Jerry becomes Jill Pt. 02: Entrapment

This is the second part of my story about how I became Jill. The holidays are over and I return to college and move into my friend Rikki's apartment. She had been a great support while dealing with the death of my parents. Her entrapment of me is stepped up.

I get back to school mid-afternoon on Sunday and get settled into my room at Rikki's apartment. The apartment is large with three bedrooms and two and half baths. I have one of the bedrooms, Rikki one and the other is locked and Rikki says it has personal things in it. Most of Monday is spent getting the my stuff out of my old dorm room. Tuesday school started and we are both busy with school, cheerleading and settling into a routine.

By the end of the second week we had settled into a routine that included me doing a lot of the cooking and laundry and both of us pitching in on Sunday morning cleaning the apartment. I didn't mind all the domestic work as my schedule was a little lighter than Rikki's and I like doing things for her.

That Saturday we had a home basketball game that required us to both cheer. It was an afternoon game, that we won, after which we walked back to the apartment to change out of our uniforms and get cleaned up. As we were walking along Rikki took my hand and asked if I had any plans for the evening.

"No, nothing but maybe watch a movie or read," I replied.

Rikki added, "Neither do I. How about we do dinner together and then have a bottle of wine and watch a or two movie?"

"Great, I said, as we finished the walk to the apartment.

After getting a shower and putting on a pair of sweat pants I go to the kitchen to start working on dinner. I soon realize that if I wanted to do a nice meal I am going to need to run to the grocery store and get a couple of items including a couple of bottles of wine. I slip on a pair of jeans and go by Rikki's room and tell her where I am going.

I am back home in about thirty minutes and when I walk in there is Rikki dressed in a bath robe, high heels and made up beautifully. I look at her and smile as I feel my cock stirring.

"You look stunning," I comment.

Smiling Rikki responds, "Thank you. Let's get dinner going. And by the way I left you an outfit on your bed."

With a questioning look I say, "Thank you" and head to the kitchen to start to work on dinner. First thing is to pour each of us a glass of wine. I give Rikki her glass and tell her to relax and that I will take care of dinner adding, "Rikki, why don't you find a couple of movies for us to watch after dinner?"

It takes me about 30 minutes to get the table set, a salad made and dinner in the oven. I then head into my room to see what Rikki left me to wear. On my bed is a pair of sexy very feminine lacy pink panties and a match camisole. My first thought is I can't wear these, but then remember what happen the last time she gave me a pair of panties. I undress and slip the panties and camisole on and marvel how stimulating they feel and sense my cock getting hard.

I walk through the living room where Rikki is relaxing on my way to the kitchen. Rikki looks up and says, "You look so sexy, Jerry, thank you."

Shortly we set down to dinner and have some small talk about what is coming up in the next week. After dinner I clear the table and Rikki returns to the living room. After cleaning up I go and join Rikki in the living room with two fresh glasses of wine and the bottle.

When I see Rikki I almost drop the wine and glasses. She is has removed the robe and is seated on the sofa. She has her black high heels on along with black seamed stockings, garter belt and a black sheer bra and panty set. Her areoles and nipples are clearly visible through the sheer materials. Her nipples are erect and the scent of sex is in the air.

The sight of Rikki relaxing with her legs slightly spread was enough to get me to a full hard erection. I hand Rikki her glass and sit down on the sofa. Rikki slides over next to me placing a hand on my thigh. I put an arm around her shoulder and she snuggles up next to me and starts the first movie she has picked out.

I don't recall the title of the movie but it about the trials and tribulations of a young man and woman dating. I didn't realize it then but looking back now it is obvious the young woman was in charge making many if not most of the decisions affecting them. While we watch he movie Rikki stokes my thigh and occasionally teases by cock keeping me hard and on the edge. She also nuzzles my neck and kisses me a couple of times.

The first movie ends as we finish the first bottle of wine. After I get a second bottle of wine, Rikki starts the second movie. The theme of the movie is much the same only in this case it is a married couple where the woman is in charge. While the movie is going I put my hand on Rikki's thigh and stroke this lightly, brushing her pussy every so often.

As the movie ends, Rikki gives me a passionate kiss and says, "Remember the last time you asked if there was anything you could do for me and I said no?"

I quickly reply, "Yes, can I do something now?"

"Jerry, I love to orgasm from someone giving me oral sex. Would you be willing to do that for me?" asks Rikki.

"It would be my pleasure," I reply, "but I am not sure how good I will be at it as I have only done it a couple of times."

Rikki smiles and says, "You can learn," as I slide off the couch and on to me knees. I crawl in front of Rikki between her spread legs. Reaching up to her hips with both hands I grasp the waist band of her panties and slowly start to pull these down her nylon encased legs as Rikki raises her hips.

I am now presented with one of the most beautiful sights in the world, Rikki's wet aroused pussy. She has shaved around her pussy lips but left a nice tuff of hair on her mounds. The lips are moist and the smell of her womanhood is intoxicating. Rikki says, "Start with kisses on the inside of my thighs and slowly work your way up to the lips. Kiss then lick these before you start to gently penetrate my pussy with her tongue. The slowly and gently start licking my clit." After this I lightly kiss Rikki's left thigh and begin following her instructions.

Taking my time I slowly moved from her thighs to Rikki's pussy lips before reaching her clit. By the time I lightly licked her clit for the first time Rikki was very wet and moaning loudly. Rikki was starting to move around as I continued to lick her clit. Ricky reaches down and grabs my head and pulls me tight against her pussy and moans "Suck."

I suck her clit into my mouth and lick the tip of this. It only takes a few licks before Rikki explodes into an orgasm bathing my face in her wonder orgasmic juices. After shuddering through her orgasm, she slumps back into the sofa and relaxes.

I crawl out from between her legs and up on the sofa beside Rikki. She leans in and kisses me then says, "Thank you," and then returns to kissing me and licking some of her juices off my face. Rikki reaches down and starts stroking my cock through the panties. After a minute or two she says, "Let's go into my room and take care of your problem."

We break off our embrace and I follow Rikki into her room, with my cock forming a tent in my panties. As we enter the room she asks me to unhook her bra before I go into the bathroom to finish cleaning my face, which I gladly do.

When I come out of her bathroom I find Rikki lying on top of her bed with one hand cupping her left breast and rolling the hard nipple between her thumb and forefinger. Her other hand is lightly stroking her pussy and clit as she quietly moans. She sees me approaching the bed and says, "Strip off your panties and top and lay down beside her.

After stripping off my panties and top I lie down beside Rikki and start stroking my already hard cock. As I get settled in Rikki rolls up on her hand and knees and says, "You can play with your cock, but don't you dare cum until I tell you it is OK. Now keep your mouth closed."

I reply in the affirmative and close my mouth as Rikki lightly rubs first one nipple then the other across the lips of my closed mouth. She slowly raises and lowers her torso while doing this for a while. She then rises up to where the nipple is just touching my lips and says stick out your tongue. I do this and she starts to swing side to side first letting my tongue lick her right breast, then her left, back to the right breast and so forth.

After about ten minutes of this teasing Rikki says, "Open up and nurse," as she lowers he right breast into my mouth. As she does I let go of my cock and reach for her pussy which I find is sopping wet. She pushes my hand away saying, "Don't touch or I will cum, play with your cock and keep yourself close." With this we settle into a pattern of me sucking and nibbling on first one breast and the other while slowly stroking my cock.

After about another ten minutes of breast play Rikki breaks the suction, pulling the breast out of my mouth and turns around on the bed. She pushes my hand away from my cock and says, "Relax and enjoy!" as she lowers her mouth over my cock.

The warmth of her mouth as it slowly engulfs my small cock almost causes me to cum on the spot. Rikki starts to slowly slide her mouth up and done sucking ever so gently on my cock. She senses I am about to cum and releases my cock and allows me to calm down before starting again. Repeating this several times Rikki has me so stimulated that simply blowing on my cock would make me com.

Finally as show lowers her mouth to my cock, "OK give it to me," as my cock slides between her soft warm lips. It only takes a few strokes of her lips up and down my cock before I start shooting a huge load of cum into her mouth.

Once I am done she slips her mouth off my cock sealing her lips and turns and kisses me. As our lips touch Rikki forces her tongue into my mouth which allows the cum to flood into my mouth. With our lips locked in a kiss and our tongues dueling Rikki moans "Swallow," which I do.

As our lips part Rikki says, "I love you."

"I love you too," I reply.

We wrap each other in our arms and fall asleep.

I wake up to Rikki nibble on my ear and neck saying, "Come on sleepy head get up, I have breakfast ready."

I open my eyes to see Rikki dressed in a black lacey lingerie set. I roll out of bed saying, "I'll be with you in a minute, I have to use the toilet first," and head for the bathroom. Rikki follows me into the bathroom, making small talk about the weather and the upcoming week. When I turn around to get something on, she hands me the panties and top from last night, which I take and slip on and head to the kitchen.

Rikki has a wonderful breakfast of fruit, bacon and French toast. As we finish eating she switches from small talk to something more serious. "Jerry I really enjoy having you live with me and our encounters have been very satisfying for me, how about you?"

"Rikki, I enjoy living here, being around you and I am very satisfied as well."

"That is great. I am going to ask you something and I do not want an answer until a week from today. I would like to start dating and let everyone know that we are boyfriend and girlfriend, but there is more to it than that. Are you interested?"

I respond, "Rikki I would love to be your boyfriend, but what else is there?"

"Did you catch the theme in the two movies last night? The theme in both movies involved the relationship, whether dating or married, being led by the female. As you know I am a pretty assertive, take-charge person in most everything I do. If we agree to be become boyfriend-girlfriend it will only be if you agree to let me led the relationship?"

"I think I would like that," I reply.

"OK, then I am going to give you an article a day on female led relationships to read this week and we will discuss them next weekend and decide whether to proceed or not," states Rikki.

"That will be great Rikki," I respond.

To be continued...