Little Sister Ch. 05

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At a party, Jean goes down on Ralph.
2.2k words
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Part 5 of the 11 part series

Updated 10/01/2022
Created 03/10/2009
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Da_Vida
Da_Vida
172 Followers

When they arrived back at Denise's condo, Denise told Jean to go pick out a dress to wear to the party. As Jean headed to his bedroom, Denise instructed him to pick something sexy but in a subtle way. "Don't choose like a little slut. Show some class."

"Alright, I'll see what I can do," answered Jean.

A bit later Denise came in to check on Jean's progress. She was wearing a black and beige print dress. The dress was open at the neck, had an empire waist and cap sleeves. She was wearing black, closed-toe, Mary-Jane pumps with a T-strap. As Denise walked across the room Jean could hear Denise's dress as it swirled about and against her stocking clad legs. Denise observed that Jean had laid out on the bed a teal, faux wrap dress. The dress had long sleeves and a modest V-neckline. The front of the dress had pleats and there was sash tie. Next to the dress Jean had placed a pair of black satin control briefs, a black and white lace chemise and hose. On the floor was a pair of black, peep-toe platform pumps. "Excellent choices Jean," exclaimed Denise. "Now all we need to do is get you some earrings and a necklace and you'll be a knockout."

At around 7 pm, Denise came in and checked Jean over. She touched up his make-up a little and commented that he was doing very well with his make-up considering how long it had been since he last applied it. She fluffed his curls a little and then said, "We're almost ready to go. Come with me to my room." Denise and Jean went to Denise's room and Denise went in to the bath and came out with a pill and glass of water. She handed the pill to Jean and said, "Here try this."

Jean took the pill and looked at it for a moment and asked, "What is it?"

Denise said, "It is X. Have you ever tried it?"

"No," replied Jean.

"Well, believe me you're going to love this stuff. In about 30 minutes you're going to feel like a girl in love," said Denise smiling broadly.

Jean took the pill and washed it down with the water. Jean followed Denise out of the bedroom and to the front door. Denise opened a closet and took a jacket and handed another to Jean. They then headed for the basement and Denise's car. Denise drove them a short distance to a condo complex in mid-town. They drove up to the front and left the car with a valet. Upon entering the lobby Denise guided Jean to the elevators and it was obvious to Jean that Denise was familiar with the lay out of the lobby. They entered an elevator and Denise punched in a code on the pad by the floor buttons. They exited the elevator at the tenth floor and found themselves in a large open room in which a number of people were gathered, drinking wine and talking. Denise led Jean around and introduced him to a number of the people. Finally, she took Jean over to a handsome man who appeared to be in his late 30s or early 40s. Denise said, "Ralph this is Jean, my little sister, that I've told you about. Jean this is my agent, Ralph."

Ralph looked down at Jean and enclosed one of Jean's hands in both of his and said, "It is in deed a pleasure to finally meet you. You're more beautiful than Denise let on. But, I should have known that anyone as beautiful as Denise would have a beautiful little sister."

Jean blushed and glanced down and away from Ralph's face and said, "You're too kind. I'd like to think that I'm at least not an embarrassment to Denise." Jean looked up into Ralph's face and could feel a warm glow spreading through his body. Jean knew it was probably the drug that Denise had given him but nonetheless felt drawn to and enchanted by Ralph.

Denise looked at Jean and smiled while giving him a quick wink. She then looked at Ralph and said, "Please take care of my little sister for me Ralph. I must go and visit a bit with a few people."

Ralph said, "Of course, I'd love nothing better than to be in charge of looking after a beautiful visitor." Come," he said to Jean while extending his arm to him, "let's go select a wine."

After getting two glasses of wine, Ralph led Jean to a somewhat secluded corner where there was a small couch with its back turned to the bustle of the nearby party. He invited Jean to have a seat and took a seat next to him as he placed the glasses of wine on a small coffee table in front of the couch. Ralph began talking to Jean about Atlanta and asking questions about Denise before she had come to Atlanta. All the while, Ralph held one of Jean's hands in his and gazed steadily into Jean's eyes. He frequently smiled at things Jean said and appeared to be enjoying their quiet conversation. Jean was virtually glowing from his attention and was stimulated by his touch. After a while, Ralph asked, "Would you like to see a great view of the Atlanta skyline?"

"I'd love to," said Jean.

Ralph rose and pulled Jean to his feet. He guided them down a short hallway and through a door, which he closed behind them as they entered the room. The room was only lit by the lights from other buildings entering the room by way of a large window looking out on to the city. The room appeared to be a large office with a seating area to one side that included a couch and two chairs. Ralph led Jean over to the window and they stood arm in arm looking out at the skyline. Ralph noted several points of interest, including the building where several celebrities lived and then turned and looked down at Jean. Jean turned toward him and looked up into his eyes. After a moment, Ralph leaned down and kissed Jean on the lips. Jean felt like an electric charge had run through his body and eagerly returned the kiss. Ralph pulled Jean against him as he kissed Jean's lips, face and neck. Jean felt a wonderful sense of warmth spreading through his body. Ralph began running his hands over Jean's back and then let them slide down to his buttocks. The slippery fabric of the chemise beneath the dress slid over his panties causing Jean to become very aroused. Ralph too had become aroused and Jean could feel Ralph's hard cock pressing into his belly as he rested the side of his face against Ralph's chest.

Ralph whispered in Jean's ear, "I want to make love to you very much."

Jean was very aroused as well and almost answered yes but then snapped back into focus and realized the predicament that he had gotten himself into. Here he was alone with this handsome, aroused man who wanted to make love to what he thought was a beautiful woman. Jean thought for a moment and said, "Ralph, I'd love to feel you in me. You're such a great and virile looking man and I'm really turned on by you, but it is the wrong time of the month."

Ralph said, "What rotten luck I have, but I'm sure you'll be worth the wait. Let's just enjoy cuddling a bit longer."

"Yes, I'd like that very much," whispered Jean.

After a few minutes, Ralph pulled one of Jean's arms from around his waist and guided Jean's hand down to the bulge in his pants. He grasped Jean's wrist and then began to rub the palm of Jean's hand over his hard cock. Jean was almost faint from the stimulation and was breathing heavily. After a few moments, Ralph said, "I'd really like it if you would give me a little relief with a hand job."

Jean could think of no graceful way of extracting himself from the situation and didn't really want to end the encounter on a sour note so he looked up at Ralph, smiled and said, "Yes, I would love to do that for you."

With that said Jean unzipped Ralph's trousers and reached inside for a better feel of the hard cock captured in Ralph's underwear. Jean wanted to feel the hard, hot cock in his hand. Jean unbuckled Ralph's belt and unhooked the front clasp on the trousers. This allowed the trousers to slid down around Ralph's ankles. Jean was now able to more easily get his hand inside of Ralph's cotton knit briefs and wrap it around the throbbing cock. Jean squeezed the cock and felt it pulse in response.

With heaving breath, Ralph said, "Take it out."

Jean responded by beginning to tug on the briefs. Soon Jean knelt on the floor in front of Ralph so that he could get a better angle on pulling the briefs down. As the briefs came down Ralph's rigid cock sprang free nearly striking Jean in the face. Jean reached out and ran his long finger nails along the rigid cock and then took Ralph's ball sac in his cupped hand and gently massaged Ralph's balls. Ralph was clearly becoming more and more aroused. As Jean ran his fingertips along the sides and underside of Ralph's cock, he could see a small bead of pre-cum glistening on the tip of the cock's bulbous head. Jean could not resist the impulse to reach out with his tongue and flick the bead of pre-cum off the head. The feel of the cock's head on his tongue and the taste of the pre-cum were just too much and before he even realized what he was doing, Jean leaned forward and engulfed the cock in his mouth.

Jean grasped the cock near the base with one hand and placed his other hand on Ralph's naked and hairy leg. Jean began running the cock deep into his wide-open mouth until he could feel the soft head pushing against the back of his throat. When the cock head reached the back of his throat, Jean would close his lips around the hard, hot shaft and pull his head back letting the cock slide through his mouth. All the while Jean was caressing the underside of the cock with his tongue. When the cock was almost ready to exit from between Jean's blush red lips, he would open his mouth and take the cock back deep inside his warm wet mouth until he could feel it pressing against the entrance to his throat. A few times on the withdrawal stroke, Ralph's excitement caused his cock to slip from between Jean's lips with a slurping pop. The sound of his cock popping from Jean's mouth seemed to even further excite Ralph. After a number of strokes, Ralph's cock was wet and slick with saliva and pre-cum.

Ralph reached down and gently took Jean's face between his warm hands and tilted Jean's face up so that they could make eye contact. Jean was relaxed, glowing and anxious to be face fucked by Ralph. Ralph began thrusting his cock deep into Jean's mouth, pressing it firmly into his throat, penetrating deeper than Jean had done, then Ralph would pull back about half-way and repeat the stroke. Jean felt completely possessed by Ralph and passively looked into Ralph's glazed over eyes as Ralph continued to fuck him in the mouth. At last, Ralph pressed his cock as deep into Jean's mouth as he could push it and held fast as loads of hot, sticky cum pulsed through his shaft and into Jean's throat. Jean thought for a moment that he would gag on the thick globs of semen but relaxed and it flowed into and coated his throat with a blanket of warmth. Ralph broke eye contact with Jean and leaned back against the wall panting. Ralph's hands continued to cup Jean's face and his still hard cock remained in Jean's mouth. Ralph let go of Jean's face and Jean let the still hard cock slide out of his mouth. He then took the cock in hand and milked it a few times bringing the last of Ralph's considerable load of cum oozing out of the tip. Jean eagerly licked the cock clean and finally released it.

Ralph looked down at Jean's face and locked eyes with him and said, "Jean, that was much better than a hand job and probably the best blow job I've had in recent memory." After a moment, he whispered, "Thank you, thank you. You are going to be a great fuck." Ralph then reached down and took Jean's hands and pulled him to his feet. He looked into Jean's eyes and smiled. He then reached out and wiped a small dribble of white cum from the corner of Jean's mouth with a finger. He then extended the finger to Jean's lips and Jean took the finger gently into his mouth as if it were a small cock and sucked the residual cum from the finger. Ralph leaned down and gave Jean a lingering kiss on the lips. Jean pressed against Ralph as he held him tightly and sighed with contentment. After a moment, Ralph said, "We had better straighten up and get back to the party before people start wondering where we got off to, especially your sister."

To be continued...

Da_Vida
Da_Vida
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AnonymousAnonymousover 10 years ago
Love this story

I especially love it that Ralph is such a gentleman and that he says he wants to "make love" to me. I truly enjoy it when a man fucks me and tells me he is "making love" to me. That makes it feel so perfect being dressed as a woman. Please tell more stories like this one.

AnonymousAnonymousabout 11 years ago
great story

I wish I looked like a real woman when I dress up, so that I can suck a big cock of a man who thinks I'm really a woman. Can't wait to read about Jean getting fucked.

mreneetgmreneetgabout 15 years ago
super series

have enjoyed all the chapters so far!, have left ratings each time!

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