week, then put a stop to it.

Jack, when you go into work Monday, tell them you will need a few days off. I will make all the arrangements to get you dressed as a woman. Oh, this will be fun, you will see.

Dot took my measurements and went on a shopping spree. I took the rest of the week off work, then came home that night to a thrilled wife,

Dot took me by the hand to our bedroom where I undressed.

Dot started giving me things to try on. Everything she bought fit, I had bras, panties, skirts, blouses, different pairs of shoes from flats to 3-inch heels, even pantyhose,

As I tried them on Dot shook her head. "No! this won`t do honey. You need a new hairstyle. You need to get rid of the hair on your body. I have a friend who is a beautician. I am going to see if I can get a private appointment with her,

Dot ignored my protests as she called her friend, setting up an appointment for tomorrow. after the call Dot asked me to put on the undies and a maid outfit she bought. Looking me over, she removed pads from a bag and inserted them into my bra, "There, honey, that gives your figure a more feminine look, not big but enough to shape you. " "Now let's have sex. I want to make love to you as the woman You are becoming.

The sex that followed was exhilarating, Dot had two major orgasms, and I enjoyed being dominated by her.

The next day we went to Dot`s friend`s shop. I was a bit surprised to see cars parked in the lot and people inside when we entered. Dot Introduced me to Alice. I was being seated in a chair for my hair wash. Cleaned, Alice led me to a chair, my hair styled. Then In another room, Alice asked me to remove my clothes.

"for what? " I asked.

"For your wax job sweetie," came the reply,

Removing my clothes, and surprising Alice, when she saw me in bra and panties,

"Cute," she replied but everything off, then on the table, the following three-quarters of an hour consisted of pure pain. Both women enjoyed my cries of anguish, finished with my front, I laid on my stomach as they continued, working from my neck down; they were soon at my ass. Pasting and peeling, without warning, I felt a finger invade my hole. A second finger followed. I moaned, enjoying the sensations. "This ass is just begging for my strapon, Alice said, rubbing my hole.

"Sorry girlfriend, Jackie er Jack and I have an agreement, to only date same sex, people," Though you have given me an idea.

Slapping my ass telling me too bad you are missing out. Alice told me to dress. Then she gave me a pedicure and manicure. When she finished, my nails and toenails painted a bright red.

"Now for the makeup. Both of you pay attention to how this goes on.

Finished, Alice admired her work before leading me to a full-length mirror.

Starring at the Image, I could not believe it was me. I would pass for a woman almost anywhere,

Alice hugged me, squeezed my butt, telling me not to forget her.

Back home, Dot was happy as hell, "Honey, you look so hot. Tonight we are going on a date. Dot and Jackie, and tonight I am in charge. so first thing let's get you dressed, then we will go out for dinner."

"Dot, let's not get carried away; this is just a means to an end," I said.

"Yea right Jackie, now let's hurry. I am hungry," Dot said with a hint of sarcasm and a slight smirk on her pretty face.

We ate at A nice restaurant. Dot had dressed me conservatively, and a white blouse and a black mid-length skirt with nylons. I have to admit the clothes felt good next to my now smooth body. We stopped for a drink Dot ordered. We sat at a quiet table. During the next hour, both of us were approached by men trying to get to know us better. I sat through it with a blank expression as Dot explained we were a couple. During our alone time, she commented that we could have our pick of all the men here, a gloomy "whoopee" was my reply, but my mind was actively checking the men wondering what their dick`s would feel like inside my hole.

Back home, we got ready for bed Dot told me to leave my makeup on and change into a nightie she had bought for me. I started arguing but thought, screw it. I need sleep. Dot came out of the bathroom nude. I could see her breasts and a harness with a strap-on rubber dick where her pussy was in the dim light.

"Ok Jackie time to play!" I have been thinking of nothing else but fucking your little butt since Alice gave me the Idea." Not listening to my protest, she crawled into bed using her charm; I melted in her hands.

She lubed up her fake dick then spent time lubing and fingering my hole. Her fingers were gentle. She turned me into a cock craving whore full of lust in no time.

"Please Dot if you're going to fuck me with that dildo do it. I was begging, Adjusting myself; I was kneeling my head and shoulders against the mattress, my ass exposed for dot to use.

Good girl now here comes the good part." Dot aligned the head and pushed. The feeling was different than Bob`s cock; it wasn't as large, but the results were the same A little pain and then Just the heavenly feeling of a dick fucking my ass. Dot informed me that this was the same one she used when she and Alice played. Dot was perfect; she had me on the edge of cumming a few times. She was excited and definitely in control,

She continued drilling me till she let out a gasp, then pumped slowly for a min.

"Oh, Jackie I just had the most wonderful orgasm. You Just excited me so much. Now I better let my little girl experience her release." Reaching around grabbing my cock, she continued fucking my ass while jerking my dick, I came with a gush, shooting on the bed and her hand, Pulling out of me and removing the harness, she stretched out on the cum soaked bed, I laid next to her both of us content.

I spent the next day learning how to apply makeup and how to walk in heels. Watching Dot`s face glow, I knew that Dot was as Excited about my sissy, submissive side as Bob.

Saturday arrived, rising early, preparing for the meeting with Bob. Dot helped me with the makeup and dressed me in a provocative outfit. I thought about just wearing slippers. Dot told me walking in heels would be good practice, Kissing her goodbye, and walking up the street to Bob`s house dressed as Jackie felt almost normal.

I walked into the house. Bob was seated at his table, with his robe on. The look on his face when he saw me was one of amazement. Standing up, motioning me to him. His hands were gently feeling my body. His first words spoken were, "OMG Jackie you are beautiful. Your wife has excellent taste, a kiss followed, I tried to put emotion into though I didn`t feel attraction, the praise made me feel wonderful, the kiss broke, and I felt a hard dick pushing against my skirt. I reached down to stroke it. A pleased look appeared on Bob`s face.