The Boss’s Son Ch. 04

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Jackie takes Terry as I watch.
2.7k words
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Part 4 of the 6 part series

Updated 06/11/2023
Created 03/20/2022
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kparc1212
kparc1212
926 Followers

Chapter 4 The Wife's Turn

***

Explain to Jackie? How was I going to explain what I had just done for the past four hours?

First things first. I had to change. Myself, my suit reeked of sex, perfume and sweat. My white shirt had makeup stains.

Twenty-minute drive to my house, send those reports to Andrew. A quick shower, get dressed, back in the car, forty minutes to work.

When I got to the house, first things first. I sent the reports to Andrew. I then went straight up to our bedroom. I stripped off my clothes, threw my dress shirt and under clothes into the hamper and stuffed my suit in a bag in the closet. I made a mental note to take it to the cleaners over th weekend. Cleaned suits, tell no tales.

Quick shower, quick dress, out the door in 20 minutes, at the office at two.

I breathed a sigh of relief when I settled into my desk chair and my assistant read off a list of items and calls that needed attention. I didn't hear a word she said and told her just to leave the info on my desk and I'd get right to them. I then shooed her way.

Trying to concentrate on business the rest if the afternoon was next to impossible.

A little after five, I texted Jackie and said I'd meet her at the car to head home. As soon as we got into the car Jackie asked why I hadn't answered her texts and what took me so long. I fumbled fir answers, I didn't know my phone was on silent, traffic was bad, there was an accident, I couldn't find the disks. I basically came up with as many tales I could think of. Anything but the truth, that i sucked off the boss's son and fucked him.

Jackie had an expression on her face that seemed to saying, "What?" Then she squinted, gave me a serious look, turned and stared out the windshield. We rode home blissful silence. I just thankful I wouldn't have to keep making up excuses for my five lost hours.

When we got home, we both headed for our bedroom to change. I threw off my suit jacket and slipped out of my shoes, as Jackie made a beeline for the master bath. I had my suit pants down at my ankles when she stepped out of the bathroom holding my white makeup stained white dress shirt that I had thrown into the hamper bag. We have a laundry service and I didn't think anything of just putting it in their pickup bag. Didn't think, was right!

Jackie stood there in the bathroom doorway, glaring at me, angrily asking, "Want to explain this? In the car I noticed you'd changed your suit and you are now wearing a blue shirt. So, who's makeup is this, and although I do like her choice of perfumes, I'd like to know, who the hell is she?"

I must have looked a site, the proverbial husband caught with his pants down. I stood there wide-eyed staring at Jackie holding my stained white shirt.

"Well, Robert, who is she?"

My mind was racing. How do I answer? She? The reality of what I had done set in. No way out. Fuck me.

Anger and frustration in her tone, "I'm waiting. Some girl from the office? Who is she?"

I blurted it, "It's not a 'she'."

My words startled both of us.

She got a quiz like look on her face as she stared at me. Then, like a light bulb going off in her head, recognition. She was putting everything together. At the boss's house, gone for hours, not another woman.

Jackie looked at me, astonished and loudly asked, "Terry? You were with that boy?"

I stood there, with my pants down unable to speak and nodded, 'yes.'

Jackie smiled, "Pull your pants up, we're paying your boss's son a visit."

"What? Wait? Going where?"

"Just shut up, pull your pants up and put on your shoes. I want to have a little chat with your lover."

I obeyed. What choice did I have?

Back in the car the inquisition started. "So, what did you two do?"

I just stared at the road as I drove. My mind trying to comprehend how my life had changed.

She continued, "Did he suck you off? Oh my God! You had makeup all over your shirt! Was that precious little boy made up like a girl? Is this your first time with him? Did suck him off?" Jackie kept talking at me, not waiting for an answer.

"Well Bob, tell me what you guys did? What was he wearing?"

This time she stopped the rapid firing questioning and looked at me waiting for my reply.

I sighed, "He was wearing one of his mom's dresses. A backless, black, sleeveless dress that showed off most his legs. Sheer black, back seamed stockings with three-inch heels. His makeup made him look stunning and I..."

I looked at Jackie. Her mouth open. "Oh my God. Was this your first time with him? How long have...?"

I interrupted her. "This was the first time. I didn't plan it. It just happened. I'm sorry."

Jackie turned and looked out the windshield, surprising me by stating, "I'm not. Now it's my turn."

A quick moment of silence, then, "Did he suck your cock?"

I was shocked by her use of that word. I don't think I'd ever heard her use it before.

I plainly replied, "Yes."

She smiled, "Well, is he better than me?"

I demurred, "Let's just say it felt different."

Again, she smiled, "I bet it did." She then asked, "How?"

I sighed and admitted, "He likes to be forced. So, I, um, basically just, you know."

"No, I don't. What?"

"Used his mouth. Rammed it into him."

"Jesus."

And again, a moment of silence.

She looked at me and quietly asked, "Did you suck his cock?"

I knew what I was about to confess to, I hesitated a brief second, "Yes."

"Oh my God! You sucked another man's cock? I can't believe it. How big is he? Did you make him cum? Did he cum in your mouth? He did, didn't he? Oh my God!". She paused, "Well?"

"His dick is a little larger than my thumb when it's hard. And yes, he came in my..."

I didn't finish the sentence.

Jackie's eyes got wide and her mouth was open. "Did you fuck him?"

"Yes."

"Oh God. Doggie?"

"No, he was leaning against the wall."

She smiled again and almost snickering asked, "Did he fuck you?"

I sharply replied, "No!"

Silence for a moment. "What did you mean, he likes to be forced?"

"He likes to roleplay that he's being forced to do it, that he doesn't want to. That he's a helpless little girl. He likes to pretend he's being raped."

"Fuck."

We rode the last ten minutes in blissful quiet.

We got out of the car and Jackie walked briskly to the front door and rang the bell. A minute passed and Jackie rang the bell as the door opened.

Terry stood there with a stunned expression on his face. He was wearing a white t-shirt, blue jeans, chucks. He didn't have any makeup on, but he looked cute, yet frightened.

Jackie moved right in front of him and he took a few steps backward. She reached out and grabbed his wrist stopping his retreat.

"So, you're fucking around with my husband, are you?"

Terry looked uncertain as to what to say and before he could answer, Jackie moved closer to this beautiful young man, put her arms around him and pressed their bodies together. I knew Jackie was experiencing what I had earlier. His soft subtle body seemingly melting into hers. I also realized that Terry was felling Jackie's firm tits pressing into him.

Jackie rubbed her face on the top of his head, feeling and smelling his silky hair. She bent her head down and they kissed. It was a long passionate kiss.

When they broke, Terry sighed, "I've never been with a woman before, never truly kissed one, except my mom and sister, but never like that."

Jackie smiled. "Well let's change that."

They embraced again and kissed longer this time, each running their hands over each other's backs.

When they stopped. Jackie took a step back, eyed this perfect little sissy up and down, smiled and said, "God you're hot." They both smiled, remembering that is what Terry had said to Jackie when he first saw her.

Terry put out her hand, "Let's go to your bedroom." As they walked away, Jackie turned, looked at me, smiled, "Yes dear, you too. Don't want you to miss out on a thing."

Once in Terry's bedroom, Jackie tore off her suit jacket and reached down and pulled Terry's t-shirt over his head and off. As soon as she had it off him, she leaned in and kissed him passionately again. His arms fells around her. Both embracing tightly. Jackie started to kiss, suck and nibble this boy's neck. His moans sounded like a little girl. In their embrace, it looked as if it was a young girl kissing an older woman.

My cock thickened as I watched. I took off my suit jacket, slipped off my shoes and just stood there watching, wishing it was me, again, kissing and holding that little faggot.

Jackie mouth continued to explore the smooth, soft skin of his shoulders and then his chest. When she started to suck his nipple, his hands went to the back of Jackie's head and pressed her face into his chest. He looked down, watching her suckle him.

"Oh mommy, that feels so good."

His remark caught me completely by surprise. What the fuck was swirling through this sissy's deviant little mind?

Jackie responded by moving her head over and sucking on his other 'tit', with renewed vigor.

His head bent back now, enjoying my wife's manipulations on his chest.

Jackie sank lower, kissing his firm tummy. Making him giggle like a schoolgirl when she tongued his bellybutton.

The giggling stopped when Jackie crouched down. Her knees on either side of Terry's legs. Her business skirt rose up exposing most of her thighs. Her three-inch black heels flat on the floor. Her blonde hair cascading over her shoulders. Through the back of her white blouse, I could make out the outline of her black bra strap.

Jackie was looking up at Jackie. He was staring back at her. She reached up and unbuckled his belt, unbuttoned his jeans and slowly pulled down the zipper.

Terry's breathing became labored. His hands resting, fingers caressing the sides of Jackie's head.

Jackie tugged at his jeans and slipped them over his tight little ass, pulling his white briefs with them.

I smiled, thinking I thought he'd be wearing a pair of his mommy's panties.

Their eyes still locked together, I moved to their side wanting to see Jackie give this young man his first oral by a woman. My wife.

Jackie quickly glanced down to his feet, not allowing herself to see this boys cock. She helped him step out of his pants, undies and then pulled off his socks.

The perfect sissified young man stood completely still now, looking down at my wife.

She raised her head slowly. Her eyes taking in his feet, ankles, skinny calves, knees, his thin hairless thighs and then resting on her prize. His thumb sized stiff dick pointing at her face, poking out from his bald ball sac.

Jackie's hands reached up and each grabbed hold of Terry's tight, small butt cheeks. Her red fingernails, in sharp contrast to his lily-white skin, dug slightly into his ass.

She again looked up into his eyes. Terry and I both watched as Jackie parted her pink painted lips, opened her mouth, leaned forward and took his stiff little cock and his small ball sac entirely into her mouth.

"Oh mommy!" Terry moaned out loud. His hands now pressing against Jackie's head. His eyes closed, his head slightly back. He was on his tiptoes, his legs taking the shape of a young girl.

My own cock responded at the sight. Her cheeks indented as Jackie started to suck on his cock and balls wedged in her mouth. It looked like my wife was sucking on a young teenaged girls' cunt.

I loosened my tie, unbuttoned my shirt and took both off. Next my trousers, t-shirt, underwear. I stood there naked, except for my socks. My cock fully loaded. I went over and sat in the desk chair watching my wife from behind. Crouching in front of this perfect little boy. Her blonde hair cascaded over her shoulders, waving slightly as she was lapping up this young man's cock, savoring it, wantonly try to devour it. My fist gripped my dick and I started to stroke it slowly. I didn't want to cum. I wanted to outlast the erotic scene unfolding in front if me. Instead of this pretty boy, I was envisioning my precious wife, on her knees, sucking on the pussy of a young schoolgirl.

Terry started to moan softly, then louder. I realized he was close to cumming. I wanted to Jackie's face when he did.

I let go of my dick, stood and walked to the side of them. I knelt. Terry had his fingers tangled in Jackie's silky, soft blonde hair, pulling it back away from her face. We both had the perfect view of my wife's face as she was now just sucking on the hardened thumb sized cock of this little boy toy.

Her cheeks indented, her eyes looking up into Terry's big brown eyes. Those eyes focused on watching Jackie, my beautiful wife, lovingly worshiping his cock inserted in her face.

His grip tightened on my wife's head and he grunted. I saw Jackie flinch as the first spasm of his young warm sperm coated the inside of her mouth. Her lips tightened around the base of his dick, not wanting to waste of drop of his jizz. Her throat pulsed, as she swallowed this boy's cum. She was ready for the second wave and I could see her savoring the taste and texture of his salty, musky cum just as I had earlier.

As he continued to cum in shorter spurts, Jackie kept swallowing each one. Not spilling a drop. She was looking straight up at the little bastard. I could smell her own pussy scent waif up from between her thighs.

He let go of her hair and looked down at her and smiled. Terry looked so sweet. Jackie stood and they embraced and kissed deeply.

Jackie smiled, "Undress me." Terry reached up without hesitation and started to unbutton my wife's white blouse. His eyes opened wide when he pushed the blouse open, starring at her black support bra covered "C" cup tits.

Jackie pulled the blouse out of her suit skirt as Terry reached up and unhooked the bra from the front and moved the cups aside. Jackie let her shirt fall off as the little sissy started to fondle my wife's soft, firm tits.

He sighed excitingly, "I've never felt anything like this! You're the first woman I've ever touched!"

His hand groping, squeezing, over and under her tits. She was smiling lovingly down at him.

She let him play as she unzipped her skirt and let it fall to the floor. He pinched her nipples and she winced, "Easy honey. Easy."

He moved his hands away and sheepishly apologized, "I'm sorry."

She moved him to the bed and he laid down looking up at her as she twisted her hips out of her pantyhose and stood naked, letting him look her up and down. Then she climbed onto the bed and they embraced. The legs tangling together. They kissed. They laid in each other's arms as I stood watching.

God! It looked like two women hugging. His skinny legs and arms wrapped around my wife's larger body. My cock responding. I sat back in the desk chair to see what my wife had next in mind.

To be continued.

kparc1212
kparc1212
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