My First Time


As the rain pelted down on the roof I sank into the warm water of the bubble bath. I couldn’t believe my luck. I was all alone in the house and now the rain had given me a day off as well. Just as I lay back against the tub my phone beeped a text from my wife. She had met her mom and they were on their way to the city for the day. I stretched out my long legs and relaxed. Today Jessica would be in the office. I am a 35 year old closet CD. I have been dressing for many years and no one knows my secret. Over the years I had amassed a bit of lingerie, some babydolls and nighties, a LBD and a business suit that fit my 6ft 200lbs frame. I had added some makeup, wig, clip on earrings and my one big purchase was a pair of 4″ stilettos.

I had already shaved my face nice and close before getting into the shower. I am generally not hairy and have always trimmed the hair around my “clitty” and shaved down around my “pussy” as I referred to them. I like to be as clean as possible so I had already douched myself twice and was soaking in the tub with the third wash in. As I washed my body I thought about my day. Since it was raining I would not be able to work today. Instead I planned on playing my own secretary and taking care of some of the paperwork that being self-employed would pile up. With my wife not due home until late tonight, I would have time to work, play and clean up. My wife and I have a great relationship and even have great sex, just not enough. I need more so I like to dress and play.

As the water started to cool I hit the drain and turned on the shower. I squatted and emptied myself of the douche seeing that a clear stream came out. I rinsed off and got out of the shower drying myself with a big fluffy towel. I wrapped it around my torso like a women and went into the master. My wife wouldn’t notice my use of a little moisturizer which I spread over my body along with her deodorant so I smelled feminine. I keep my clothes in a trunk in a storage area. The wife never goes there and I had pulled it out before getting in the tub. I selected a white, lace bra, and thong panty and garter belt set. I hooked the bra around my chest and it held my little AA cup titties nicely. I seldom stuff my bra. I have a little breast fat and love to feel them encased in lace. Hooking the garter belt around my waist, I sat on the bed and rolled nude stockings up my legs, hooking them to the garters. I love the feeling of stockings on my legs and garters pulling from my waist. Finally I slid the lace panty up and tucked my little flaccid cock and balls in it as the thong nestled between my cheeks.

I sat at my wife’s vanity and rubbed a bit of foundation on and then applied some lipstick. I placed my wig on and combed the shoulder length hair out. I added some clip on earrings. That was enough for today. I returned to my clothing and pulled out the white blouse and put it on. It was just transparent enough to see my white bra through which made me feel a little naughty. Then I pulled up the pencil skirt so the hem was just above my knee. I tucked in the blouse and fastened the skirt at my waist. The outfit has a jacket but I decided not to wear it today. I stepped into the heels and looked in the mirror. I was pleased with the results. While I could not hide my “manly” hands and face, my dressed body looked womanly. I was no longer Jesse, I was now Jessica.

My heels clicked as I walked to the kitchen for fresh coffee and then to my office and sat at the computer. I smoothed my skirt as I sat and then set about entering bills, generating invoices and returning emails. Occasionally I paused for a sip of coffee and looked out the window, past the covered porch, at the rain still coming down. About an hour had passed and I had gotten a lot of work done. I looked up again and saw Eric looking back at me, and froze. Eric was my neighbor. Also married he was 45 and I guess he would be called a bear. He and I were friends, played golf together, watched sports together etc. I was caught. I was scared but I also knew I had to do something. I couldn’t hide, instead I rose, and as he watched me, walked to the slider and asked him in. As he entered walked to the kitchen and poured him coffee. He followed and sat on a stool.

“So this is me” I said, “I crossdress” Tearing up a bit.

“Jesse” he said, “Its ok”

“No one knows!”

“I won’t tell anyone.”

He then changed the subject and talked about the rain and work and he had come over after seeing my truck in the driveway. We talked for a while and I almost totally forgot I was dressed. Then he returned to the subject.

“Have you been with anyone else since marrying”?

“No, and I have never been with a man” I answered as his hand touched mine. I had never thought of Eric in a sexual way. I would dress and masturbate with a dildo but never thought of being with a man. Now I was.

“Neither have I”, he answered and then he leaned in and kissed me. It was a short kiss, just lips touching, but it changed us. As we broke we looked at each other, stood and embraced again and locked into a deeper, passionate kiss, tongues exploring each other. As my clitty throbbed in my panties, I dropped my hands to his crotch and Pendik Esmer Escort felt his growing member. He moaned into my mouth as I stroked it though his pants. I was so horny at this point I couldn’t stop. Instead I broke our kiss and sank to my knees and began to unzip him.

“Jesse” he stopped me, “you don’t have to do this.”

“It’s Jessica and I want to. Do you want me to stop?”

“God no”

I unzipped him and removed his semi hard cock. It was about 7″ long and protruded from a thick bush of dark brown pubic hair. I inhaled his scent, clean, but clearly male as I stroked him harder, he grew to over 8″, smiling down at me as I looked up in aww. Licking my lips I kissed the tip as I prepared to suck my first cock.

“Nervous” I said.

“Jessica, its ok”

He called me Jessica! I opened my lips and slid them over the head of his cock. I tried to think of how I liked to be sucked. I alternated sucking the head and jerking him with trying to deep throat him. All the time he was moaning. I had no experience here and even though I was trying to act fem I wasn’t sure how I was doing. Suddenly he called my name out again and it was different. His “Jessica” was frantic.

“So close” he followed

I clued in. He was going to cum. Quickly my options flew through my head. Should I just stop, let him cum on me, in me, spit, swallow? I knew this man a long time. I knew he was clean and knew he would keep my secret. Still maybe I should seal the deal. I pulled my lips off.

“Give it to me baby!” as slutty as I could sound before going down on him again.

A couple more pumps and he erupted in me. I had tasted my own cum before but having cum shot into my mouth was different. I felt very submissive and aroused by the act. I was his cocksucker. I knew this wouldn’t be the last time. I swallowed every drop and rose to my feet straightening my skirt as he zipped up.

“Wow” he said

“Yeah Wow” I replied.

We stood silent for a bit sipping coffee again. Emotionally I was lost. He sensed this and sat on his stool inviting me to him. I sat in his lap and he put his arm around me.

“Did you enjoy doing that as much as I enjoyed it?” he asked

“I did” shaking my head, “What does it mean for us?”

“It means that we are closer than we were before. That is if you want to be.”

“I do, but I am scared. This has always been my secret”

“I don’t want you to be scared. I want us to be like we have been, good friends, now we it’s a kinky secret that we share.”

“Want more coffee?” I asked.


I hopped off his lap and walked to the pot.

“You are so feminine in your mannerism, you even walk like a women.”

“Thanks, I have been practicing a while. I like to act as fem as possible when I am dressed” as I returned to his lap with our coffee.

We continued talking. Eric of course had questions, how did my dressing start, etc. I answered him and the conversation was really like it was normally between us, I was just acting fem. His arm remained around me gently stroking my stomach through the silk of my blouse as we sipped our coffee. I related about how I loved dressing and acting fem, though I had never been out in public. I would often dress and masturbate but then would feel ashamed of what I had done. I could tell he had recovered as I could feel him swelling against my ass. He put down his coffee and began kissing my neck. As I moaned gently his free hand went to my crossed legs and he pushed up to the welt of my stocking feeling the bare skin and garter strap.

“Stockings???” he inquired.

“Yup.” You like?”

“Yes” as his lips returned to my neck. “You smell great.”

I turned to face him and we locked in a deep kiss again. As we broke he was hardening in his pants.

“Do you want me to go down on you again?”

“I do but I would like to see and do more with you”

“You want to fuck me? Are you sure? “

Eric gently pushed me off his lap and took my hand. He had been in my house many times. He led me upstairs. As we headed to the master I paused. He looked at me and made the same realization. We couldn’t do it there. Instead I guided him to the guest room. I told him to get comfortable while I freshened up. I headed back to the master where my trunk was. I grabbed some lube, a syringe and went into the bathroom. I pulled my thong down and inserted the syringe and filled myself with the lube. I pulled up my panty, freshened my lipstick and brushed my hair. My heels clicked as I walked back to the bedroom pausing only to grab some condoms out of the trunk.

As I entered the room I saw Eric had been busy. The lights were low, the bed was turned down and on it was my friend, completely naked. Eric wasn’t some perfect hunk. I had never been attracted to him or any man before today. Today I saw him different though. He stood about 6’4″ and weighed about 250. He was a big guy, nice belly, and slightly graying hair. I looked at his broad shoulders and big chest and belly. He had a nice covering of hair there as well as on his legs. I found this very attractive as it made him even more masculine to me, especially when Pendik Eve Gelen Escort I looked to where he was the hairiest and saw what would become the center of my world. His cock emerged from a thick mat of coarse hair. He was sporting a semi so it jutted straight out 7″ from his body nice and thick. Two full balls swung below.

“Hi” was all I could get out.

“You said to get comfortable…”

“I did, are you?” I asked

“I am how about we get you comfortable as well”

He approached me and put his arms around me again and leaned in for a kiss. I could feel his cock jutting into me. As he kissed me he began to unbutton my blouse. I stopped him and told him I wanted to undress for him but I was nervous.

“I can’t be naked” I said, “Dressing, especially the lingerie makes me feel fem”

“Whatever you want Jessica”

As he sat on the end of the bed I unbuttoned the blouse and removed it. I turned my back to him, then I unfastened the skirt and let if fall to the floor. I was left in the bra, panty, garter belt, stocking and heels. I felt his warm hands on my exposed butt and they slid up to my waist as he let out a low groan. Then he gave me a playful but firm slap on my ass, causing me to yelp in surprise.

“You have a great bubble butt. Please turn around.”

“Are you sure?” I asked nervously.


I slowly turned and lowered my head in shame. Eric looked me up and down and made one comment that made me relax. “You are incredibly sexy.” He pulled me to another kiss. I don’t think either one of us had ever considered kissing each other, but now I wanted it so much. I again sank to my knees and took his cock in my mouth. It grew hard and to over 8″. I wanted him really worked up so I was licking, sucking and slobbering all over his thick shaft. I continued to jerk him as I went lower and took each of his hairy balls in my mouth. This drove him crazy; I was then pulled to my feet and laid on my back in the center of the bed. I got a wolf whistle as he looked down at me.

Eric began rubbing my tucked clit through my panties and pulled the thong to the side exposing my pussy. I spread and pulled my legs back as he teased it with his finger.

“Please…” I moaned.


“I want you to finger me”

Over the next 10 minutes he worked one then two fingers into me and he continued to just rub the head of my clit. I was thinking this is the greatest feeling in the world as he stretched my wet pussy open. Finally he withdrew both fingers and I felt empty.

“Ready?” he asked.



“However you want me.” I replied, I couldn’t wait for him to be in me. I expected he would do me doggy, how I had seen online that most guys do CDs.

“I want to look into your eyes the first time” he replied. God he was saying the right things. “Missionary?” I reached for the condoms and handed him one.

“Are you afraid to get pregnant” He joked.

I jabbed his arm “Jerk”.

“I just came in your mouth”

“And I am fine with that and hope you will again but down there is different ok?”

“Its fine Jessica”, as he rolled it down his thick shaft. I added some lube to it, and then returned to the center of the bed on my back and spread my legs. Eric climbed in between them and grabbed my stilettos placing my legs on his shoulders. I looked down at his cock wondering if I could take it inside me. I had played with a lot of dildos but this was the real thing. I couldn’t ponder it for too long as he grabbed his shaft and placed it at my opening, easing it inside. I tried my best to relax but I was tight. He was gentle with me though and looking right into my eyes as he pushed in. He reached down and gently stroked my clit through my panties and before I knew it his pubes we touching me as he bottomed out. He held still and ran his hands up and down my stockinged legs before returning to my clit. I put my hand on his to stop him.

“Eric, you will make me cum.”


“Then I will come down from this high.”

“Ok Jess.”

“Please, Fuck me.” I begged. He slowly began moving in and out with long deliberate strokes. My legs came off his shoulders and with each stroked he pushed at the back of my knees until my legs were bent back to my head and he was above me. He was really pounding me at this point grunting with each thrust.

Every time he bottomed in me I squealed and as he pulled out I shouted for more.


“Fuck me”


“Fuck me”



Sweat was dripping off of Eric’s forehead onto me. I swung my legs out and let him collapse onto my chest and then wrapped them around his waist hooking my heels behind him. Feeling his weight on me was a new sensation. I had never noticed how much taller and bigger he was then me. Now I felt so small compared to him. Eric growled and kissed at my neck and ear as he began moving again. His arms went under my back and his hands gripped my shoulders. As he pulled me deeper onto him, I ended up with my eyes about his shoulder level. I felt even smaller now being taken by this big man. This position caused a new Pendik Evi Olan Escort sensation for me. My clit, still in my panties was now being stimulated by his belly with each thrust. Combined with his cock inside me brought me to the edge.

“Babe” I moaned “I am going to cum”

“Uggghhhhnnnn, me too Jess” thrusting harder.

“Oh god, oh god, oh god. Please don’t stop” I pleaded.

“Cum for me Jess” he said.

Then it happened.

“Cummiiiiiii nnnnnngggggggg!” I groaned as I creamed my panties. Instantly I was ashamed. Normally this is where I would stop, undress and clean up. Now though someone else was participating with me and he wasn’t stopping yet.

Eric kept going but my orgasm had caused me to clench down and he soon was at that point.

“Here I cum baby, oooooohhhhhhhhhhh!” as he filled the condom before slowing down and remaining in me as he collapsed down on me again. I didn’t say a word, he was saying how great it was and how sexy I was but having cum I just felt like I had done wrong. Finally, he eased out of me. I looked down and his softening cock and saw the huge load of cum in the condom as he walked to the bathroom. I sat up in the bed and turned away from the bathroom still ashamed.

Eric came back in to me and sitting on the bed hugged me. He was still nude. At first I flinched at his touch.

“Jessica, its ok”

“I am sorry I came” I cried

He squeezed me tighter. “Jess, why don’t you get cleaned up and come back in here?”

“I don’t know if I can”

“I want you to; we can have some more coffee and watch TV.”

I rose from the bed and walked to the master. I removed my bra and panty and looked in the mirror. I looked at my reflection still in stockings and white garter belt with my clit dangling down. I had to pee which I sat down to do, before wiping up down there. I fixed my hair and lipstick and then looked at my little clit again. I was still ashamed yet now wanted to go back to Eric. I grabbed my white babydoll and slipped it over my head. It was see though with little cups and came down to my ass. I then took a chocker I had, but instead of tying it around my neck I tied it around the base of my clit, hoping to keep it under control. I pulled the matching g-string panty took a deep breath and walked back to Eric, my heels clicking across the wood floor.

“Oh MY!” he exclaimed as I entered the room to find him lying on the bed still nude.

“It’s ok?” as I did a nervous spin for him.

“You are incredible, come here.” He responded as he motioned for me to come lie with him. A fresh cup of coffee sat on the bedside table and Eric was propped up on pillows watching the Golf Channel. I walked to the bed, kicked off my heels and got in lying next to him on the bed. We sat in bed sipping our coffee again and watching the golf. Just like we often did on the couch. Now Eric was naked and I was in a babydoll and stockings. It was about 45 minutes later when Eric ran his hand down my leg again and asked, “Do you always wear stockings?”

“Mmmmm” I moaned at his touch, “Yes baby. Stockings or Thigh Highs. They make me feel sexy also my legs aren’t real hairy but I don’t shave.”

“You have very sexy legs.” He followed, at the same time placing his arm around my shoulders.


Eric pulled me in so I ended up lying with my head on his chest and leg draped over him.

“This is so nice baby” I said, he had me back totally in fem mode. As a bonus I was now looking down his body at his growing prick. I couldn’t believe it.

“Can you go again?” I asked

“Normally no, but you have me so turned on.”

“I have you turned on?” I asked surprised.

My hand slid down and slowly jerked him as he lay on his back. As he hardened, I climbed onto his legs as I jerked him some more. I leaned in for another kiss and he asked if I was ready. It was hard to believe we were going again. I was a bit sore but definitely wanted it. I pulled off my g-string and he saw my little tied clit.

“I love your clit” he said as I blushed.

I grabbed another condom and rolled it down him and added some more lube. I rose up and slid up over his cock and onto his belly. I brought my stocking feet down and was squatting over him. Eric grabbed my waist to steady me. I reached back and lined him up. I had a plan. I wanted this thing in me. Pushing down I felt it start to spread me. I looked right into his eyes and he was looking right at mine. I took a deep breath and I pushed out slightly and lowered myself. He passed both of my rings and slid into me until my bare ass rested in his pubes. The moment of pain was there but was replaced as his cockhead raked my prostrate and filled me completely.

“FUCK” we both moaned in unison before laughing. He pulled and I leaned in for another kiss and I began very minor movements, getting used to it again. I felt like his women. My long hair and earrings dangling in my face, my babydoll was tight around my chest and shoulders and then the sheer satiny fabric fluttered down at my hips and his chest. My stocking covered legs with garters tugging on them all combined with my clit swinging and a thick pole inside me. I sat straight up on him and put my arms over my head making a sexy pose. Eric’s hands left my waist and went to my tits over my babydoll. He gently massaged them. I guess he didn’t mind the light trace of chest hair. Feeling embolden I reached up and pulled the cups down below my nipples.

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