My First Time Pt. 02

Disclaimer: This is part of a continuing series about Jessica, a crossdresser from CT. The stories are fiction but based on events that happened to me. Names, dates, locations etc. have been changed. Events have been embellished. Stories are just for entertainment. Some of the stories will be short and some will be longer as warranted. Please comment. I read them and value input, there is a progression so please be patient.

*****

That evening my wife arrived home late. I had already had dinner but we enjoyed some wine before going to bed. As we sat in bed watching the news, I got a text from Eric. Nothing new there, he and I would text all the time about work, sports anything. The wife paid no attention as I opened his text.

"Jessica. Today was great. I know we are both busy but would very much like to see you tomorrow so we can talk."

I felt a pit in my stomach. What did that mean? Would he spoil my secret? I couldn't avoid him though. I texted back that I had some work to set up in the morning but we could meet for lunch. He responded with his usually "thumb up" emoji. I put my phone down and went to sleep slightly concerned.

I awoke the next morning to another unseasonably warm January Friday. I showered and got dressed like any other day ready to work. My plan was to get jobs sorted and then meet Eric back at our houses at lunchtime. I arrived back a bit early and again had the house to myself. After using the bathroom, I though "what the hell" and stripped down. I pulled out a pair of nude lace top thigh highs and rolled them up my legs, and then I pulled on a red lace thong tucking myself in. Over that, to be safe, I pulled on my boxer briefs and jeans and put my socks and boots on. I had worn panties to work occasionally and even with the male clothes over them it made me feel a bit fem.

My doorbell rang. Eric suggested we head down to the local deli we both liked for lunch. We hopped in his truck and drove off making small talk. We ate a quick lunch and then climbed back into his truck. He had a jobsite just down the road and no one was working today so as he pulled in we had some privacy. He turned to me and began.

"Yesterday was great. I can't stop thinking about you," he said.

"I feel the same way. I was nervous you regretted it."

"No, not at all. I do feel we need to be careful and have a plan," Eric added.

I sighed in relief, "I was worried, now I feel better and I totally agree."

We spent about 15 minutes sitting in his truck laying out some ground rules. We both wanted discretion and to preserve our marriages. This was definitely going to be a FWB thing. We both wanted to be "monogamous" sort of, agreeing to not be with anyone else except our wives. It was understood that I was the "bottom" would dress in some way for our meetings, the level would be determined by time etc. We both agreed that we liked kissing, something that surprised us both. Sometimes it might be a quickie and other times we would have a longer period. I told him that while I of course enjoyed orgasming, I really liked him getting pleasure. I didn't need oral from him or want to fuck him. Intercourse would be safe and we promised to be careful not to scratch, bruise or leave any markings on each other. In the end I think we were both happy.

As the conversation ended Eric was giving me a weird look and said, "I am picturing you as I saw you yesterday." Talking had gotten us both slightly aroused.

"I didn't really think this was going to go this way but...," I began to unbutton my jeans and pulled down my briefs so he could see my panty, "We could play a little."

"I have something for you," Eric said as he reached into the door pocket and pulled out a tube of lipstick. "You wearing lip stick were one of the many things that turned me on," He handed me the tube.

It was a deep red color similar to what I had worn yesterday.

"Give me a minute of privacy?" I asked.

Eric climbed out of the truck. I quickly stripped off my boots, socks, jeans and briefs, leaving me in my button down shirt, thong and thigh highs. I undid the bottom buttons and tied the shirt like a woman wearing her man's shirt would do. I then applied a nice coat of the red to my lips. Eric had a ball cap that I put on and pulled low like women wear. Looking in the mirror I decided it would have to do.

I climbed over the center console into the back seat. Thank god crew cab trucks are so popular. We had a big, full backseat. I was up on my knees on the seat when I opened the door.

"Unbelievable!" He said.

"OK for today?" I wanted reassurance.

"Absolutely!" Eric replied as he sat and pulled me close to him.

We embraced and immediately began kissing. I was so happy Eric wanted to hold me and kiss me. Once again being held by him had me feeling very fem. Time was short today though so I quickly undid his belt and fly and he lifted up to help pull is pants and underwear down.

There it was his cock, my world. Eric had a great cock. I was 8-9" when hard and thick. He had nice heavy veins which gave the shaft a lot of texture. He had been circumcised and the head of his penis had a nice ridge around it.

Both my hands went to him. I began to stroke him with one and fondle his hairy balls with the other. Eric broke our kiss, put his head back and let out a deep moan. I giggled femininely and slid off the seat to the floor between his legs. I was glad I had slid the front seat up, it was tight but I had room. Once again I was looking right at his penis.

I looked up at him, "What do you want me to do?"

"Suck me baby. Please."

I opened my lips and slid them down over the head and onto the shaft, bringing out another deep moan from him and a giggle (with his cock in my mouth) from me. I wanted to get him off so I went right into a rhythmic up and down motion using my lips and one hand on him. Eric began thrusting his hips up meeting my downward motion. He was getting close. His hands had been on my shoulders but now came up to the side of my head. He never really was forceful, I think we were still finding boundaries; he just was helping me keep rhythm. It didn't take much longer.

"Jess, I'm going to cum."

"MMMM, MMMM, MMMM," Was all I could respond.

"Don't swallow," he said as he stopped my head, "CUMMING!"

The first shot hit the back of my throat and I lifted a bit to capture the rest in my mouth. Yesterday I had swallowed it down, not really tasting it. Now it continued to pump into my mouth. His semen was thick, warm and had that salty taste. My mouth was filling up as he finally stopped.

"Show me," he said as I lifted my head up.

I proudly opened my mouth and presented his load on my tongue, my eyes went right to his. I was proud of myself and I could see he was proud as well. I had become his little sissy.

"Swallow!" He commanded.

I closed my mouth and savored the taste before it slid down my throat, before opening and showing him my empty mouth.

"MMMM, God I love your cum."

"You can have it anytime."

It was right there as I returned and cleaned his cock with my tongue that I knew I was going to continue on this path. We talked a bit more as I dressed and wiped the lipstick off and then drove home. We made plans to get together on Monday and I entered my house.

While I showered that evening, I thought about how I could discreetly help my look. I decided to start doing some exercise. My little fat gave me some feminine curves but I thought I could tone up my stomach a bit with some sit-ups and eat a little less. I would make it a point to moisturize my hands and keep my nails neat. While in the shower I trimmed up my pubic hair and eyebrows a bit. I figured I could slowly work on these areas without being too obvious. The big one was makeup. YouTube was my friend here as I watched videos on natural makeup looks. I was determined not to look like a clown.

Monday came all too soon and after watching my wife pull out of the driveway I set about my transformation for our "lunch date". It was definitely different now. I wasn't just dressing for myself anymore. I wanted to impress Eric. I wanted to be sexy for him. I shaved my face close again and the douched and showered. I rubbed moisturizer all over my body again and tied a ribbon around my cock. I sat at the vanity and slowly painted my toe and fingernails a deep red. For all the effort it took I was sad that I would have to remove the polish in just a few hours. While the polish died I started on my makeup. Keeping it light still, I applied foundation and light makeup around my eyes and my red lipstick. As I placed my wig on I was pleased with the result, though I saw room for improvement.

Eric was bringing lunch; I had kept my ladylike promise and asked for a salad. I prepped the guest room, removing the comforter, putting condoms and lube on the nightstand and dimming the lights. Then I returned to get dressed.

My plan was to wear my sexiest clothes. I did not have a big wardrobe but did have a very nice VS black lace teddiette with a thong back, snap crotch and sheer cups. As I slid it up my body and tucked myself I instantly felt fem. I fastened the back bra strap and positioned my little tits in the cups before sitting back down. I rolled on black stockings, admiring my painted toes and stepped into my stilettos. I was glad Eric was taller than me. It would allow me to prance around in heels for him. I checked myself in the mirror and was pleased. Now I took out my little black dress. It was a simple yet elegant as I slipped into it. It fell to just above my knees and had short sleeves and a square neckline.

Just as I checked my makeup the back door bell rung and I went down stairs and let my man in. He looked great in slacks and a button up shirt. I did a little turn for him feeling quite confident.

"Lovely," he said before kissing me, "Lovely."

We sat down and ate, again I was focusing on being more ladylike in how I ate, drank, spoke, listened etc. Eric complimented me a number of times making me even more comfortable. It was surreal. We continue to have conversations like we always had. I would almost forget I was dressed as a female. I quickly cleaned up from lunch while Eric watched me. As I finished he came up behind me and began kissing my neck again. I could feel his hardness against my ass. I turned, wrapped my arms around his neck and kissed him deeply. Now it was my time to lead. I took his hand and led him upstairs, swaying my hips as I went. As we entered the bedroom I spun and sank to my knees unzipping him.

"You can't get enough of that?"

I shook my head no and then took his growing cock into my mouth. I looked up to see Eric was unbuttoning his shirt. I got him fully hard with my mouth and then rose to my feet. As I stepped back he finished removing his shoes, socks and pants.

Eric sat on the bed and watched as I pulled the dress off my body leaving me in the teddy and stockings.

"Wow! You look incredible in that!" He exclaimed.

"Thanks. I don't have a lot of clothes but I think this is my sexiest," I said as I took a band off my wrist and put my hair in a messy pony before I stepped forward between his legs.

"We will have to work on that. You should have anything you need."

His hands immediately were on me, first at my thighs, then up to my ass and then my waist. He pulled me closer, inhaling my scented body and kissing my stomach through the lace. I lifted one leg up onto the bed next to him and his eyes followed his hand as it felt from my ankle, up my calf to my thigh again. Feeling his hands on me was exquisite. He made me feel sexy. I wanted him to be the man, to take me. I wanted to submit to him and receive his cock into me. Eric rubbed my soft clit through the teddy.

"You don't get hard?"

"Sometimes when I am dressing. Usually I am soft or semi when I masturbate. When I am dressed I guess my mind seeks pleasure from somewhere else."

Eric's hands had gone to my bare ass. He was massaging my cheeks and sneaking a finger inside the thong. We both needed it. I walked over to the nightstand and got the lube and a condom. I opened the wrapper and rolled it down his thick shaft. Then I climbed onto the bed brushing past him and positioned myself on my hands and knees in the center. When Eric stood and turned he was looking up my stockinged legs to my shapely ass framed by the garters and thong. I knew I had a nice butt. It had a bit of fat but was firm.

Eric climbed onto the bed and started to pull the thong to the side.

"It's got a snap crotch babe," I directed him.

He reached down and popped the snaps flipping the thong strap onto my back. I reached down and tucked the front up in the front of the teddy. As I did this I felt a cool, lubed finger start to play with my opening. Purring gently I wiggled back trying to get it inside me. Eric took his time working one then two fingers into me stroking my spot. I was relaxed and hung my head down and noticed I was leaking from my clit. I was totally zoned out when he smacked me hard on the ass with his free hand. I almost came right there. I looked over my shoulder at him and smiled.

"I love your butt," He said "Can we do it doggy?"

"MMMMHHHHHHMMMMM," I responded as he withdrew his fingers and coated his cock with lube.

He moved forward and placed his prick at my pussy and began to enter. He was slow but deliberate. Again he eased in and I soon felt his hair touching me. Both his hands went to my hips as he pulled and held me fully on him. Even in this submissive position, and doggy is fully submissive for the bottom, I felt a sense of pride. I was his; I was taking him fully inside me. He wanted to do this with me even though I was "Non-Pass". It wasn't a one-time thing or a mistake.

Eric's slight withdrawal brought me back to reality.

"You good?" He asked.

"Perfect," I swooned.

He pushed back in and I met his thrust squeezing gently. Moans came from both of us as we continued this motion. Eric's hands would leave my hips and roam my back to my shoulders and then down to my hips again. He would slap my ass causing me to go crazy for a second. With every stroke in he hit my spot and I would dribble a bit.

"I love how your ass jiggles every time I bottom out."

"I love how my pussy feels when you bottom out," I replied.

We had been going quite a while when his pace began to quicken. He was grunting with each thrust and I knew he was going to cum soon.

"Want to cum on my face baby?" I asked.

"Fuck yes! So close!" He replied.

As he withdrew I fell forward onto my stomach and quickly rolled over. Eric took in the site of me still in my teddy as he straddled and slid up my body. It was too much for him. As I reached and pulled the condom off he aimed himself and pulsed over my face. His aim was good and his first shot hit from my forehead down my nose to my open mouth. It was so hot being eye to "eye" with his cock and watching that first spurt come right out at me. He followed with 4-5 more moaning spurts of his thick cum before I snared it in my mouth to catch the remainder.

"Jessica yes. That's great," He said as I cleaned up his sensitive cock.

"You're covered," He followed, "I'm sorry."

I had been given a proper facial. Cum was in my eyes, on my forehead cheeks nose. I released his cock and he stepped back and watched as I used my fingers to clean his cum from my face.

"Need a towel?" He asked.

I shook my head NO and then used my fingers to guide the cum into my mouth, swallowing everything I could.

"Holy shit Jess! That is so hot."

"Thanks and thanks for that load," I said smacking my lips, "I love your cum."

Eric pulled me up and kissed me deep and full on the lips. I was surprised and turned on by this as I still had remnants of his load in my mouth. We broke the kiss and Eric lay on his back and I joined him with my head on his chest as we recovered. I hadn't had a big orgasm but felt well fucked and sated.

"Good girl," He said as he held me.

"I want to be your girl."

"You are Jessica. I want you to have whatever you need. Clothes, makeup etc. Is money an issue?"

"No. It's more getting and storing stuff."

"I will help however I can."

"Thank you Eric."

We lay for a bit longer and then Eric got up, dressed and was ready to leave. He gave me another deep kiss, one hand on my right tit and the other squeezing my ass. We said our good byes and then I stripped the bed, and started the laundry. Returning upstairs, I was still in my lingerie. I grabbed a dildo and clit vibe. I lay on the bathroom floor, my pussy was still lubed and the dildo, smaller that Eric slid in nicely. I placed the textured vibe on the underside of my clit head and let it do the work. It didn't take long before I was ready to cum. As I did I moaned one word.

"EEEERRRRRRIIIII IIIIICCCCCCCCC!!"

As I finished I stripped, removed the polish and makeup and climbed in the shower, returning to my male self though eagerly awaiting our next encounter.