After my little s****r, Cassie, put me to bed, turned off the light and left my room, I pushed down the covers and thought about what she'd done with me. My heart was still beating fast, and I pulled the panties she gave me up to my face, rubbed the silky material against my cheek and pressed the crotch against my nose searching for her familiar feminine smell. When I found it, my cock started to harden again and I instinctively reached down to grab my hardening member.
But, remembering my promise to Cassie that I wouldn't masturbate during the night, I pulled my hand back and closed my eyes tightly as I lie alone in the darkness and solitude of my c***dhood bedroom. Being back home and sl**ping in my old bed felt strange, especially under the current circumstances. Having been kicked out of our apartment by my wife when she caught me sitting at the computer, writing nasty stories dressed in those girly panties really wasn't a reason to celebrate my homecoming.
I wondered what she was doing now – my wife, Beth, I mean. Was she jumping for joy, anticipating an opportunity to end our marriage? Or, was she lying in bed, crying her eyes out because she missed her husband? Maybe, she was sitting at the computer scanning the flash drive she took from me - reading my stories, looking at the pictures and discovering all my secret desires. Whatever she was doing, I hoped she'd check the voice mail on her cell phone and listen to the message I left her, begging her to let me come home.
After a while, I finally decided it was hopeless to concentrate on what Beth was going to do. What ever was going to happen, was going to happen. She would decide where to go from here, and I wouldn't hold it against her or fight her if she wanted to call it quits.
Yes, I loved Beth, but, I knew in my heart I betrayed her on so many different levels. I lusted after my secret desires in the way I should have lusted after her.... my wife. I never cheated on her - I never had an affair or did anything online. But, I was addicted to writing those erotic stories because they were my only real opportunity to live the life I wanted to live, and even though it was only on paper, it was all I had.
Those pictures on the flash drive........ well, that was a different story altogether. I took them one day when Beth left early in the morning for work and I knew she wouldn't be home until late. I went through all her lingerie and picked out the pieces I liked, and laid it all out on the bed in our room. At first, I was just going to put everything on, one item at a time, to see which things turned me on the most, But, in a moment of weakness, I found myself setting up the camera and using the self timer feature to take pictures of me in the silky things I liked the best.
Unfortunately, it turned into a full fledged hard-on and masturbation session, and I stupidly kept taking pictures. Then, instead of deleting them, I put them in a folder on that flash drive with my stories and simply left them there. I'm not sure why I didn't delete them, but believe me, I sure wish I had.
In total, there were probably fifty pictures of me in bras and panties, many with an obvious erection and quite a few with me stroking myself. I knew when she found the pictures she'd probably be sickened by them, and that in itself might seal my fate and be enough to convince her to end our marriage.
So, after chastising myself and emotionally coming to grips with the fact that my marriage was undoubtedly over, I tucked my little s****r's panties under the pillow and rolled over toward the wall and drifted off to sl**p.
I woke up around six the next morning with the brilliant idea I'd get in my car and drive home and make a surprise breakfast in bed for Beth. But, I decided against doing that once I realized she might still be seething mad at me and she might not want me anywhere close to her. So, accepting my fate to let time run its course, I got out of bed and snuck into the hall bathroom to pee.
Standing there in front of the toilet, I looked at my reflection in the vanity mirror and recalled the previous night with my little s****r. I looked silly, standing there in her silky panties and her stretched out purple nightie. But, I didn't care. In fact, for some insane reason, I felt proud to be wearing her clothes – it felt like I'd finally achieved something...... finally realized one of my dreams, and for once, I'd spent a whole night as me, the way I wanted to be.
But it wasn't just the fact that Cassie let me wear her nightie and her panties. The events of last night were, without a doubt, the single most erotic, and sexually fulfilling chain of experiences in my whole life. The things she did to me where the things my dreams and stories were made of. It was the perfect mix of submission, dominance and exhibitionism. And, during the whole thing, Cassie was nothing less than gracious and tender with me. She was unbelievably gentle in her manner and in the way she spoke to me, but, she was firm in the way she took control and led me exactly to where I wanted to be.
It was embarrassing, sure. But, as she stripped me and made me masturbate in front of her, a feeling of complete exuberance and inner joy filled my entire soul as she did something no one has ever done for me – she brought my dreams to life.
And while my little s****r was doing these things, I abandoned every other reaction to embrace what she was doing. So now, having had the chance to actually experience a taste of my desires, I wasn't sure if I was willing to go back to my clandestine persona where I lived my dreams solely in my writing.
Time would end up being my master in all of this, I finally resigned myself to believe. Beth would definitely read my stories and look at my pictures, and then she'd make a decision on what she wanted to do. If she took me back, I don't know how we'd be able to exist as a couple without some capitulation and acceptance of my needs. I didn't want to lose her, but, I could no longer live my life in secret.
I finished in the bathroom and snuck back to my room and climbed back in bed. Since it was still early on that Sunday morning, I drifted back to a gentle sl**p and didn't wake up until some time later. When I opened my eyes, though, I was startled to see my mother sitting in a chair by the side of the bed, watching me sl**p.
She was in her robe, sitting there quietly and sipping a cup of coffee. The door was closed and when I looked up at her, she smiled sweetly and said, "Good morning."
I pulled the sheets up to my neck, trying to hide the fact I was wearing my little s****r's nightie, but, apparently, my mother had been in my bedroom for a while and already seen me wearing it as I slept.
"Did your s****r give you this to sl**p in last night?" Mother asked, softly, as she leaned forward and pulled the sheet several inches down my chest.
"Yes," I answered, blushing, "she did."
"I'm a little surprised." Mom replied. "She was hopping mad at you when we were at your apartment talking with Beth. And when we came home, I had to make her promise she wouldn't attack you with a knife before I let her get out of the car."
"We had a long talk last night before I went to bed." I explained. "And, I told her I was sorry for everything I did to you and her."
"That was nice of you." Mom replied. "And it looks like she probably accepted your apology." Mom said, pointing down to the nightie I was wearing.
Then, after a few moments, Mom went on to tell me stayed up a while last night reading more of my writing. "You're a fine writer, Tom." She said. "Many of your stories are told with such realism, and the pictures you paint with your words are vivid and they have dramatic texture. A few of them really made me stop and think about things"
"I'm surprised to hear you say that." I answered. "I wouldn't have expected any of you to compliment me on my writing. Which stories did you read?"
Mother smiled and her face turned red. "Never mind about that." She said nervously. "What I meant is that you have a flair for writing. Maybe it's something you should consider as an occupation, that's all."
"And Tom," Mother added, "I've been thinking about all this...... about you and Beth, your s****r and me, the panties...... and all the stories."
Mom went on to say she read one of my stories that was dated years ago, while I was still living at home...... while I was a senior in high school.
"I never realized you wished you were a girl, Tom." She said, softly. "A mother should have picked up on something like that, and I'm sorry I didn't."
"All those years - you were jealous of your s****r and me." She added. "You were envious of us because we were girls, and you weren't."
"Last night," Mom continued, "I read what you wrote about how you used to love climbing into bed with me in the morning and cuddling up against me when it was cold in the house – back when you were really young. I used to wear those full length nightgowns that were so soft and silky, and, I'd hold you until you warmed up and then you'd fall back asl**p."
"Do you remember sitting on the bathroom counter, watching me while I fixed my hair and did my makeup?" Mom asked. "Or how I used to put clear fingernail polish on your nails?"
"Tom," she said, pausing until I looked up at her, "you always liked girl things....... you liked anything that was silky or frilly or soft, and as I read that story last night, I felt like I'd failed you for not recognizing what you needed."
"You didn't fail me, Mom." I said. "And it's not entirely the case that I wanted to be a girl."
"Not entirely?" My mother said. "What does that mean?"
"It's complicated and embarrassing, Mom." I replied.
"It's too complicated to talk to your own mother about?" She asked. "And too embarrassing? More embarrassing than those pictures I saw last night?"
My eyes shot open. "You saw the pictures?" I asked, horrified.
"Your wife showed me some of them." Mom said, calmly. "Don't worry," she added, trying to calm my nerves, "your s****r was in the bathroom and she didn't see any of them. She doesn't even know there are pictures."
"Shit." I said, slumping back in the bed.
"So, what does that mean – when you said it wasn't entirely correct that you wanted to be a girl?" Mother asked.
I swallowed hard and looked up at her. "Talk to me, Sweetheart." She said, kindly. "Take your time, there's no rush."
I realized I had nothing to lose now. She had seen at least some of the nasty pictures of me in my lingerie and she had obviously been reading my stories. So, I began to explain to my mother, in the best way I could, how it all happened.
I started out by reassuring her I was happy being a male, but, I explained to her that I somehow felt cheated that I couldn't enjoy some of the pleasures females enjoyed, like wearing soft, pretty lingerie and frilly things with ruffles. I told her that ideally, I'd love to be a man by day, and be feminine by night. Then, I went on to tell her my sex drive wasn't that of a typical male and I'd always been disappointed with every sexual relationship I ever had.
"It's like I can't get any real emotional satisfaction with sex." I explained. "No matter who it was, it was never really satisfying. It always left me feeling unfulfilled and cheated."
A tear appeared at the corner of my Mom's eyes and she said, "I know how that is, Sweetheart. I lived with that for years with your father. So, I know the feeling, believe me."
I told her that with Beth, I could perform physically, but, I was just going through the physical motions with her. I didn't get any real pleasure until I sat down and started writing – where I could be myself.
"I understand." Mother replied, softly. "So, tell me, what is the real you, Tom? What is it that you need so badly?"
I blushed when I told her. I just came right out and said it. And when the words started, they ended up being much easier to say than I ever expected them to be. In fact, it was like the weight of the whole world was being lifted from my shoulders as I finally talked openly, for the first time in my whole life, about my sexual desires.
"I am what they call a Sissy, Mom." I said. "And, a Submissive."
I told her everything. I told her it used to hurt to admit that to myself, but, it didn't hurt anymore because I knew it's the truth. I told her I could be a sissy and a submissive in my stories. I could live every desire and every fantasy on paper....... I could wear the frilliest panties, and I could walk around in them all day if I want to.
I turned red when I told her I could let my mother or my s****r dress and undress me, even see me naked because that's exactly what a sissy and a submissive would do. I explained that in my writing, I can give up control and let others make me do things – nasty things.
"What I need is pretty simple, Mom." I said, finally answering her question. "I need a woman that will accept me as a Sissy and a Submissive, and let me live like that."
She sat there and listened intently as I spoke, explaining to her without being too graphic. I tried not to intentionally shock her, but, when she didn't say anything, I was afraid I'd said too much.
"You're not saying anything." I said, quietly, as she just sat there. "Did I shock you?"
"Oh, no." Mom replied. "I'm not shocked; I was just impressed at how open and honest you were. Some of what you said I already suspected from reading your stories, but having you explain it makes it clearer, and, I can understand why you're not emotionally satisfied with your sex life."
"Those stories you read," I added, "that's the real me. I hope it doesn't break your heart to hear that, but, it's true. I'm a sissy....... a submissive sissy."
"A Sissy, huh?" Mom asked. "I saw a story with the word, 'Sissy' in the title. What was it?"
"Mommy's Sissy." I said. "It's something I wrote a long time ago, too."
"Is it about me?" Mother asked.
"Yes." I answered, too ashamed to look at her. "And me, too." I added.
"Ah," she replied, "I see."
"And, uh..... I treat you like a sissy in that story?" She asked.
"Very much so." I answered. "You should probably avoid reading that one. It's pretty graphic and intense."
Mom smiled and took another sip of her coffee. Then, she said, "How do you know I haven't already read it?"
I laughed and so did she. Actually, we both chuckled for a few seconds and you know, I truly had no idea if she'd read it, or not.
"So, tell me," Mom said, as she sat her coffee cup down in her lap, "did your s****r give you panties to wear with that nightie? Like in that story we read at your apartment last night?"
My cheeks started to burn, and I felt a serious blush cover my chest and face. Mother sat there quietly and waited for me to answer, and when I did, the best I could do was nod my head up and down and mumble, "Yes."
"Let's see what she gave you." She said.
I heard her words, but, I didn't tune in to what she said, and as I lie there trying to decide what I should do, my mother reached out and pulled the comforter down to my feet and then reached back up and pulled the sheet down, too. I started to rush to cover my panty covered crotch, but I figured what the hell, after what I'd said to her, and what she'd read, what's the use in hiding the fact I was wearing panties. At least I didn't have an erection.
"They look cute on you." She said, as she looked at the panties around my hips. "I can see why you might feel cheated you don't have underwear like this to wear."
I watched as she sat her coffee cup down on the floor beside her chair and stood up next to the bed. Then, to my surprise, she leaned over and tucked her fingers into the sides of my panties and looked up at me.
"Lift up." She said softly.
Mysteriously, my hips did exactly as she asked, and when I lifted up, she pulled my s****r's panties all the way down my legs and past my feet. Then, sitting back down in her chair, she sat the panties down in her lap and looked at me.
"I wasn't sure I could do this when I came in here." Mom said. "But, I'm sure now."
I was lying on my bed with the covers pulled down and I was now naked below the waist. In the three or four seconds after she pulled the panties off me, I started to panic not knowing what she was up to, but, once she rested for a few more seconds, she took a breath and said, "I'd like you to masturbate for me, please."
She must have seen the look of terror in my eyes, because she immediately spoke again, saying, "Tom, I read in one of your stories that you wanted me to wake you up in the morning and make you masturbate for me."
I was so ashamed at that moment. She made it sound like she was taking pity on me – doing this only because her son said he wanted it. And that made me feel like an absolute ass.
"I'd really like to watch you, Sweetheart." Mother said. "Do I have to ask you again?"
Slowly, my hand started to move to my flaccid cock and once it got there, Mom reached into the pocket of her robe and pulled something out.
"Here," Mom said, handing it to me, "maybe these will help."
As unbelievable as it was, she'd just handed me a balled up pair of panties, and, as I shook them out to look at them, my cock began to harden.
"I wore those to bed last night," Mom confessed, "and I had them on while I was reading your stories."
Immediately, I raised her panties to my nose and inhaled deeply. At the same time, my cock went to full hardness, and when I looked over at her, she was staring at my cock as I slowly moved my hand up and down.
I stopped stroking for a few seconds and held it still for her, allowing her to see my fully erect cock for the first time.
"You have a beautiful penis." She said, almost whispering. "And, I want to go all the way for me, Tom. I want to see you ejaculate."
I held my cock still for her for another few seconds and then I started stroking my cock again, very slowly but quite deliberately. Her gaze shifted back and forth between my cock and my face, and when she'd look up at me, I took a big sniff of her panties,
"Here," she said, moving from the chair to the bed, sitting next to me, "let me help you with that."
I just about died when she took her panties out of my hand and opened them up to find the crotch panel and then pushed the cotton fabric of the gusset right against my nostrils.
"Take all the time you want, Sweetheart." She whispered. "I'll stay with you as long as it takes...... until you get done. Just tell me if there's something I can do to help."
I had to be dreaming – or something. Never in my wildest dreams would I ever have expected to have my mother holding her panties up to my nose while I was jacking myself off.
After a minute, she moved slightly on the bed, readjusting herself so she'd be more comfortable. When she did, she changed hands so her left hand was holding her panties up to my nose and her right hand was gently resting on my chest.
My hand was stroking my cock nice and slowly and it felt so good. I glanced up at her a few times, and each time I looked, I could see she was staring at my hand stroking my swelled member. I can't explain how good that made me feel – the fact that she was looking at my cock. I guess I felt that if she was disgusted with me, or repulsed by my stories, the last thing she'd want to do is see my cock, but, the look in her eyes was more than that, and unless I was wrong, Mother was definitely interested in what she was seeing, and what I was doing.
My pace started to increase and as I jacked faster, Mom slipped her right hand under my nightie, rubbing my chest lightly until she found my nipples. Very softly, she began to finger my nipples, circling them with her fingertips and then touching them very lightly. She alternated between both nipples, moving her hand across my chest as she did, touching me in a way no other woman had ever touched me.
"Does it feel good when I do that?" She asked, whispering softly. "When I touch your nipples?"
"Oh yes." I said, breathlessly.
She pulled her hands out from under my nightie and pushed the silky garment up, bunching the soft material under my chin and baring my chest. Then, she bent down and began kissing my nipples, running her tongue around each one and sucking my nipples into her mouth. The feel of her hot breath on my chest was exquisite – and it felt incredible. My head rested back on the pillow and I simply let myself go and enjoyed it all - the feeling of her warm breath on my skin, her kissing my nipples, the smell of her panties and the sensations coming from my cock as I jerked myself.
I found myself actually moaning under my breath as I stroked, and whenever I moaned, Mom made little sounds in return, as if she was telling me it was okay to enjoy it. This was a new sensation for me; I've never had a woman touch my nipples with this kind of tenderness, and I would have been more than happy to relax back into the soft bed and just let her lick, suck and kiss me there as much as she wanted.
But, as much as I would have loved to enjoy my mother's mouth on my nipples, my cock was in need of attention and my hand was flying now, rubbing up and down my pole in an urgent manner as I sniffed in the smell of her vagina – my own mother's vagina from the crotch of her panties. Her scent was different from the smell of my wife's pussy and different from the smell of my s****r's. Maybe it was her age, or maybe it was something else, but, whatever it was, it was stronger and it was robust...... and I loved it.
She took one of my nipples into her mouth and she sucked it hard, flicking the tip with her tongue. The feel of her hair falling all around me sent a plethora of sensations raging through me, and I knew it wouldn't be long before I started to cum.
I started panting, wildly breathing in and out as I pulled up and down on my cock. Mom sat up and looked down at me.
"Tell me when you're close to ejaculating and I'll help you finish." Mom said, looking down into my eyes. Then, as she went back to sucking my nipples, I closed my eyes and let all the sensations that were flooding over me have their way. And, it wasn't but another minute or so before I got that feeling to tell me I was dangerously close.
"I'm close." I whispered, urgently, trying to get her attention before it was too late.
Mom's head lifted up and she smiled at me as she reached her hand down and hovered it over my cock. "Tell me when." She replied. "Then move your hand and let me do it for you."
"FUCK!" My mind screamed when I heard her say that, and that's all it took.
"Now." I gasped, as I let go of my cock and pulled my hand away.
When I felt her wrap her fingers around my cock and grasp my pole, her touch was as light as a feather, but when she started jacking me, she tightened her grip and then began stroking me.
"Come on, Sweetheart." She whispered. "Let it all go for me."
When my first spurt exploded from the head of my cock, the contraction was so intense, the top half of my body involuntarily raised up off the bed. But, Mom didn't stop jacking. I could see a smile break out on her face as ribbon after ribbon of hot, thick cum erupted from my cock, splattering small globs of sticky sperm against my chest, neck and even my face. I was moaning and groaning as she handled me, varying the tightness of her grip and how far up or down she stroked. And you know, she was giving me a better hand job than my wife ever did.
When it was over, I was totally exhausted, panting and puffing, trying to catch my breath.
When I opened my eyes, Mom was looking down at me with a major smile beaming from her face. I could see her looking down at the pools of thick sperm that peppered my body all the way from my belly button up to my cheeks. I'd had a serious penile eruption with a massive spread pattern, and I think she took great joy in the fact that she'd aroused me so much to make me cum like that.
"Tom," she said giggling, "you are literally covered with semen."
"I'm not k**ding, Sweetheart," she laughed, "there's pools of it all the way from your stomach up to your face. I guess I did a good job, huh?"
"Mom," I said, trying to speak between breaths, "that was probably the best hand job any one has ever given me. And, what you did with my nipples....... that was wonderful."
"Well, thank you." She said, proudly. "Your father would never let me touch his like that," she added. "he just wanted to get between my legs and a few pushes later, it was all over. So, you probably won't understand how nice it was to do this for you, and to see you react the way you did – it just makes all the difference to know I can bring a man pleasure."
Mom leaned down and kissed me lightly on my lips and then pushed herself up. Then, using her panties, she began to wipe the cum from my body, turning her panties as she needed to in order to wipe up all the globs of sperm that covered my skin.
"Just relax and let me see if I can get some of this cleaned up." Mom said, cracking a smile as she spoke. "I guess we both know it's probably not a good idea just to hand you my panties and trust that you'll clean yourself off, and then put my panties in the dirty clothes."
It took me a second, but, when I got her joke, I started to laugh myself. And, as she wiped me down, she'd touch my chest lightly with her free hand and she'd look into my eyes for a few seconds and then she continue with what she was doing.
"I'm curious....." Mom said.
"How was it?" She asked. "Me waking you up and having you masturbate for me? Was it as good in real life as it was on paper?"
"Honestly, Mom," I said, "I ought to rewrite that story and include exactly what you did because it was perfect. And Mom," I added, "I should either beg you to give lessons to my wife, or, just move back home for good. I don't think a woman has ever made me feel those kinds of sensations before."
I could see the satisfaction and delight in my mother's face as I complimented her. Her eyes were sparkling and there was a glow about her that I hadn't seen for a long, long time.
"That's flattering, Sweetheart." Mother said, batting her eyes as she smiled at me. "But, if you can't patch things up with Beth and you need a place to stay, you know you're always welcome here, and we'll try to work something out about..... you know..... what you need from a woman."
To be continued.