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Title: Becoming A Pantyboy
I used to bicycle to and from work, twenty miles each way, so I wore bicycling clothes after work hours.
One Friday night after the factory closed, I changed into my shorts. On the lunch table, under a newspaper was a girlie magazine. I thumbed through it. There was a picture spread of Candy Samples who had not only a good figure but one of the most beautiful bushes ever. On the third page, she was sprawled on a sofa, with her legs apart as she worked a pink vibrator in her pussy.
I was turned on, and about to go back between the lockers to jack off, when I heard Lois, my secretary, walked up behind me.
Lois was in her fifties, twenty-six years older than me. She always wore tight but never revealing clothes, which made no secret that she too had large breasts. That day she was wearing a tight black skirt, which, when she stood up, puckered provocatively just below the gentle swell of her belly over her mound, and a moss green blouse. She had her gray hair up in a bun.
I quickly turned the page. I was embarrassed to be seen looking at a picture of a woman masturbating.
Lois stopped next to me. I held my helmet in front of me, hiding my erection.
?Big boobs,? Lois said, breathing the words into my face. She pressed lightly against my arm. ?Nice bush too,? she whispered so quietly that I?m not sure if she said anything or just breathed into my ear.
I moved my helmet a little more, trying to make sure Lois couldn?t see how excited I was. ?The guys shouldn?t leave this stuff around,? I said, and started to close it.
She put her hand on mine and pulled it away from the magazine. ?Men will be men,? she said, reaching past me and turning the page. My heart pounded. We both looked at the picture of Candy Samples, spread wide for us, with her hand on the large vibrator pushed up inside her, as she pleasured herself. Lois turned a little, locking my arm between her breasts. ?Mmm . . .? she hummed, ?and women will be women. . . . Don?t you think?? She reached down and took the helmet away from me, ?I can?t see past it.?
For a few minutes neither of us moved. The shape of my hard-on and my balls were outlined clearly in my shorts.
?More?? Lois asked as she turned the page. Candy Samples was kneeling on the sofa, facing the camera, smiling as she licked the vibrator. ?Of course,? she laughed quietly, ?a real cock is nicer.?
I turned to face her. Her hazel eyes sparkled in the crimson light of the set-ting sun.
She took my hands and, as if I might pull them away at any moment, care-fully put them on her breasts. ?I have big boobs,? she said. It was statement in which hung the question, do you like them? Want them?
We looked into each other?s eyes while I felt her stiffening nipples through her blouse. I began to finger them, softly rubbing and pinching, making them harder.
?Yes,? she sighed.
?These are much nicer than a picture,? I said.
She smiled and taking my head in her hands she pulled my mouth to hers.
We kissed. I slid my hands around her and pulled her to me. Her breasts mashed against my chest. Our tongues danced wetly. She pushed her hips into me and pressed the swell of her tummy against my stiffness. ?Mmm,? she moaned, ?and men will be men.?
My hands drifted down over her ass. I was dizzy with lust for her. I started to grab at her skirt, wanting to pull if up, wanting to possess her.
She pushed away from me. ?Not here. Please,? she whispered, ?come home with me.?
Her blouse had opened, and the fleshy mounds of her breasts heaved with her own desperation. I reached for her.
?Please?? She took my hand and placed against her face. It was wet.
?Don?t talk. Don?t say anything. Just come with me.?
We put my bike in the back of her car, and drove across town to her house. I stayed quiet as she asked.
Her skirt rode up while she drove, enough for me to see that she was wearing real stockings and a garter belt. I wanted her more each minute.
?Did you know I was married? Twice. My first husband,? she hesitated, her voice full of pain, ?used me. He was an alcoholic and divorced me after three years. My second husband was sweet. He taught me other things. We had a child.?
I could see tears on her cheek in the dim spill of the street lights.
?He would have been about your age. They died in a car accident.?
I started to say I was sorry.
We drove in silence for a minute.
?I?ve wanted you since you first came to work. But I won?t be hurt again. Do you understand??
?Yes, I think.?
?Will you spend the night with me??
?Yes or no??
?Yes, oh my god, yes.?
She smiled at me, ?Good boy.? We turned into her driveway.
Her kitchen had small mood lights, which made it feel cozy. I set my stuff down on the counter.
?Oh, shit,? Lois said as she saw her laundry on the table. ?I was folding?
?It?s okay,? I took her arm to stop her. ?I don?t think you should be embarrassed at my seeing your,? I hesitated because suddenly the word had new importance to me, ?panties . . . and things . . . I mean?
?I guess not.? Lois laughed. ?Let me finish folding, then? she kissed my cheek and sat down. I sat opposite her. Her face flushed as she began to fold her lingerie. We made small talk mostly about the summer storms work problems. But I couldn?t keep my eyes off her lingerie: panties, bras, garter belts, and sleep-wear. Not only did I like looking at it as she held and folded each piece, but I started to think about what she looked like in it.
She saw that I keep looking at her underwear. ?You like my panties??
I felt my face burn with embarrassment. I had always like pictures of women in panties, and I enjoyed peakingalthough I did try to be discrete.
?These,? she pulled out a pair of maroon lace bikini from the pile, ?are quite scanty,? she said holding them up. ?Lace edging around each leg . . . a little satin in the . . . crotch,? she blushed, too, ?for my . . . pussy.?
She held them closer, and I wanted to touch them. Shame and lust seemed to fill my lungs. I looked at her, hoping she would either stop teasing me or . . . or . . .
She stood up and moved around the table in front of me. She smiled. ?They are quite so revealing.? She touched them to my lips. ?The lace is open, and they are so small, you can see almost . . . everything.? I closed my eyes, savoring the moment. She knelt next to me, holding her panties to my face, leaning close, her other hand on my thigh, she whispered, ?Are you my pantyboy??
The words seemed to offend me because they resonated with the truth. I wanted to deny it. I opened my mouth to say no, but she held her panties against my lips tightly. ?Darling, I want a pantyboy.? She kissed my neck. She turned her panties in her fingers so the satin crotch was against my lips. ?This is where my pussy touches. You want my pussy, don?t you??
I shook my head, yes.
She was kissing my neck and ear, moaning and whispering. ?You want an older woman?s pussy.?
I opened my eyes, the words startling me. She was staring at me, our faces inches apart. My heart raced. My god, she was rubbing her panties over my face, a woman twice my age. She seemed to know more about my deepest secrets than I did, and I could only want her more and more.
?You do, don?t you?? She took her panties away from my mouth.
?Yes,? I whispered.
?I want you . . . Lois, I want you so much.?
?I know, and I want you more than you will ever know. But now, you have to tell me.? She dropped her hands to my thighs, rubbing and squeezing them. ?Can you understand? I want you to tell me what you fantasize about . . . what about my body excites you most . . . what about me excites you . . . I want to know your lusts and feed them and nurture them. I want you to want me with all your soul. I want to pleasure you like you have never been pleasured.? She leaned down and kissed the bulge in my short. ?Because in return you will worship me, my special panty boy.?
How could I say even the words, let alone admit such secrets.
Her face nuzzled against my cock and balls. ?Tell me.? She kissed my balls through my shorts. She licked them, wetting my shorts with her saliva. Her hands gripped my hips. ?Tell me.?
?I?ve . . . masturbated . . . thinking of you.? I watched Lois, kissing and licking me, looking to see if she would be shocked.
She turned her head to look up at me. ?Yes. Oh, my god, yes.? Kneeling at my side, she pulled her skirt up and slid her hand under her dress. ?More, tell me more.?
?Lois, . . . it?s . . . embarrassing.?
She looked at me.
?Honest, I . . . I just can?t.?
Lois stood up and turned away from me. It may have been only seconds, but it felt like hours.
?I?ve never talked like this to a woman before,? I said. ?I?ve never talked about my fantasies.?
?You just want to fuck me because I?m better than jerking off in the locker room.?
?What?? She turned towards me. ?You like me throwing myself at you? I?m old enough to be your mother, and what am I to you? An old cunt desperate young cock??
?No.? I really had fantasized about her, a lot. ?Lois . . . ?
She lifted her skirt. ?Is this what you want?? She pushed her panties down, exposing her large, brown bush. ?This??
I didn?t know what to say.
?I know, you want Candy Samples.? She tore at her blouse, several buttons dropped to the floor as she angrily took it off. ?More?? She glared at me as she unzipped her skirt and shimmied out of it. ?Not enough?? She unhooked her bra freeing her large breasts. ?Nice??
?No? Not enough? Here.? She pushed her panties all the way down and tossed them at me. Then she sat back on the table and spread her legs. ?This is what you want.? She began rubbing her pussy. Tears streamed down her face. ?Go ahead, you got your wish.? She spread her pussy lips. Her anger made it obscene. ?Well? Jerk off. No? Maybe you need a locker room for that.?
I stepped towards her.
She put her foot up on the table, exposing herself more.
I dropped to my knees. ?Lois, please.? I put my hand on her stockinged calf. ?I?
I lifted her foot and kissed it.
?I?m sure you?ll tell your buddies about this. How an old bitch slutted for your young cock.?
I looked up, trying not to look at her pussy. Tears had filled my eyes.
?I . . . love you,? I whispered. I clasped her foot to my mouth. It was, I realized, the truth.
Lois put her other foot down, and moved her legs together. Hiding her special place. Her chest began to flush. ?You can?t mean that.?
?I do.? I reached around and gathered up her clothes. ?Please,? I handed them to her, ?I want to make you happy. I want to pleasure you. But not like this.? I looked into her eyes. They had softened, her anger was gone.
She turned from me to dress, suddenly shy and she admitted later, embarrassed by her outburst. I continued to kneel, watching her pull her panties up, put on her bra, her skirt and her blouse. She held it closed when she turned back to me. ?I guess I need a new blouse.?
?I?m sorry,? I said. ?Tell me what you want, and I?ll try.?
?Can we be many things??
?I don?t understand.?
She knelt in front of me. ?Can it be new each time?? She took my hand in hers. ?Can we be man and woman, lovers??
I touched her lips with my finger tips. ?Yes.?
?Can we be mistress and pantyboy??
I slid my hand over her cheek, wiping away her tears. ?Yes,? I whispered, my
?I might dress you.?
I lowered my eyes, ashamed at the answer I knew I wanted, ?Yes.?
She placed her hand on mine. ?Can mistress become . . . mother . . . and lover become . . . son??
I leaned down into her chest, wrapping my arms around her, my face pressing against her full breasts. ?Yes,? I whispered. She put her arms around me. And kneeling there, together, rocking back in forth in ecstatic bounding, our hearts race in unison, I whispered even more softly, ?Yes . . . mommy.?
After a light salad and a glass of wine. She asked if I would straighten up the kitchen for her. She said she would leave me night shirt and a towel in the guest bathroom, and that she needed to soak in her tub. I didn?t ask what she wanted afterwards. Having seen her anger earlier, I did not dare to presume anything.
The house was dark when I finished in the kitchen. There was no night shirt in the bathroom, but I decided I could wrap myself in a towel. As I showered, wondering what the night would hold, although my balls ached, I felt good, something important had been, if not resolved, at least made open. After I dried myself, I found a shear white lace and satin sleepshirt folded in front of the door in the hall. It had Lois?s perfume on it, floral and fresh. As I picked up the shirt, the maroon lace panties Lois had teased me with earlier fell out. What did she want?
?I might dress you,? she had said. The shirt was cut low, and would have been sexy on herher breasts would have been barely covered with sheer white and her cleavage accentuated with the lace-trimmed V collar. My hands shook as I buttoned it.
Then I picked up her panties. They were moist with the scent of a woman?s arousal. I had never acted on my fetishonly sissies play with panties, I had told myself. But now, Lois not only had given me permission, but she was encouraging me.
I held them to my lips, as she had. She had used them to masturbate her-self. My heart raced as I turned them inside out, and kissed the inner panel. I could taste her. I could taste Lois?s pussy. I closed my eyes and savored her natural fragrance. I licked her moistness and wiped it over my face. I wanted her so badly.
?I might dress you,? she had said. I was wearing her sleepshirt . . . Could I? I wanted to. I wanted to feel the on me. Like a second skin, a woman?s most intimate skin, magically inherent in the lace and satin. I heard myself say the word, panties.
I started to put them on. I was frantic. I got harder as I pulled them up. De-spite the lace ribbon around the leg openings, the cut was such that they could not cup both of my balls, I tried to push one ball back in, and then, my hand was on my cock. My swollen cockhead stuck out of the waistband. I cupped myself. My hips jerked. ?Oh, God!? And I exploded.
As I stood, numb with the suddenness and power of my orgasm, my sticky cum ran down my stomach, wetting my panties. I felt ashamed. I felt proud. I had tears in my eyes. My chest ached with the poignancy of a hundred emotionsthe deep arousal of a permitted fetish and the feel of taboo lace against my skin, the shame of having my secret acknowledged and the joy of Lois?s gift.
Should I wash them? Should I tell her? I looked at myself in the mirror. I was flushed, breathing hard, wearing panties and a lace sleepshirt. And I knew, I needed Lois.
I turned off the light and walked to her room. The door was closed, so I knocked softly. ?Lois?? There was no answer. ?Lois? Silence.
?Can we be mistress and pantyboy??
?Mistress?? I whispered, knocking again. ?Mistress??
I thought, hearing myself say ?Mistress.? Taboo feelings swept over me like a typhoon. Lois was not just a woman, an older woman. She was fertile, mistress, mother, goddess.
?Sweetheart,? Lois said, ?come in.?
My hands shook as I opened the door. Lois was sitting up on the bed. She was wearing a lilac colored silk gown, which was loose, low cut, and long. It was simple but sexy on her.
I stood in the doorway.
?Show me,? she smiled.
I felt my face redden, but I walked into the room, and turned, letting her see me in her night shirt and panties. I was shamefully aware of the now cold sticky cum.
?And my baby?s panties??
?I . . . I . . .?
How could I just say, I was so excited by your panties, that I came when I put your panties on?
?I . . .?
?I masturbated in those panties, and I gave them to you to wear. And there you stand, wearing them . . . wearing my panties. What can?t you tell me??
Panties! Hearing Lois say the word was exciting. She looked me. I lifted the sleepshirt an inch or two. She could see I was wearing panties.
Lace and satin panties are cut to accentuate a woman?s hips, ass, mound, and pussy. Panties were meant to gild a woman?s sex. To tease. To hide a mystery. And I was wearing panties. Lois?s panties!
I blushed, I was wearing panties. A man. Engorged with lust, his cock, my cock, stiff and flared with the need to possess, the masculine imperative. And yet there I stood, shamefully wearing lace panties, so symbolic of the feminine, making my cock and my lust an obscenity, knowing that part of my arousal was due to wearing panties for Lois.
I came for you, and now I?m aroused for you, I thought. See me! See my cock! For you. I lifted the night shirt, and stood for her. The cool night air hit the red velvet tip of my cock. The wet spot clearly visible. My hips involuntarily thrust, desperate to feel friction against my cock.
She smiled at my lust. Her eyes ran up and down me, lingering over my cock, bulging out of her my panties.
?You are my pantyboy. You squirted in them.?
?Yes,? I whispered, ashamed too that I didn?t, couldn?t, control my excitement.
And at the same time, I was proud of my erection for her.
?Come here and give . . . mommy . . . a kiss.?
My heart raced, mommy. I walked to the side of the bed and leaned down to kiss her. As her lips touched mine, she whispered, ?I can smell mommy?s pussy on you.?
?Yes,? I whispered, ashamed at admitting to the obviousI had rubbed her moist panties over my facewanting her scent on me. ?Thank you for the panties.?
Her had rubbed my back through the nightshirt. ?Mmm, so sexy . . . my sweet pantyboy.?
She sat up. ?Milk me,? she whispered. She pushed the strap of her gown down and pulled out her breast. Holding in her hands, she looked at me. ?Let mommy feed you.? ?Please. Please.?
I crawled up onto the bed next to Lois. Snuggling close, I let her guide my head to her breast. I opened my lips for her nipple, and gladly suckled. I was aroused, but this was more a sensual act than sexual. It is what Lois wanted, and I was stunned at how much I wanted to give her this. As she sighed and stroked my head, calling me her baby, her pantyboy, I savored the smell of her perfume, dabbed between her breasts, the feel of her rubbery pink nipple in my mouth, and the almost instinctive urge to suck and be comforted.
She talked to me as I suckled. ?When I was just out of high school, I got a job as an executive secretary. I felt very lucky, and almost worshiped my boss. After a few weeks, he asked me out, and couldn?t have said yes fast enough. That night he made love to me and I lost my virginity. Six months later we were married. He blamed his drinking on my reluctance to be more open sexually. I yielded to him. He took me to parties, where?
She paused to take out her other breast and move my mouth to it.
?My baby is hungry,? she said caressing my cheek. ?Mommy was used at those parties. I had to take my clothes off and play with myself, and they laughed calling me names. I was fucked by everyone, in my ass, my mouth, my pussy. The parties got bigger, and the men often brought their wives. I was displayed. I was made to beg for cock . . . for pussy. Some of it . . . I liked . . .?
She slid her hand down to her pussy and began to rub herself.
?But Doug hurt me too. He?d get drunk and beat me. The last time I saw him, he made me walk two blocks home from one of their parties, naked and covered with cum.?
Her hips began to gyrate.
?Baby, suck mommy?s tits.? Her fingers moved faster. ?Yes.?
Lois came, screaming and bucking. I kneaded her breasts. Sucking hard. And when she was through, I just wanted to hold her.
We fell asleep like that.
Early in the morning, I awoke with Lois kissing and sucking on my cock. I moaned. My balls still ached, but how good it felt. She cupped them softly in her hand and kissed them. ?I want your sperm,? she whispered, ?your seed.? She licked my shaft and flicked her tongue over my pee hole. ?It?s my turn to milk you.? With my cock wet with her saliva and my precum, she stroked me, and watching my face, she slid a finger over my asshole and began teasing it.
?Lois,? I moaned her name. My hips bucked. ?I?m going to cum.?
She stroked faster. She put her mouth over my cockhead and softly ran her teeth over the sensitive edges of my glans. Her finger massaged my prostate as I squirted my cum into her mouth.
And that is how I woke up at Lois?s on a my first Saturday with her . . . and became a pantyboy
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