Vivian's Best Kind of Girlfriend

I feel that the age we live in is nothing short of remarkable. Sure, we can bemoan the demise of things past, like ground shaking muscle cars, public indoor smoking and the like but let's take a fresh look at the Internet. We sure wouldn't have a venue for things like this erotica site back then, not to mention all the unique people we share ideas with online either.

I first went online on a free trial basis only to activate a popular DVD burning program. I did so to be able to copy rented movies. Out in the country it was impractical to rent just one and I'd run out of time and end up with speeding tickets when trying to meet the return deadline. My free trial account included chat room access which I more or less stumbled upon.

I ended up keeping the account and became a paying network member ever since. The chat room I found led to other chat rooms and I became an addict of sorts. I bought a webcam and spiraled downwards into a world of sexual depravity and subsequent despair that took me a long time to recover from. I'm doing much better now and this story writing site is the wildest thing I do these days. The topic of this story is one situation I found myself in as a result of my use of a rather tame, non-sexually themed chat room I used to frequent.

I've always been the sort of person who felt, well...'old' on the inside and I ended up being a chat regular on a room dedicated to mature chat people. They were more sincere and shared more of my interests and attitudes than people my own age. One night I started talking about my being banned from the public library system and one lady and her friend started joking around about a solution to my problem. I had said I didn't want to enter the library to ask about my outstanding fines because I might be arrested by 'library cops'. I was kidding, of course.

My lady chat friend, let's call her Vivian, was a divorcee of about fifty years of age and a local. She suggested I go in disguise. Her friend, a lady of about the same age, said "Yes, as a woman though..." The second I read the text on the screen I felt a shock run through me and I became sexually aroused. When I was younger I had experimented with cross dressing and still thought about it from time to time. I was aware that others were reading this conversation and there was nothing I could do to stop the humiliation from continuing. This led to me blushing and becoming even more turned on. I reached down to adjust my throbbing erection in my underpants, giving it a firm tug in the process.

Vivian continued typing, "I can see him now, all dolled up, strutting down the street in stockings and heels!"

Her friend, Dawn, added, "Better give him a sexy dress and a blonde wig too...don't forget that, lol. I bet he'd look really cute." I sat and read the screen, dumbfounded. My hardened cock strained for release.

I had been idle for too long and thought I'd better type something or be suspected of wanking. "'Hey you guys, thanks for the compliment but I'm getting a swelled head," I added hastily. Far too hastily as it occurred to me just as I clicked the enter key. Oh no...

I leaned back and undid my belt, pants button and zipper as I waited for the results of my careless choice of words. What followed was what one could expect from line like that. "Aha, looks like we've got a live one here. He wants to dress up and give all the construction workers hard ons," typed Vivian. I re-read the words aloud and couldn't resist pumping my solid shaft and bulging cock head a few times. I circled my thumb around the tip, well lubed by pre-come and continued reading.

Dawn added, "He's a very bad boy, better spank him, lol."

Vivian typed, "Let's both spank him, don't forget to lick your hand first, hurts more that way." That did it. My orgasm started before I even managed to grab my pulsing rod. I stroked it as my sperm shot out of my cock, nearly flooding the keyboard in the process. I was still ejaculating as I groaned and groped around for a paper towel.

I continued the chat conversation the best I could, all things considered, not wanting to let on that I had just released a gigantic come shot, thanks to them. I couldn't, for the life of me, get over the image of me dressed in women's clothes and laying across their laps as they spanked me. I imagined these two voluptuous and mature women taking out their frustrations on my quivering ass while denying me my masculinity.

I skipped the chat room the next evening. Instead, I shaved my legs and found my lady's clothes collection. With shaking hands I selected a few of my favorite items. I donned a black, frilly slip, lacy high cut panties and stockings. I loved fastening the stocking stays and straightening the dark seams up the backs of my legs. I sheathed my erection in a condom as an afterthought and pulled my panties up tightly, forcing the black panties' lace front up around my balls and base of my cock. I laid back on the bed and admired my crossed legs and how my the flesh of my thighs swelled slightly above my elaborately patterned stocking tops. It had been a while since I last did this sort of thing but I was definitely enjoying it. Last night's chat was giving me renewed interest, I suppose. Thanks again ladies..

I maneuvered my impossibly tensing man shaft in between my crossed legs and began slowly gyrating my hips in circular motions. I caressed my lingerie clad body as my aching penis sought release from the grips of my clenching thighs. My fingers lingered over the garter strap fasteners as my thighs rolled my trapped cock back and forth.

I slid my hands under my stocking tops and raised my long, curvy and pressed together legs upwards. I reached around and slapped my ass hard a few times. I felt a sensual flood of warmth spread through my abdomen and my privates. With one last trembling pelvic thrust my slowly building orgasm crescendoed and I began spurting a huge load into my condom. I gasped deeply in response to the hard contractions between my legs and the gushing of my semen into the latex sheath. The sense of release was incredible, all intensified by my wearing ladies' unmentionables. This was the closest I could get to enjoying and exploring a real female body. I reflected on these thoughts as I recovered from my climax.

I quickly cleaned myself up and rolled over onto my side and fell into a deep sleep. I was still wearing my sexy lingerie and was a bit surprised by the silky feel of it all against my body on awakening. It wasn't really a full night's sleep I'd had, more of a long nap. My cock was semi erect and had escaped from the constrictive holds of my black panties. The panties' narrow crotch had a testicle showing on either side as well. I got everything back into place and sat down at my computer, crossing my legs as I did so, just for fun.

I thought briefly about putting on an anonymous web cam show but decided against it. Eventually someone would want to see pink and I didn't want to disappoint. Instead I opened my internet account page and saw Vivian's private message. She was concerned that I was still insulted and had quit the chat room. I answered that I wasn't.

"I wasn't insulted, quite the opposite," I reassured her.

Vivian responded, "Oh good. Wait a minute, does that mean you're into that stuff? Wow."

"Lol, I've never told anyone before. In fact, I'm in that stuff as we speak," I quipped.

"Oh really?!?! Cam please?"

As I tell this, looking back I can't believe I did what I did next. Not only did I admit to cross dressing but I turned on my web cam and gave her a brief look at my sexy ensemble. She got to see everything but my genitals. I even bent over for her and patted my ass cheeks teasingly. I was still sleepy and in a trusting mood. I felt very odd as I did this cam show for her. She didn't own a web cam and I had no idea what she looked like or even if she was a woman. Still, it gave me a thrill to show myself in this new way. I waited for an uncomfortable number of minutes for her typed response. I nearly fainted when I read her message, "I sent my house address to your email. Get over here now!"

Throwing all caution to the wind, I ran around the room, franticly getting changed into my regular clothes and finding my truck keys. I stuffed my sexy underwear items into my coat pockets and went out to meet Vivian in person. On the way to Vivian's, I had a bad case of butterflies in the stomach and I considered turning back. My curiosity and my swelling sex member kept me going forward.

I parked and knocked on her door. Much to my relief, she was a fine looking woman and lacked any sort of crazy vibe...well maybe a little crazy to invite a virtual stranger over but she smiled and invited me in just the same.

I sat there making small talk as she put out tea and cookies, as if there was nothing at all unusual going on. My nervous energy was rapidly fading and I felt suddenly very self-conscious. I looked her over as she carried a tray out of the room. She wasn't thin like a model, not tall and thin like the porn queens of the Internet. Instead she was of medium height and had exaggerated and pronounced curves contours, giving her a strong, powerful look. Her face was faintly lined and framed by thickly curled, dark hair. I also noticed her pretty hazel eyes. She gazed at me warmly as we conversed about the city road conditions and the weather, all the topics people usually talk about.

I had nearly forgotten what had prompted the invitation when she looked down silently. I said nothing. Still looking down, she covered my hand with hers. I sat still, save for instinctively stroking the top of her hand, waiting for her to speak.

"I loved your cam show. Thanks. I was shocked at first, but thanks anyway," she laughed while glancing up shyly.

I cleared my throat and answered, "To tell the truth, I'm amazed that I did it too, and that you invited me over."

Vivian looked at my face for a brief while, then brushed the back of her hand against the side of my face. "You're sort of handsome, but I need to make you understand that I don't respond to men sexually. I only like their... well let's just say it...their cocks!"

I flinched slightly and sat upright. We continued to hold hands. She leaned forward, seeking to have our eyes meet and asked, "This is okay, right? We might as well face it, you didn't come here to make me into your girlfriend anyway...am I right?"

I nodded slowly while she searched my eyes for the truth. I spoke without hesitation and told her, "I wasn't thinking about anything in particular. I'm lonely, that's all."

Vivian stood, still holding my hand, and said, "Okay, we understand each other. Will you dress up for me then?" I loved her English accent. She came around the side of the table, gliding more gracefully than I've ever seen anyone do since, and sat on my lap. I shifted uneasily as my erection rose up and pressed into the underside of her as she kissed me. The reality of the situation weighed on my mind as we kissed.

My cock surged with lust as I cupped her breasts and leaned in for another deep kiss. I switched to caressing her knees and then somewhat higher up on her thighs. I was thrilled with her darkly colored stockings and her closely fitted skirt. This was really happening. No hiding behind a computer monitor in some insular, safe room anymore. She was real, I was real, I felt I was in over my head. She ended the embrace and stood beside me. My cock tented in my pants, complete with a growing wet spot of shining pre-come. She noticed it and put her hand to her backside and looked away as she felt the slickness of it between her nimble fingers. She simply smiled and shook her head in amusement. I was planning on an apology but she didn't seem to need one.

She put her arm on my shoulder as she leaned in to whisper in my ear. "Come on, I want to slip you into something more comfortable," she chuckled. Her tone lightened my mood and I couldn't wait to please her any which way I could. I rifled through my coat pockets, collecting my silky women's undergarments, and followed her into the bedroom.

She sat on the edge of the bed with excellent posture. Her sizable and soft breasts rose and fell in tempo with her quickening pulse. Her legs were crossed at the ankles and looked very sexy. I got undressed as she looked on. Her eyes shone in the dim light of the bedroom as she nodded silently in approval as every piece of my clothing hit the floor. She leaned back and crossed her legs at mid-thigh. I looked at her shapely legs with genuine admiration and arousal. She smiled coyly as she rocked her hips and bobbed one foot up and down.

Once I had nothing else to remove, I just stood there. Vivian said, "Don't stop now, this is just getting good. Play dress up for me." She removed her blouse over her head, revealing her black satin slip underneath and the smoothest breast tops I could have imagined. I had a sudden urge to forget my manners and just take her. I fought against my lustful instinct of just pinning her down and forcing my sex into hers. She seemed to sense this somehow and shot a cold stare in my direction.

She stood, placing her hands on her hips, took a few steps towards me and said firmly, "Listen, you agreed to this. I never promised you sex. We're going to have fun together. Don't spoil it. Do as you're told and be my good sissy boy."

I blinked in response to "sissy boy". I was taken aback but grateful that she would be willing to take charge. Without another word she got me dressed. She helped me into my lacy slip and even stuffed rolled up stockings into my bra. She put a blonde wig on my head and carefully applied crimson lipstick and dark, sultry eye shadow. She sighed, "I'd let you look in the mirror but you might like it too much. Look at the state you're in already." She pointed at my sex shaft. It was throbbing shamelessly. I had been wiping growing drops of clear sex fluid away from its head furtively the whole while until now. "Oh well, on with the show," she added wistfully. Vivian decided she'd rather see me in pantyhose so she found me a black pair with a richly laced control top.

"Better to trap that cock of yours. I love your hard on but I can't have you messing up my expensive underwear." She instructed me to put on a condom. The elastic of it cinched too tightly around the base of my cock and made it bulge painfully as she rolled the pantyhose luxuriously up my legs. She gave my aching member a light squeeze and laughed at my lustful groan. She stood back and admired her work and winked at me. She had done her work well and she knew it.

She found a fancy vintage black cocktail dress with tassels around the hem and had me wear a set of shiny high heels. "Turn around for me honey. May I see my new girlfriend?" she asked.

I tried to step as ladylike as I could manage, but I'd never walked in heels much before. In fact, this was the farthest I'd ever delved into dressing up ever before and it felt strangely natural. She caught my gaze and smiled at me confidently. She turned on the stereo and held me tightly in her arms. We started dancing slowly while her face into my chest. Our bodies pressed tightly together as we danced and I, for a moment, forgot I was in a state of full feminine dress.

She sighed and glanced up me. I bent down and we kissed again. It was a slow, deliberate kiss that I'll never forget. Our tongues met as we continued on with our embrace. She backed up to the edge of the bed as she kissed me with growing passion. She fell backwards onto the mattress, pulling me down on top of her. Vivian pulled her slip up around her big, round hips, revealing her stocking tops and gleaming black panties. She moaned as my horny bulge found it's place between the swollen lips of her parted sex. I rocked my hips into her, seeking satisfaction. The friction of my lace clad member against her slippery silk panties sent jolts of sexual electricity through me as she wrapped her thick legs around me.

"Don't stop, oh god don't stop. I can't let you fuck me, just come for me, I'm about to come!" she hissed into my ear in hot, measured syllables. I'd been holding back, but no more. This is what she wanted and I obliged willingly. With one final heroic thrust, I came hard. My pent up seed flooded hotly around my cock's skin, swirling and surging within it's tight, latex enclosure. Vivian's hips bucked uncontrollably against my body. As she held me in a crushingly tight embrace her long, red fingernails dug painfully into my back and her eyes were shut tight. He face contorted in ecstasy as she came.

She whimpered as I rolled off of her. She reached down towards her sopping sex mound and peeled her panties off of herself. "Oh, what a mess," she said as she tossed the now heavy garment aside playfully. She surprised me with her quick agility by her bold mounting of my face.

"Clean me up baby," demanded Vivian. I was in no position to argue and I licked her sweet sex folds and ridges. I grasped her thighs right at the area above her stockings and strained to drive my tongue into her sex passage, seeking more of her sweet juices. She tasted sweet and fruity as she swiveled her wide, well padded hips in lustful appreciation. She raised up when I sucked at her hooded clitoris. "Whoa, not there! It's much too sensitive." Satisfied with my efforts, she settled in beside me and slipped her hand down my torso, then under the tight, frilly waste band of my panties. I groaned as her hand slid over my spent cock. She rolled my balls around in her hands teasingly and murmured, "Yes, I do believe you're the best kind of girlfriend."