tagTransgender & CrossdressersJill's Secret Ch. 02

Jill's Secret Ch. 02


A few weeks had gone by since our first night together and the revelation that my goddess had a little something extra. Well, a BIG something extra. We awoke that next morning still sticky with her cum and of course both us sporting some serious morning wood. With barely a good morning kiss, we quickly got into a sixty-nine with me on top and sucked each other to our mutual satisfaction. Then after coffee and a shower we had sex. Then lunch, followed by me giving her another blowjob. After that, I went home to rest up for work the next day.

Just before my lunchbreak, I got a phonecall from her begging me to come over. How could I say no? When I got there, she was naked and hard and begging me to blow her again. I started to protest, but the look in her eyes plus my own desire to taste her cum again caused my resolve to evaporate and before I knew it I was on my knees with her delicious girlcock down my throat. She came quickly, filling my stomach with her seed. I left afterwards, with a promise from her that my kindness would be repayed that night. As I pulled into my driveway that evening I got a text from her saying a pizza had just been delivered and for me to come help her eat it. I showered, got dressed and went back to her place. Needless to say, the pizza was cold by the time we actually got to eat it.

It became our routine after that. I would go to her house on my lunchbreak and give her a quick blowjob then go back over after work for a night of olympic level sex. Sometimes, she would come to my office in the afternoon needing another blowjob, and with the door locked, I would take care of her.

One night she apologized for needing me to take care of her all the time, but I told I was happy to do so since I loved doing it to her, loved swallowing her cum and also since there was so much I was saving money by not having to buy lunch. She laughed and said I was depraved, but a small voice in my head wondered if it was possible to be addicted to cum. I certainly felt that way sometimes.

During this time she had made a few comments about wanting to fuck me in the ass. Mostly they were jokes, though the way she got hard when she said it made me realize she really did want it. Then there was time I bent over to pick up my clothes and suddenly felt her cock poking between my cheeks. She laughed and pulled away but I saw her precum actually dripping on the carpet she was so aroused.

So, one night, I decided I would give her what she wanted. I waited for Saturday so we would have all day to play. She got her lunchtime blowjob that Friday but I told her I had things to do that evening and wouldn't be able to come over. I spent the evening playing with a small dildo I had picked up on the way home from work to see what it would be like. It hurt at first but after I got used to it I started to enjoy myself. I knew it would be different with her because she was much bigger, but I found myself eager to try taking her inside me.

I showed up at her house just before lunchtime on Saturday and found her naked as usual. I had found out she was a nudist at home and she liked me to be naked as well. So unless I was just coming over to blow her on my lunch break I would always undress as soon as I got there and that day was no different.

As I kicked away my underwear she pulled me into her arms and kissed me deeply. I returned the kiss and slid my hand between us to stroke her shecock. She moaned into my mouth and backed her hips away so I could stroke her easier.

Teasingly, I released her cock and stepped back from her. She whimpered softly and tried to press herself against me but I moved back again. She quirked an eyebrow at me in mock anger and I laughed and ran to the other side of her couch. With a lusty growl she vaulted over the couch and almost tackled me but I sidestepped her at the last second and she fell to the floor. Quickly I got down behind her and ran my tongue up between her asscheeks which elicited a moan from her then I jumped away. She turned to face me as she stood up and I ran around the couch again. She stared at me, trying to decide what I was up to since up till then I had always been eager to get her in bed. I turned away, stuck out my ass and smacked it, "Catch me if you can baby."

She grinned at the challenge, "What do I get if I do?"

I smacked my ass again and wiggled it tauntingly, "Something we both know you've been wanting for awhile now."

The words were barely out of my mouth when she lunged over the couch a second time and again I managed to dodge her, this time giving her ass a slap. She growled again and came up off the floor both hands raised to grab me but I slipped past her and tweaked her nipple as I went by.

This went on for some time and I was very glad I had kept myself in shape. Each time she tried to grab or tackle me I would manage to get away then smack her ass or breast. Once I quickly slipped a finger in and out of her pussy which was dripping wet at that point. Or I would give her balls a quick squeeze. You get the idea.

Eventually she caught me when I tripped over my own feet and fell over the couch. She was on top of me instantly and began spanking me as I struggled beneath her. I finally gave up and said she won and she collapsed on top of me both of panting and sweating. As we had played our game the scent of her arousal had gotten stronger and stronger and now with her on top of me it was almost overwhelming. I knew it was some kind of pheromone secreted from her balls because they always smelled the strongest and when I went down on her it drove me wild.

Laying under her, that feeling was coming over me and I squirmed around until I was on my back with her sitting on my chest. I slid down till my lips were just under her big smooth balls and when they brushed against me I could feel they were actually moist with whatever they were putting out. I began to rub my face on them wanting to cover myself in her scent. I loved feeling her balls on my face but I loved sucking them even more. Unfortunately, they were too big to both fit in my mouth at the same time but I sucked the left one between my lips and began to swirl my tongue around it. Her cock stood above my face stiff and proud as it drooled precum. She was looking down, watching me suckle her testicle and I winked at her as I switched up and took the right ball in my mouth. She ran her fingers through my hair as I sucked and moaned softly but soon she got up her ball popping loudly from my mouth. She grinned and helped me up from the couch, "Time to claim my prize honey." she purred.

"Be gentle baby, it's my first time." I said blushing a little.

She led me back to her bedroom and had me lay on the bed while she went to the bathroom. When she came back she had me get on all fours. I looked back over my shoulder at her as she placed her hands on my cheeks and rubbed them slowly. I felt myself begin to relax and lay my head on the bed raising my ass even higher for her. She stopped rubbing and I felt her warm wet tongue licking between my cheeks going deeper and deeper until she found my tight little hole. I moaned softly and reached back with both hands to spread myself open for her, giving her better access.

She licked and kissed my asshole soothingly for several minutes before getting back up on her knees and picking up the bottle of lube she had gotten from the bathroom. She poured some on her finger and slid it into me. She twisted her finger in and out of me until she felt me relax a little.

It was difficult to relax completely because I knew what was coming and I knew it would hurt. Despite that, I still wanted her inside me for reasons I couldn't explain, even to myself. Maybe it was because the act was so taboo. Maybe it was because I loved her and wanted to show it by giving her this. Hell, maybe I was secretly gay. For whatever the reason, I wanted this and now I was going to get it.

I felt Denise's finger slide out and looked back to see her lubing up her huge girlcock. She grinned wickedly when she saw me looking, "You ready for this honey?" she asked, teasingly, "Because I know I am."

Before I could answer I felt her press the head of her cock against my hole. She was already oozing precum and when she pressed against me I felt that same tingling as when I blew her. Slowly she pushed into me and started stretching me open. I wasn't wrong about it hurting but it wasn't nearly as bad as I thought it would be. Soon the head popped through my tight ring and I gasped in pain, shutting my eyes tightly. She stopped pushing and trailed her fingers down my back,"Are you ok? We can stop if it hurts too much."

I shook my head, "Just go slow baby. It hurts a little, but I want you inside me." I said, smiling, "Never thought I would say that."

Denise smiled back,"Kinda sexy to hear you say it though. Just relax and tell me when you want me to go deeper."

I nodded and concentrated on relaxing my body for her and soon the pain faded some as I opened up for her. She must have felt it too because she continued to ease into me, inch by lovely inch. My hole stretched tightly around her thick shaft and I felt so full inside as she pushed the last few inches into me until her hips were pressed firmly against my cheeks.

She held still allowing me to get used to feeling her inside me. She stroked my back some more and made soft cooing and shushing sounds, "That's it my love just relax. Mmmmm you feel so good. Like you were made for me. I'm gonna stay just like this until you say you're ready, ok? Just take your time and relax and let yourself open up for me."

Her words and soft tone and gentle caresses did wonders for me and soon the pain was almost completely gone. I could feel her throbbing in my ass. I reached back between my legs and tickled her heavy balls making her smile. I opened my eyes and looked back into hers then nodded. She drew her hips back until only the bulbous head of her cock was inside me then she pushed back in. Then back out again. Moving very slowly, letting me feel all of her as she took my ass for the first time. I could feel her rubbing deliciously against my prostate.

Both of us were moaning as she kept this slow steady pace, her hands gripping my hips. Before long I began to push back against her and she started moving a little faster. Then faster still.

Suddenly she stopped and I saw her pour some more lube on her hand then she reached under me and began stroking my cock as she fucked me. Her balls were slapping mine as she pounded my ass. Grunting and groaning with each thrust, our bodies beaded with sweat. My hole stretched and burning but feeling so wonderfully full.

I could sense a change in Denise as she fucked me and though I couldn't define it at the time, I knew things would be very different between us from this point on. I also felt as though I was changing as well. I was definitely going to need some time to figure this out when I wasn't so....distracted.

Denise pumped her hips faster and harder driving herself deeper into me. My body rocked back and forth with the power of her thrusts. The sound of our bodies slapping together filled the room as did our moans and grunts.

Suddenly my cock pulsed in Denise's hand as I spewed my cum all over the bed under me. I cried out her name as my orgasm shot through my body. I could feel my ass clench hard around her thrusting girlcock with each spurt of cum. I had never cum so hard in my life and I thought I might actually pass out.

My clenching hole must have set her off because just as I was shooting the last of my cum on the blanket I felt her erupt inside me quickly filling me with her large thick load. She pumped her hips furiously as she drained her balls in my ass. I could actually feel my belly begin to swell a bit from being so full of cock and cum.

Unable to hold myself up anymore I collapsed on the bed and Denise came with me her cock still spurting deep in my ass. I don't think she had ever cum so much before. Her body covered mine, both of us drenched in sweat. I could feel the warm seed I was laying in and the even warmer seed that filled me.

Eventually, her orgasm subsided but she still held herself in my ass. I could feel her softening and before long her cock slipped from my ass along with some of her cum. I felt it running down my crack and over my balls coating them before mixing with what I had shot on the bed.

Denise rolled off of me and gathered me in her arms holding me tight. I nuzzled my face between her breasts and sighed contentedly. I could feel her cum running out of my gaping hole and hoped she wouldn't be mad about the mess. Both of us were gasping and panting as we came down from the powerful sexual high we had been on.

As we held each other I could feel my whole body starting to tingle, starting in my belly and radiating out. It was a pleasent sensation and I wondered if it was normal but at the same time I didn't care. I loved this woman with all my heart and nothing else mattered.

After a few minutes, Denise let out a long low purr and said,"I never dreamt anything could be so good. I hope you enjoyed it too, because I want to do that again. And again. And again."

I smiled against her chest, "I may need a little recovery time baby."

Denise giggled, "I didn't mean right this minute goofy. But soon. I didn't hurt you, did I?"

I reached down and squeezed her cum soaked member, "You do realize how big this thing is, don't you?" I said laughing, "It did hurt a little at first and I'm kinda sore back there right now but otherwise I loved it and I want more."

"Good." she said and kissed the top of my head, "How about we get a shower and then I make us some lunch?"

"Sounds good to me, though I may have to eat standing up."

"My poor baby. I have to admit I'm surprised you were able to take my cock like you did. When you first said you were going to let me fuck you, I kinda thought I would start to go in and you would be telling me to stop."

I looked up at her, "I did too. To be honest, the reason I didn't come over last night is because I was practicing with a dildo, trying to get an idea of what I was in for. At first it hurt but then I got used to it so I hoped it would be the same with you. But actually, it didn't hurt a lot more and I got used to it a lot faster. I was very surprised."

"Well, I'm glad you liked it. Not real happy you lied to me though. I would have loved to watch you play with a dildo." Denise said, giving my ass a light smack.

"I wanted to surprise you baby. I know you've wanted this for a long time, but I didn't want to make the offer and then back out because it hurt too bad."

"I can see that. Now come on let's get cleaned up." She said getting out of bed.

As I moved to get up as well, Denise saw the cum that had leaked from my ass. I blushed, opened my mouth to apologize but she placed a finger over my lips and said, "Messy boy. You're gonna have to sleep in the wet spot tonight."

Then she giggled and leaned down to kiss me, "Its fine baby, we'll change the sheets later. I'd say let's do it now but I have a feeling we would just mess them up again, wouldn't we?"

"Without a doubt baby." I said smiling.

We went into the bathroom and got in the shower. Normally, our showers lead to more sex but between both of us being hungry and me still being a bit sore, getting clean and getting food was all that was on our minds. As we showered, Denise encouraged me to relax and let all of her cum out. She even pressed on my stomach to get things flowing and soon I felt her warm cream running down my legs. We washed each other lovingly, taking our time and by the time we were ready to get out the flow of cum from my ass had stopped.

We ate our lunch, then put in a movie to watch and cuddled up on the couch. I had found that anytime we were near each other it was impossible for us to keep our hands to ourselves. We touched and explored each other as we watched the movie. It wasn't long before she was hard again and after awhile she began to make a soft whimpering sound. Knowing what she wanted, I had her sit up and spread her legs. I knelt between them and started to suck her. In the last few weeks I had become an expert at sucking her cock but this time instead of playing with her balls like I normally did, I fingered her pussy intead. She came in record time, rewarding me with a big load of her cum that I eagerly swallowed.

Towards the end of the movie we both dozed off snuggled against each other and didn't wake up till dinner time. We decided to order a pizza since neither of us felt like cooking and we certainly didn't want to have to put on clothes to go out and eat. When the pizza arrived I had to remind her to put on her robe before she answered the door.

As we ate our pizza, Denise began giving me that look that told me she was ready for more sex and lots of it. I was feeling the same way especially since my ass wasn't nearly as sore as it had been. We ate quickly, cleaned up, then practically ran to her bedroom.

We got into bed and began kissing each other feverishly. We were both hard in seconds and we stroked each other as we made out. I slid down and started covering her large breasts in wet sucking kisses then suckled at each nipple. This always drove her wild and she arched heer back pressing her breasts to my face.

After several minutes of sucking and biting her nipples she rolled me on my back and straddled me her ass resting on my cock. She picked up the bottle of lube and I felt myself tighten up thinking she wanted my ass again. She smiled then moved down and drizzled the cool liquid all over my cock, "Since you were so generous to me today, I thought I would repay you in kind." she said.

My heart leapt in excitement! I had never had anal sex before, at least not on the giving end, but it was something I had always wanted to do. Unfortunately, every girl I had ever mentioned it to shut me down immediately.

Denise turned around and lowered her ass onto my face as she stroked my cock. I had eaten her ass many times since we had been together and loved how it felt to tongue her tight little hole. I spread her open with my fingers and ate her ass hungrily, my lips and tongue working their magic as her hand glided up and down my slick shaft. I was nowhere near done eating her when she moved away and began to lower herself on my cock. God she was so tight! I'd never felt anything like it as I went deeper and deeper until she finally had my cock buried inside her. Her eyes were closed and her face was a mask of pure bliss. As she began to ride me I wondered if she had a prostate to go along with her cock and balls. If so, I hoped I could make her cum without touching her cock though I would gladly stroke her if she wanted me to.

Denise eased herself up and down on my cock and I reached up to squeeze and massage her breasts. Her moans got louder and she began to move faster. Her girlcock bounced up and down as she moved and drops of precum spattered on my chest and belly. I rubbed her nipples with circular motions of my thumbs. Denise's head was thrown back and both of us were moaning loudly.

I lost track of how long she had been riding my cock when I felt my balls begin to tighten up, "Oh fuck baby yes I'm gonna cum, don't stop!"

She looked down at me and picked up the pace, her ass slamming down on me over and over. She cried out and I felt her tighten around me as her cock exploded shooting her cum all over me. This was too much for me and I came hard inside her and I could swear my load was as big as hers. Her cock continued to gush out all over me as her ass milked out my cum.

As my body went limp, she got up and once again settled her ass on my face, "Taste yourself." she said, her tone commanding.

I did as she said and lapped up my cum from her ass. It didn't taste nearly as good as hers but I didn't mind it, especially in light of what we had just done. I licked her clean then wiggled my tongue into her loosened asshole. She moaned softly and let me eat her some more then she got up and we spent the next hour snuggling and touching each other.

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