Sissy Stepson 10 Stepmother s Sissy
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Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room.
Once in his room with the door locked behind him, he removed the sexy lingerie that the stunning Cassandra have given him from its hiding place. Lance recalled how he washed the sexy garments by hand shortly after he arrived home last week. He then hung them in his room to dry so they would be ready to wear that evening.
That day seemed to drag on until 11:00 PM arrived. He bade his family good night and headed to his room. Once inside his room and locking the door he began to don the sexy lingerie. Locking the door was necessary as detection would have spelled his doom.
His teenage cock twitched as he fastened the silk and lace bra on and inserted the foam stuffing in the cups. Excitement coursed through his body as he placed the garter belt on his hips. He was rock hard by the time he slowly slid the nylons up his legs and was ready to lose his load as he slid the silky panties on.
He then stretched out on his bed and gently ran his fingers over his body. He marveled at the look and the feeling of the silky items under his fingertips. When he reached his cock that was pushing against the silken panties he grasped it. He began to slowly jerk off without bothering to remove them. It didn't take long before he lost his load in the silken cocoon with a small moan.
He eventually slid off his cum soaked panties and used them to clean his shaft off. He slipped under the sheet still his bra, garter belt, and nylons, and before falling asleep Lance recalled the events of last week.
He had gone to the lingerie store to purchase a few items for himself, as borrowing his sister's clothing was becoming too risky. He didn't dare go to the brand new mall, too many of girls from school worked there. He had found this shop by accident and staked it out for over two weeks. Soon he knew the staff on sight. He had waited until Saturday morning when the only employee was an attractive female, her name was Cassandra.
He practiced his story of wanting to buy his girlfriend something sexy over and over, but it was a waste of time. The attractive sales lady had figured out the truth. Cassandra promised him free lingerie if Lance confirmed her suspicions. So he admitted the truth. He was shy about stripping off his clothing, but he complied. As a reward, she removed hers too and assisted him in dressing. They shared some passionate kisses afterward and he was asked to return next Saturday. Before he left they decided on the time.
The clock on his nightstand told him it was now 6:45 AM, so he'd better get moving. He spent a minute or two admiring himself before covering these silky things with his jeans and t-shirt. He then headed out the door and climbed aboard his motorcycle. Fifteen minutes later he parked and chained it behind the specialty shop. He then knocked on the heavy steel door and waited with his heart beginning to beat faster in his chest.
Finally, he heard the door being unbolted from inside. It opened just an inch and Cassandra's lovely face appeared in the opening. She gave him a smile and swung the door open wide and invited him inside. While his eyes adjusted to the dark he heard the door being locked and bolted behind him, less than a minute later she was in his arms with her lips attached to his.
She eventually broke the kiss and took him by the hand and led him to the familiar back of the store. Lance noted that she was clad only in a short thin silk robe and not her work attire. Cassandra saw him clad in his jeans and t-shirt and gave him a pout.
"This will not do. May I?" she asked.
"Please," he responded.
She began to strip off his outerwear to reveal his sexy underwear. Lance recalled how shy he was last week about stripping in front of her, but now he looked forward to it, She embraced him again and the feeling of her sexy silk covered body against his made the kiss they shared even more intense. She ended the kiss and led him to the chairs that she had placed in front of the three-sided mirror
"Now, I am not a makeup artist, it took me years to get my own makeup perfect. But a have few things to help you," she stated.
She then produced a long wig that was the color of his own hair and another article he did not recognize.
"This is a wig cap. It will keep your own hair flat and hold the wig in place," she responded to his puzzled look.
She handed the items to him and gave him instructions on how to wear them. Soon, long and silky brunette hair cascaded from the top of his head to his shoulders. She couldn't believe how the addition of a wig had changed his appearance.
"It looks good on you," she stated.
Cassandra then produced some eye shadow and lipstick, Having watched his sister apply her own makeup on the sly he knew how to apply them. Again Cassandra could not believe how it changed his appearance.
"I have another surprise for you," she informed him.
"What is it?" Lance asked.
"It's in the changing room. Go and put them," she instructed.
Lance headed to the curtained room and went inside. What he saw made his heart skip a beat. There on the hangers were one of the sexiest lingerie combinations that he had ever seen. A long sheer white robe was paired with a sheer white lace bra, panties, a waist cincher and long gloves. There was also a pair of white high heels and nylons with lace tops.
He couldn't remove his current outfit fast enough and don the new lingerie he found. He then placed the heels on his nylon clad feet. He remembering Cassandra's instructions and managed to enter the back room without stumbling. Cassandra was not there so he called out.
"I had to get dressed too," she responded from another changing room.
Less than a minute later she exited her changing room and once again Lance could only stare with his mouth open. Cassandra was dressed in soft black leather pants and top. She looked tough and demanding.
"You look fantastic," was all he could say.
"So do you," she responded approaching him.
"I feel like I'm dressed for a honeymoon," Lance stated running his hands over his outfit.
"Maybe you are," Cassandra responded, taking him in her arms.
They shared a long passion filled kiss before she gently released him. She walked over to one of the long couches where she removed the seat cushions and pulled out the hidden folding bed. It was already made up with a sheet and blanket. She returned and took him by the hand and walked him to the side of the bed.
"So are you ready to lose your cherry?" she asked.
This he did not expect. This attractive older female wanted to have sex with him while he was wearing lingerie.
"Yes, but I don't know what to do," he told her.
"You need to relax and trust me," she said.
Lance sat down on the edge of the bed.
"Keep your knees together, girls do not sit with their legs apart," she informed.
So Lance pushed his knees together putting more pressure on his hard cock and full balls.
"Now we are going to make this more interesting if you're game?" she said in his ear.
"I'm game," he managed to say.
"Good. Now face forward and don't turn around," she instructed.
As Lance sat there, he felt the bed sink and knew that Cassandra was kneeling on the bed behind him. A second later a blindfold made of silk was placed across his eyes. With one of his senses taken away, the others went on high alert.
He felt her hand gently caress his shoulders and slid down his arms.She then moved to his front where she rubbed his neck and chest.The touch of her soft hands through the sheer waist cincher was almost too much.
"You are no longer a teenage boy named Lance. You're a beautiful teenaged girl named Lana," she crooned in his ear.
"Yes," he responded in a feminine voice.
Cassandra got off the bed and moved to the side he was sitting on. She placed her hands on his ankles and swung his legs over, he was now flat on his back.
"Your boyfriend has just dressed you up in order to have sex with you. You will change your mind about giving it to him, but that will not stop him," she continued.
Lance laid there wondering what would happen next. In his mind, he began to mentally change. He had become Lana.
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May-June 1983, Milford, Ohio When we arrived back at the Spencers’ there was a phone message asking me to call Ruth. I was sure what that was about, so I picked up the phone and dialed the number. “Sandy had her baby!” she said. “A girl and she named her Hope.” “Are they both doing OK?” I asked. “Yes. They’re at Clermont County and Sandy wants to see you.” “You realize that if her dad is there, it’ll start World War III? That just doesn’t seem like a good idea.” “He works tomorrow, and...
Characters: Zoe: f, age 14 Noah: m, age 14, Zoe’s stepbrother James: m, age 16, Zoe’s stepbrother Keith: M, age 37; Zoe’s father Kate: F, age 36; Zoe’s stepmother Jessi: F, age 31; Zoe’s mother Jessi was seventeen years old and two months pregnant when she met Keith, my father. A week later during a passionate make-out session, he took her virginity; practically raping her or so she led him to believe. You might wonder how you rape a willing slut that planned and instigated the so-called...
October, 1983, Chicago, Illinois I spent the first three days of the next week thinking about what Bethany had said and anticipating my time with Anala. I was exceedingly happy that I’d asked her to spend some time talking given what Bethany had said to me. Stephie noticed that I was distracted, as did Penny when she came by on Wednesday evening, but I brushed it off as just being preoccupied with class work, my union contracts, and the time I spent running a household. On Thursday morning,...
April 1983, Chicago, Illinois I arrived home just before 8:00pm to find Stephie and Elyse sitting on the couch watching TV. Stephie jumped up and hugged me and gave me a quick kiss. Elyse got up more slowly, and hugged me once Stephie had released me. I poured myself a cup of tea and sat down with the girls to show them the drawing of the basement that my dad had given me. “That sauna is huge!” Elyse said. “It has to fit all of us. Roughly I’d say you could put eighteen people in there,...
Service Girl Stephie #2Coffee house meetingOpen shirt gawking DownblouseSwinging with FriendsStephie, Bobbie & DanParty Lap Dancing and fondlingStage Bondage & Toy’sBobbie hangs around-Literally!Stephie (small tit's) Revealed, Poked and taken past the end (small tit Torture My Favorite!) I met with Stephie to confirm her participation in the party and without hesitation I get a yes, over her coffee drink she tells me about the excitement in contributing to the quality of the party...
April 22, 1983, Chicago, Illinois “So, what’s the plan for tonight?” I asked the girls. “Take a shower and put on some nice clothes. We’re going to meet Dave and Julia,” Elyse said. “Where?” “At the Sig Ep house.” I went to the shower and just as I was getting out, Elyse opened the door. She smiled, blew me a kiss, and said I had a phone call. I brazenly walked past her without bothering to pick up a towel, and picked up the extension in my room. I turned to face Elyse who was standing...
July, 1983, Dawsonville, Georgia Other than being long, the drive through Indiana, Kentucky, Tennessee, and Northern Georgia was uneventful. I stopped for gas three times and food twice, and pulled into Stephie’s driveway in Dawsonville at 9:10pm. She was sitting on the porch swing and got up to greet me as my car rolled to a stop. I quickly hopped out and took her in my arms and we exchanged a passionate kiss. “Hey, Peaches,” I said. “Hey, Yankee,” she answered. “What’s bugging you?” I...
May, 1983, Chicago, Illinois The party had finally ended about 10:00pm, though a few people had left earlier, including Jeremiah. Kurt, Kathy, Dave, and Julia all stayed to help clean up, as did the girls who were staying with us - Katy, Cindi, and Jackie. Elyse and I made several passes through the house to make sure that nothing was left, and Stephie, Julia, and Dave swept the floors and wiped up a few spills. Overall, it wasn’t a lot of work. We folded up the tables and Dave and I...