Finding Himself in Her Ch. 03

Jaime walked into the bedroom and gasped in surprise. The bedroom was romantically lit with candles and lying on the bed was Kara, naked except for a glistening strap-on jutting from her crotch.

"Wow! You look beautiful sweetie! Where did that come from?" asked Kara.

"Thanks, I bought it at the store while I got the purse. Are you going to do what I think with that?" Jaime's voice was tinged with the fear and excitement she felt at the sight of the strap-on. It was about the same length as her own cock but thinner, with a tapered head and fake veins and ridges running down it's clear red length.

"Yeah, I figured that since you like being a woman so much you should feel what it's like to make love like a woman. Now, come here and kiss me!"

Jaime got up on the bed on all fours and crawled up towards Kara. She tried to make her crawl as seductive as possible and rolled her hips and arched her back to display her new breasts and her perky, round ass. She kissed her way up Kara's arm with soft, feathery kisses and then along her clavicle to her neck where her kisses made Kara shudder. Finally their lips met and they started kissing slowly as Jaime straddled Kara, her cock resting between their bellies as the strap-on rested between Jaime's ass cheeks. As their tongues started exploring each other's mouths Jaime felt Kara's strong hands explore her body. They ran along her bare thighs, caressing and squeezing before uncovering and massaging her ass. After a long while the hands continued their journey upwards to her breasts.

The breast forms felt amazing! It was almost impossible for Kara to tell that they were fake, especially with how Jaime moaned and squealed into her mouth as she pinched and pulled on the big, stiff nipples. Kara rolled over so she was on top and kissed her way along Jaime's jawbone to her left ear. She sucked and licked the ear and then kissed and licked down Jaime's neck to her clavicle and further down. Kara pulled the small brunette's slip below her tits and took one of her big pink nipples in her mouth. The slight taste of latex interrupted the fantasy momentarily but Jaime's sexy, feminine voice as she gasped and moaned more than made up for it. Kara kissed her way down Jaime's flat, satin clad belly to her thick cock. She teased the head with with her tongue before licking and kissing her way down the shaft to her hairless balls. She sucked one and then the other into her mouth and when the second one left her soft lips with a slurp she told Jaime, "Pull your knees up to your shoulders sweetie, I want to get you ready for me."

Jaime pulled her legs up and Kara folded a pillow in half under his raised hips. Jaime looked down at Kara as her mouth descended towards her ass and Jaime gasped as Kara's lips kissed her right over the opening. Kara started to work at getting Jaime's ass to relax and to Jaime it felt incredible. She loved the softness of Kara's tongue and pushed out to make herself relax and allow Kara inside. Suddenly the tongue popped trough and wiggled it's way inside as Kara sealed her lips around Jaime's rim and sucked. This felt incredible and Jaime moaned and gasped very much like the girl she felt like.

Kara loved how responsive Jaime's pucker was and felt like she could rim it all night long. She felt the strap-on drag on the bed below her and remembered that she was eating Jaime's ass to loosen it up for bigger things. She pulled her face away and heard Jaime's disappointed moan. She picked up a tube of lubrication gel and squirted some on her index finger and spread it over Jaime's asshole.

Jaime gasped i surprise at the cold sensation and then moaned as Kara pushed her finger slowly inside. She was really starting to enjoy the feeling of being penetrated back there and eagerly pushed back as Kara rotated her finger inside to spread the lube. Jaime felt the finger leave her butt and something hard and slender push inside. Suddenly cold liquid flooded her ass, making Jaime squeal and shudder. She wanted to leave her position but the need to not disappoint Kara was stronger and Jaime just clutched her legs tighter to her shoulders. The strange cold sensation soon gave way to pleasure as Kara's long, slender finger returned to her ass. The finger moved in and out in long strokes that slowly built speed. A second finger joined and Jaime groaned at the thicker intrusion but the slight discomfort soon gave way to pleasure and Jaime started moving her hips in response.

Kara kissed her way up Jaime's satin covered body as her fingers continued plunging in and out of Jaime's loosening butt. She used her free hand to uncover Jamie's breast forms and placed her lips around her stiff nipple and bit down and pulled gently. Jaime gasped into her ear and grabbed hold of her head to keep her there. Kara kissed her way back and forth between the nipples to bite and pull at the fake nubs, making Jaime moan loudly as her real nipples were pinched and pulled by the clamps. Kara kissed her way up Jaime's soft skin to her neck and then to her mouth as her fingers continued their strokes in and out of Jaime's ass. After a searing kiss Kara sat back on her haunches and placed Jaime's ankles on her shoulders and said, "Okay, sweetie, I'm going to take your second virginity now. I promise I'll take it slow and make it as comfortable as possible for you but you have to promise in return to keep your hands away from this." Kara gave Jaime's cock a quick squeeze and continued, "Tonight is all about your femininity and penetration is a big part of that. Just play with your pretty tits and enjoy the ride!"

"I promise. That thing looks kinda big and scary but your fingers feel, OHH, so damn good I can hardly wait for something bigger! Everything I've done with you has been a bit scary at first but it has been the best experience of my life." Kara smiled down at her and a tear ran down her cheek. Jaime felt the fingers removed from her butt and something thicker, harder pushing against her opening. She remembered to push out and suddenly the head of the dildo popped in. Jaime moaned at the twinge of pain and the slightly uncomfortable full feeling, but there was pleasure there as well. Kara kept still for a while as Jaime got used to the intrusion and then started pushing forward. Jaime played with her nipples to help distract herself as her ass was filled more and more. It was a strange feeling to be taken like this, but when Kara started making small thrusts the strangeness was slowly replaced with pleasure. After a minute Kara was all the way inside and rested her upper thighs against Jaime's soft butt as her ass slowly relaxed around the slick red dildo.

Kara took Jaime's petite foot from her shoulder and kissed along it's side as she slowly pulled the strap-on outwards. The head of the dildo caught on the ring of muscles and Kara pushed inwards again as she took the big toe in her mouth to suck and lick. Kara watched Jaime's face as the expressions played over it, pain, confusion, pleasure, joy and surprise at first, then only pleasure, joy and devotion and love as their eyes met and Kara's fake cock pushed in and out again and again, slowly building speed. With every inwards thrust the back of the strap-on rubbed across her clit and with every pull outwards it massaged her g-spot with the curved inwards dildo seated deep in her pussy. Kara let her eyes wander down Jaime's tight little body, first to her perky breasts where her hands slowly worked her nipples and then on downwards over her flat, satin clad stomach and slim waist to finally land on the dildo plunging in and out faster and faster. For Kara it was one of the most erotic visuals, to see a dildo sliding in and out of a beautiful ass, every thrust buckling the rim inwards and every pull out making the rim stand out in it's pretty pink color.

"Do you like the way I'm making love to you sweetie? If it starts to burn I want you to tell me and I'll ad some more lube." Kara asked as her thrusting picked up speed and she added a roll to her hips.

"I love this! Oh God! You're hitting my prostate, MMMHH! Please take me harder. God, I love you so mMMmuch!" Jaime started moaning with each thrust and wanted to thrust back with her hips but in her position, propped up on pillows with her ankles on Kara's shoulders, she could do little more than lay back and take it. Jaime felt like she was on the verge of cumming with every thrust but her cock just jerked spasmodically and a steady flow of pre-cum ran down in a pool on her lower stomach. Jaime played more and more roughly with her nipples to take her mind of the mounting but never cresting pleasure. After several minutes of ecstatic torture Jaime almost felt like she was loosing her mind but just then Kara's moans became louder and louder as her thrusts became harder and more erratic. She grabbed hold of Jaime's cock and jerked quickly up and down and as Jaime's ass clamped down in orgasm the added friction pushed Kara over the edge as well. The two beautiful but oh so different girls screamed out each others names as they came hard. Jaime had never felt anything like this, she just came and came as her butt milked the dildo in her ass. Her balls almost hurt as they shot load after load onto her new satin slip, up over her new tits and all the way up to her face.

Kara leaned down and licked up some pearly cum before planting a sloppy kiss on Jaime's panting mouth. She kissed her way to Jaime's ear and whispered "Now you're a woman, baby." Jaime moaned something unintelligible and Kara kissed her way down Jaime's body, drinking her cum as she slowly pulled the dildo out of her ass. After Kara swallowed the last of Jaime's cum and sucked her dick clean she stood back and looked over her young lover and felt herself grow wet again.

Jaime was laying blissed out and unaware of the outside world when she felt Kara's hands remove her slip, move her body onto her hands and knees and then something was slipped around her wrists. She felt more lube being squirted into her butt and something pushing against her stretched asshole. She moaned out, "Please, it's too soon. OH, OH, OHHHH JESUS CHRIST THAT'S BIG!" It felt like a tree trunk was making it's way inside her ass and it hurt like hell and felt incredibly good at the same time. When Jaime tried to move her hands to escape she realised they were tied to the headboard and there was no escape from the enormous dildo burying deeper and deeper inside her ass.

"You know what it's like to be made love to like a woman and now you are going to find out what it's like to get FUCKED!" Kara said this in her dominant voice but continued in a soft gentle tone as she held still in Jaime's spasming ass, "If something feels wrong or it gets too much, say blueberry and I'll stop immediately, that's our safeword. I won't stop if you shake your head or cry or say stop for that matter, do you understand, sweetie?"

Jaime nodded and put her head down. It hurt a lot but there was pleasure there as well and she focused on that and on pushing out to make the entrance easier for the huge intruder. The big head suddenly rubbed against her prostate and to her surprise a huge jolt of pleasure shot through her body and her cock got hard as steel once again. Jaime arched her back and rolled her hips to get as much pleasure as possible.

Kara loved fucking girls from behind with her huge strap-on, it was ten inches long and slightly thicker than Jaime's sizable cock, and with veins and ridges to add sensation. Kara pushed inwards until it became difficult and then she started pounding deeper and deeper with short, hard thrusts until all ten inches were buried deep inside and her hips rested against Jaime's undulating bubble butt. Kara grabbed a firm hold of Jaime's slender waist and pulled out all but the head before pushing it all the way home. After a minute or so of long strokes Jaime stopped grunting and started moaning as she started moving her body back into the thrusts. Kara took this as a sign to increase her pace and was soon fucking Jaime with wild abandon. She felt an orgasm coming closer and closer and rolled her hips to really work her g-spot. As she came hard she buried the fake cock deep and mashed her big tits against Jaime's back.

When the spasms stopped she pulled the dildo out of Jaime. She loved seeing a gaping asshole and used her thumbs to open it even more before pushing her tongue deep inside. After a while she dragged her tongue out and squirted a big wad of lube into the gaping hole and added a new coating to the big black dildo. She used the last of the lube to make Jaime's perfect ass glisten in the candle light and then she pushed the dildo home hard. This time there was no warm up, Kara just started pounding Jaime hard with long, fast strokes. Kara started spanking Jaime's upthrust butt, loving the way the soft and supple flesh jiggled.

Jaime was lost in a world of pleasure and pain, she desperately wanted to reach down to play with her neglected cock or at least pull on her nipples, just something to push her over the edge. Then the spanks started raining down and the radiating heat slowly pushed her to an orgasm that dwarfed all others. She screamed so hard no sound came out and her entire body started shaking as her ass was filled again and again. The huge dildo milked her prostate and the nerve endings around her butt hole was burning with pleasure.

Kara came with Jaime and laid down on top of her. they both fell to the side and laid there gasping as the pleasure slowly ebbed. Kara untied Jaime's hands and gently eased the dildo out as she planted soft kisses on her lover's neck. She got out of bed and unbuckled her strap-on before going to the bathroom to get a wet towel. She gently cleaned Jaime of cum and lube and removed the top cover from the bed before getting in beside Jaime under the covers. She kissed her forehead and looked at her pretty face. To Kara's surprise Jaime looked back at her with her immensely green eyes and smiled contentedly. Kara said, "I hope you know that I did what I did because I love you and I wanted to give you as much pleasure as possible, and I know you get off on being submissive just as I get off on being dominant."

"It was a bit scary but it is so exciting and freeing to let go and surrender control, I never knew and I would never have discovered it on my own, so thank you for that, and for everything else you've helped me discover about myself."

"You're welcome, sweetie. It's so exciting to shape you into my dream lover and find that you find yourself in that person."

"Yeah, it's so strange and exciting to turn into a girl. It feels so right though, I've felt more alive since I met you, and especially since I got dressed up, than ever before in my life. I think I want to live like this, like a girl, with you."

Kara smiled and a tear rolled down her cheek. She kissed Jaime gently and with love and answered, "I'm so happy for you! But, that is a huge decision to make and with all those endorphins and all that adrenaline rushing trough your system right now you are in no state to make that decision."

"Okay, I'll wait. Will you still love me if I decide against it?"

"Of course I will. Now, lets sleep and we'll go shopping for clothes tomorrow."

Jaime nodded and they shared a final kiss before drifting off to sleep. Jaime's dreams were filled of scenes from her past, only with her as a pretty girl instead of a lonely boy. Bad memories turned happy as the alter ego was treated differently, could stand up for herself, was desired.