It had been about a month since my first experience with Eric, my next door neighbor. We had met about a dozen times since then for some kind of sex. We were getting comfortable in our boundaries and meetings. I had been shopping online and had slightly increased my clothing, makeup etc. and Eric had offered his shop as a delivery location. He got packages there all the time and his wife never thought about it. I had even bought some more costume jewelry. In the meantime I had lost 5lbs, not a lot but had been able to "clean up a bit" doing hundreds of sit-ups. My nails were clean and neat and I had softened my hands using basic moisturizer numerous times every day. I had been trimming all the hair on my body to shorten and lessen it. I did not have a ton of body hair but by doing this had been able to eliminate most on my torso and all on my upper legs. I had managed to trim my pubes down into a neat but full triangle above my shaved clit and balls. My wife had not commented if she noticed.
It was February 8 and both of us already knew we had plans for the following Saturday night. No married man can get away without having a plan on February 14. Still part of me thought I should do something for this guy who instead of ruining my life had become a bigger part of it. I was driving back from a work meeting when I got texted from Eric.
"Jessica. RU busy Wed noon?"
"No," I replied figuring it was our next get together.
"Can I make you a Valentine's Lunch? I know it's not that day but we both have plans."
"Sure babe. Your house?" I asked.
"OK for me to change there."
I knew the answer was yes. The last thing we wanted were neighbors seeing me dressed walking between houses. Me going over there as a guy would not be noticed.
"Sure. Can't wait."
As I pulled into my driveway my mind went to what I could wear for this day. I selected a red bra, panty and garterbelt set and a newer Red wrap dress I had bought. I put this and other items I would need, makeup, wig, jewelry, shoes stockings, lube and condoms into a laptop bag that served as my "travel bag". I also needed a present for him. I struggled here but the next day went and bought him box of cigars.
On Wednesday morning I started to prepare. After my wife left for work I took a nice bath and cleaned myself. I then painted my nails and toenails. I planned on having a quick shower at Eric's but I moisturized anyway. I pulled on some cotton panties and a cami and then my male clothes. At 11:10 he texted me he was all set and come over anytime. I was ready so I grabbed my bag and walked over.
I opened the door and let myself in. I could hear him in the kitchen.
"Hi Babe!" I yelled
"Hey Jess," he replied.
"I am going right up to shower. Be down in a bit."
"Take your time," he replied as I climbed the stairs and entered the front bedroom.
The master was in the back and like at my house we did not play there. The front room had a nice bed and shared a large bath with a shower/tub combo. I quickly stripped, shaved and got in the shower. I cleaned myself again, washed up and dried off. I rubbed myself down with scented moisturizer and I donned my wig and went right into my makeup routine. I had gotten better with practice. I didn't all of a sudden pass but I didn't look like a clown either. Eric had been supportive of my efforts. As usual I tied a ribbon at the base of my cock. Today it was a nice red one and I did a nice bow. I stepped back into the room and got a surprise. On the bed were flowers, chocolates and a wrapped present. On top was a card.
"For a special girl," it read. Wow. It brought tears to my eyes. Now I am not in "love" with him and he was not with me, but it showed me he thought we were special. I opened the box and was stunned. Inside was a beautiful Valentine's lingerie set, a white bustier with little black polka dots and red trim, matching tiny g-string panty and white stockings. At the bottom was a pair of red peep toe 4" stilettos. This was a hot outfit. I held the bustier up to me in the mirror and it was then that I knew I had to wear it instead of the lingerie I brought.
I dropped my towel, placing the bustier around me, it took a bit of time to do up the 8 hooks. I slipped my arms through the straps and pulled it up to my chest. I bent over and made sure my little tits fit in the cups. The bustier was a 38a. I am a bigger (chest not cup) measurement then that but Eric had known and done well. It stretched and held my tits nice. I love tight lingerie. I sat on the bed and rolled the stockings on my feet and up my legs, adjusting and hooking them to the garters. I loved how my painted toes showed through the stockings and that the red would match the shoes and lingerie. Finally I grabbed the panty. It was really tiny. As the string settled in my crack, I could just get my clit and balls into the front. I was glad I had trimmed up. I stepped into the heels again admiring my toes.
"Dinner is almost ready," Eric called up.
"5 minutes," I replied laughing because it was actually lunch.
I picked up my dress and wrapped it around my body and secured the belt. The hem was at my knee and though I had planned on wearing nude stockings I knew Eric would see the white along with my shoes. I picked up the flowers and chocolates and his cigars and my heels clicked as I descended the stairs.
"Eric, thank you so much. It's too much baby," I said as I entered the room. I set down the gifts on the kitchen island and approached him letting him see me.
"Happy Valentine's Babe," as I did a little turn for him in my dress and then stepped into his arms.
"Happy Valentine's Jessica," he said as he took me in his arms and kissed me deeply our tongues exploring each other.
"I trust it fit?" he asked feeling my lingerie underneath my dress.
"It does and I love it and the shoes."
"I can't wait to see you in it, but let's eat first."
Eric took my hand and led me into the dining room. He had always been a good cook and was often making nice meals even when we were just hanging out. Today was no different. A nice roast was on the table with sides. He helped me into my seat and then lit two candles and turned the lights down. Then he opened a bottle of red wine.
"You know I can't keep those flowers," I joked as he served me a slice of roast and some vegetables.
"I know but I thought you would like them and the chocolates"
I sipped my wine and ate slowly. The meal was great as was the company. We continued to be able to talk like the friends we always had been. As I finished my glass Eric poured us more wine.
"You already have me Eric." I giggled, "No reason to get me drunk."
"Not at all baby. Just looking for us to have a nice meal," He came back with a wink.
This is why our relationship was great. It was a done deal. He knew he was going to get lucky today. I was his girl and acted fem but I had no hang-ups or attitude about it. This meal or "date" was all fun foreplay but in the end he and I both knew his cock would be in me. The whole mood of the day had me quite excited. As we finished the meal, I excused myself to use the powder room. Inside I sat and peed and freshened up. I felt a little naughty, so I pulled off the g-string and balled it in my hand. I returned to my seat and carried on the conversation. As we sipped more wine I slid a heel off under the table and slid my foot up Eric's leg. When I got to his crotch I reached out with my hand and dropped the panty on the table in front of him.
"Don't know," I responded , playing the game.
I nodded yes in response.
"No panties. Not that they covered much babe."
"Should we get more comfortable?" he asked hopefully.
"Please. Let's go upstairs," I said slipping my heel back on.
"Why don't we go into the living room by the fireplace instead?" Eric suggested.
We both stood and walked into the Living Room. Eric grabbed the chocolates and I grabbed his unwrapped present on the way. Entering the room, I felt the warmth of the fireplace. The fire and the late afternoon sun through the drapes, left the room in a soft romantic glow. Eric put the chocolates on the coffee table. I handed him his present.
"Jessica you didn't have to get me anything," as he tore at the paper.
"Yeah right. After all you did and got for me today."
"Wow these are great. Thank you," he said referring to the cigars.
"Now unwrap your other present," I said as I stepped to him and placed his hand on the belt. Eric undid the belt and let the wrap dress fall open. I dropped it off my shoulders and it fell at my feet. I was revealed wearing the bustier and stockings, framed by the light and warmth of the fireplace behind me.
"Wow!" He seemed to say that whenever I was in lingerie.
"It's so nice baby, Thank you." We locked into a deep kiss.
"Now let me thank you," I said dropping to my knees.
I unbuttoned his pants and took out his hardening cock, immediately engulfing it. I wanted it to grow in my mouth. I never tired of having his cock in my mouth. He finished undressing and pulled his cock from my mouth as he turned away.
"Please," I begged wanting his cock.
"Hold on," he laughed grabbing some cushions, "You are insatiable"
"I want daddy's cock!" I had used a new phrase.
"My little slut does huh?"
"Yes right now daddy."
Eric grabbed some cushions from the sofa and we relaxed on the rug in front of the fire. As he lay down I took him back in my mouth and went back to sucking. I was lying with my head on his belly and cockhead in my mouth jerking it. Eric's hands were in my hair. I knew we had time so I took it. My hand left his cock and fondled his balls. I sensed his breathing increase and knew he was getting close. Without my lips leaving him I swung between his legs and began bobbing and jerking in earnest.
"Cummingggggggggggg!" he cried.
His warm load flooded my mouth and I swallowed eagerly and then cleaned his cock completely as it softened. Finally Eric pulled me up to him and we kissed.
"That was great," He said.
"Sure was," I giggled.
Eric slapped my ass and rolled me off him as he stood and walked out. I relaxed by the fire as he returned with the wine and glasses. I opened my chocolates as we drank and cuddled by the fire. I felt so comfortable. As we finished the wine we started to get frisky again. We were kissing and hands roaming all over each other. Mine went back to his cock and I helped it come to life. Eric licked his fingers and worked them slowly into my pussy. His two fingers had me very relaxed and moaning around his cock every time he hit my spot. Finally Eric lay back ready to fuck.
"Need lube," I said
"Condom and lube on the mantle."
I stood and grabbed them totally aware of his eyes on me the whole time. This made me feel so good. I rolled the condom on him and applied a generous amount of lube. Still wearing my heels I squatted over him and he held it at my opening. I slowly lowered myself onto him. I loved how he would look in my eyes as we made our connection.
"Oh gooooooodddddddddddd. That feels incredible," I moaned as I slid down completely. I wasn't "loose" but because we had been spending time together I was able to relax and allow his lubed monster inside me.
Eric held my ass underneath me and helped move me up and down as I got comfortable. He lifted my clit out of the way.
"I love to watch it go inside you."
I bent forward so I could see it to. The sight combined with the feeling was tremendous. I had played with toys forever but having him inside me was so much better. Eric grabbed my head and kissed me deeply again. In this position my legs folded under me so I was on my knees straddling him. His legs came up to I was riding him gently in his "saddle". The heat of the fire was radiating on my side, and its light was casting a seductive glow across the room.
"Ooooohhhhh God!" I cried moving gently on him, wanting to take my time.
As I settled in, Eric's hands were on my body. It was great that he liked talking, touching and kissing me. This was all about sex but he let me roleplay, if you will his girlfriend and today his valentine. For me, it let me play the girl role and I loved being his and being slightly submissive to him. Now his hands were on the top of my thighs, feeling the welt of my stockings and the garters.
"That's my girl, enjoy it," he said.
"Baby, you feel so good inside me," I squeezed myself on his shaft.
"Jess, you're so tight"
We moved like this for quite a while. Just me rocking slowly on him, eyes locked. This was a time to savoir each other. My hands had been on my sides, now covered his on my thighs. I gently guided his hands up to my chest.
"You have great tits Jess," he said as he pulled the cups down, "and great nipples."
"Oh, Oh my, Oh my GOOOOODDDDD," I moaned as he pinched my nipples.
He pulled me forward and I felt a new sensation as he took my left nipple in his mouth kissing and suckling on it. It drove me crazy as he was very gentle, almost nursing. My hands fell to the cushion above his head for support and I began rocking a bit faster on him.
"You like that?" he asked as he released my breast from his mouth.
"Fuck yes!" I replied as he took the right one in my mouth.
His hands went to my ass. I figure he was going to spank me, something I had found that I really enjoy, but now he just grasped each of my cheeks and gently squeezed them.
"You look pretty hot up there" Eric told me as I pulled my nipple from his mouth and I sat back up.
I was still moving on him. His cock was nestled inside me and my movements were more a gyration then an in/out thrust. Eric changed this as he pushed up with his pelvis driving his rod deeper into me.
"FUUUUCCCCKKKKKK! So deep," I wailed as his cock pushed up further then I thought it could.
I felt myself opening up further inside as the head of his cock slipped past the inner resistance. All my movement had stopped as I got used to this new feeling.
"You're so deep in me. So good."
His pole had pushed up into my colon. It took me a minute to get used to this feeling but soon I began moving on him again. His thickness rubbed against my spot with every movement. Meanwhile his large cockhead would slip in and out of my colon causing another great feeling. I could barely speak is felt so good.
"OOOOOOHHHHHH. MMMMMMMMMMM. OOOOOOOHHHHHHH Fuck. Fuck. Fuck. Fuck" I wailed.
Eric said nothing. He had a smile on his face looking right into my eyes. His hands had gone to my tits again. Just rubbing my nipples and I continued rocking.
"I want...I want..."
"God Eric, I want to cum."
"Cum for me baby," he said as his hands went to my hips and he helped pick up the pace.
My hands were back on his chest and I was moving back and forth on him, faster every time. My clit was still limp and flopping with each thrust. His cock was still buried in me pressing on me. I had an urge to pee but I wanted to come so bad I held it and continued rocking on him. Then it happened.
"GOOOOOOODDDDDDDDDDDDDD! FUUUUUUUUUUUUCCCCCCCCCCCCCCCCKKKKKKKKKKKKKKKK! YES. CUUUUUUUUUMMMMMMMMIIIIIIIIIINNNNNNGGGGG!" I wailed as my whole body spasmed on him.
For a good 30 seconds I was oblivious to everything. As I came down and calmed down, I began to catch my breath. I was still in the saddle just squeezing him as I leant forward and kissed him deeply.
"Wow," Eric said "That was amazing."
"Yes it was"
"And you came so much." He said showing me what had come out of me that he had caught in his hand.
I took his hand and brought it to my mouth licking it cleaned. I was in for another surprise as Eric pulled me back to his lips.
"Please share." He said before kissing me again, his tongue pulling cum from my mouth.
"Did you cum?" I asked totally unaware.
"I need to rest," I said.
I carefully straightened and lifted a leg and spun on his pole so I was now in a reverse cowgirl. Still wearing heels I was able to lift up and down a couple times, settling back down so he was fully in me, though not as deep. Eric reached for my hips and then his hands went up to my shoulders and pulled me back to him and rolled me to the side so we were spooning as I faced the fire. He had not left me.
"MMMMMMMMMM" I moaned at this great feeling. The warmth of the fire on my face, and the warmth of his body behind me. I could feel his chest hair on my shoulders and his cock still in me.
Eric brought his one arm around my torso and pulled me close. I looked down my body. Still in the bustier, garters attached to stockings. My red stilettos were still on my feet. Keeping his body still, Eric allowed me to move my hips on his cock. We were just lounging now.
"MMMMM," I let out another satisfying moan.
"Perfect," I said resting my head onto his arm, "I could stay like this all day."
"Me TOO!" Eric said as he thrust forcefully up into me.
It took my breath away again and we started moving in this spooning position. He would thrust into me and I would gently meet his thrusts. I thought to myself, this is what it must feel like to be made love to. Eric's hand drifted from my breasts down to my clit which he rubbed gently as we continued.
"Mmmmm. I love this honey," I said, "Make love to me." I realized what I had said and paused.
"Jessica," he paused.
"What?" I asked nervously.
"I love you Jessica," he floored me.
I turned my neck so I could see his face and our lips met.
"I love you Eric," I said before continuing our kiss.
I looked down my dressed body again. My greatest secret, something that no one had known about a couple weeks before. Now I was spooning with my best friend and now lover. I had been fucked, now I was being made love to. I felt so comfortable in his embrace. His thick cock still in me, my stocking covered legs intertwined with his hairy ones.
Eric's pace had picked up a bit and he was kissing my ears and neck with passion. It was his turn. I wanted him to really be able to take me. I rolled off his cock, figuring I would get on my hands and knees. Looking at the clock on the mantel I realized we had been joined for an hour. My pussy felt empty as I felt the cool air. As I looked back at him I saw his huge pole standing straight up. Suddenly I felt very kinky. I leaned down and put my lips over his head and took his cock into my mouth. As I was doing it, I thought, "This is gross." As I slid down though I was surprised. I was nice and clean, so I tasted the lube and my cleanliness before the rubber of the condom. As I pulled off I looked at Eric with a big smile on my face.
"What the hell was that?" he said.
"Pussy to mouth baby, my pussy tastes great."
"You are so kinky," he replied as he pushed me onto my back.
As he came between my legs, I again saw his hard rubber covered cock. It was hard for me and was once again going to be inside me. Part of me so wanted to pull the condom off and feel him bare in me. To let him cum in me. Before I could act on it though Eric once again pushed into my pussy.
"Yeeeesssssssssssssssssssssssssss," was all that I could get out.
Eric lifted my legs and grabbed the heels of my pumps. Using them to spread my legs wide he stayed on his knees and began pumping into me. Our eyes met and except for our moans of pleasure nothing needed to be said. I brought a hand down to my clit and just rubbed gently. I had already had a great orgasm, now I was just enjoying being made love to.
"Can I see your tits?" Eric asked.
I used both hands to pull my bustier straps off my shoulders and pulled the cups down exposing my nipples. Again, another way I didn't "pass" yet at way he made me feel more fem. Our eyes still locked I pinched my nipples and squeezed them together. Eric smiled down at and continued pumping into me. The heat from the fireplace was still at our side, its light reflected off my stockings and also lit up my lovers face. His pace into me was steadily increasing.