Driven To Desperation Ch. 04byfluidline1©
What was happening to me when Headless was not present during our sessions was beginning to alarm me. It was pretty much like what had happened when Ann wanted to make it in the car some time ago.
In the beginning, I would just close my eyes and think about either that big, black prick from Ann's magazine; later, I would conjure up the image of her straddling the portrait and working me up with her mouth. As the days went by, just images were not helping.
I visited Dr. Rao at the behest of my brother-in-law to whom I confided that I wasn't able to attain an erection any more.
My sister's husband was a year younger than me but by his own admission (and some feedback I received from Ann after her intimate talks with my sister) he was a sex maniac. More than once, Ann had revealed to me that my sister jokingly complained to her that Jai always seemed to be in a perpetual state of sexual excitement.
"I think you gotta see a shrink, Ash," Jai told me one day.
Dr. Rao was a thin bearded fellow, short and kind of weird looking. He began by telling me that it was more in the mind than in the body after conducting a series of physical check-ups, which cost me upward of three grand.
Of course, I never revealed about Headless to anyone. It was our secret and only Vera was the one outsider who knew about it.
"Do you or did you have any other sexual activities with anybody else but your wife?" he asked me one day.
I wasn't about to say yes, because that would involve revealing that I did have sexual relationships, or an extra marital affair, with another woman, namely Vera, in the presence of my wife. That would have shocked the hell out of the staid weirdo!
"Why?" I had counter questioned.
"Well, I wanted to know if you experienced the same thing with another woman as well."
That set me thinking. Would I feel the same way if I were making it with another woman? Would variety spice me up? I had been performing quite well with Vera; but that was when we were doing it with Ann and Headless. Could I keep up my performance with just Vera and no Ann or Headless around? Was Ann getting to be too familiar?
I didn't think so. Ann was definitely everyman's dream woman. I should know better because I had seen the various glances that she attracted from a variety of guys. Even the three blokes who worked for me in the office sometimes looked at her in a way that wasn't exactly platonic or brotherly.
I decided to try out for myself. I already had a couple of candidates whom I thought would be more than willing to get into my pants. One of course was Vera and the other was Meghana, my steno at the office. I could have had Vera all by myself very easily. But, I didn't as yet want to take a chance because I wasn't sure what Ann would feel like if she would come to know.
And come to know, she would. Vera wasn't that kind of a woman who would hold out secrets on Ann. Especially not after the affair we were having together. Meghana was different altogether.
Meg was a girl barely out of her teens; she was twenty to be exact. I had hired her upon Ann's insistence. Meg was the younger sister of one of Ann's friends.
I had noticed more than once the way Meg would look at me when she thought I wasn't aware of her. On more than a few occasions, she would approach my chair to ask for something which she would very well have asked either on the intercom or from behind the desk. During these times, she would get as close to me as possible; perhaps, brush her arms or breasts across my shoulders and lean down close to me. I had ignored all these come-on tactics mainly because I am crazily in love with Ann and I didn't want to create any problems between us.
But all that was past and gone. Now I had a new Ann. And a new problem.
I began to look at Meg in a different way. She was a nice girl; a bit too young for me. But what the hell! My wife too was when I had married her.
It was on a day that Ann planned to go to Vera's for the weekend that I planned my move. Making sure that I had a lot of work to finish (I really had), I told Ann I couldn't accompany her.
"Besides, you are going out for what I presume would be an all-girl party," I told her.
"I was thinking that maybe you and Headless also accompany," she had replied with a twinkle in her eyes. I almost succumbed.
I sent out the three guys for supervision at a remote site with enough work so they wouldn't return for at least a couple of days and I had requested Meg to come to the office earlier than usual.
For the first couple of hours, I really got down to work. I mean there was plenty of it pending what with Ann and Vera taking up most of my time for our crazy rendezvous along with Headless.
When we broke off for lunch, we headed to the room in Ann's office. We opened our lunch boxes and sat opposite each other on the table.
From time to time, I stole glances at her. She was wearing a knee length skirt that had a broad black belt at the waist. A dark red blouse that was tucked into it was tight enough to emphasize her curves.
She didn't have breasts the size of Ann or Vera's. Hers were pert though, and very, very firm. The blouse was thin enough for me to realize that she wasn't wearing a bra and flimsy enough for the material to sag down with the weight, revealing her cleavage whenever she bent.
It was amazing how much of a breast man I had become and I guess, that was since that day Ann had asked me to slide my prick between hers on that night we had oiled each other.
These days, I was obsessed with breasts.
"That's one hell of a dress you are wearing today, Meg," I casually remarked after we had finished our lunch and were seated on the table. I was smoking and pretended to be quite casual about my words.
"You like it?" she asked earnestly. "My mom says it's a bit too tight."
"Well, for a girl like you, that shouldn't be a problem. Tight dresses look good on girls like you."
She giggled. "And what kind of a girl am I?"
"You know. You are young and attractive. These kind of dresses emphasize that, huh?" I grinned.
"Emphasize what, Ash?" she looked at me mischievously.
I decided to go for broke. Boldly, I answered her question. "Why, Meg, I thought you knew. They emphasize your tits."
She blushed and was flustered. I guess she had never expected me to be so casual about it and so forthcoming.
She managed to smile at me. "You like them?"
"A guy would be crazy if he didn't." I replied, excited now that I could feel the faint stirring between my legs. Was it working, I thought?
She opened her mouth to say something, and hesitated.
"You wanted to ask me something?"
"W-well...I, huh, I just wanted to ask you if you'd really want to see them," she blurted.
I grinned at her, crushing the cigarette butt in the ashtray. "Why, Meg. Sure. Not only just see them, maybe I'd want to feel them, too."
She smiled suddenly, all traces of hesitation gone. She rose from the chair; "Lets just make sure no one disturbs us when you check these out."
She skipped out of the room. I knew she was going to lock the office.
I had an erection! Perhaps the knowledge that I was going to see Meg naked had spurned me on and set the blood pumping to my prick.
I pushed back the chair and spread my legs wide apart, partly to ease the pressure between my legs inside the jeans and partly because I wanted her to see the bulge there.
In fact, the bulge was so apparent that when she returned, her eyes widened at the sight of it. I saw her tongue flicking over her lips.
"Wow!" she breathed. Dumbly, she raised her hands, standing there barely a couple of feet away from me, and pulled down the straps of her blouse. Of course, she wasn't wearing a bra.
Her firm breasts sprang out. They were, as I said before, not as large as Ann's, just about medium, but boy, they were firm!
They didn't even move when she pulled her hands out of the strap so that the blouse lay over her back. Slowly, she walked to me.
"Okay?" she asked, striking a pose by resting her hands on her hips.
Casually I reached out and took both her breasts in my hands. I cupped them, testing their weight and feeling their softness.
"Great," I replied hoarsely.
Her eyes closed and a gasp escaped her lips when I squeezed them slowly.
"Hmmm...I like that," she murmured when I rubbed her nipples gently with the flat of my palms.
She threw her head back when I steadily began to knead her breasts.
She walked closer to me till my face was pressing against her belly just above the waistband of her skirt. She bent down slightly and immediately, I put my mouth over one breast, fondling the other.
"Oh god, Ash, suck it, oh god, yes, suck it like that."
This girl was one hot number, I guessed. I opened my mouth wide and slid in as much of her breast as I possibly could. I sucked hard on it.
I felt her hands fumble with my belt. She was so excited she couldn't unbuckle the belt.
I pushed her away and rose, rapidly unbuckling my belt and pushing down my jeans to the floor. Her eyes were riveted on the bulge in my shorts as I backed her against the table till she was half-lying on it.
I pressed against her and leaning over her body, I kissed her mouth, pushing my tongue between her lips.
She moaned as she began to suck on my tongue and gasped again when I now began to mash her breasts with my hands.
Her legs drifted apart and her skirt slid back to reveal her red panties. I slipped one hand down and cupped her crotch right over her panties and she moaned. She draped one arm around my shoulder and slid the other down over my shirt and right through the top of my shorts.
I groaned when I felt her hand wrap around my straining prick. I straightened myself, bringing her up along with me, still shoving my tongue in and out of her mouth. One hand pinching her nipple and the other rubbing her crotch, I glanced below to watch her hand sliding up and down my prick that was poking out from the top of my shorts.
She withdrew her hands and yanked my shorts down over my hips where they stayed around my knees. Now, she brought both her hands to my prick and jerked off the shaft with one fist and fondled my balls with the fingers of her other hand.
I was concentrating on keeping my prick erect. Triumphantly, I thought I wouldn't need too – her hands ensured that the shaft remained rigid.
I imitated her. I pulled her skirt up to her waist and then pushed her panties down. Once they were below her hips, all she had to do was wriggle her buttocks so that the panties lay in a puddle on the floor.
Then, I pushed her back so that she was lying half on the table and bent down, deciding to devote my attention to her young breasts. I sucked one, and then the other.
"Oh god, Ash, oh yes, lick my nipples, please lick them!"
I did. I first licked the erect nipple with the tip of my tongue feeling her writhing under me.
"Lick them, damn it!" she gasped, pushing her breast towards me.
I let the flat of my tongue rove all over the flesh. I felt her breast getting wet with my saliva and her nipple hardened even more than before.
"The other one," she begged and I repeated the whole procedure on her other breast while fondling and pinching the one I'd just licked.
When I covered her naked pussy with my palm, she shuddered. And, when I began to rub her pussy lips with my fingers she almost went crazy. The movement of her fist on my prick became faster and she was smothering the top of my head with kisses.
"Wait, please, wait," she said, pushing me away. Now what? I got an answer immediately as she knelt on the floor, her weight supported by her toes. Her head was below the level of the top of the table and I grunted aloud when she slipped my prick in her hot mouth.
My god! Up until now, I hadn't believed that little Meg would be able to do all these things. I mean there are many girls whom you believe wouldn't do things like sucking on a prick when you look at them. Meg was one such girl. Her innocent looking face belied such actions on her part.
But she sucked me with an expertise that was equal to Ann and Vera. She didn't waste time licking up the shaft; she straightaway slipped the length of my prick inside her mouth. Of course, she couldn't take the whole thing inside, but the three or so inches that she took, fitted her mouth well enough for her to begin bobbing her head up and down.
I reached down and massaged her breasts as she pushed my shorts down to the floor. She grabbed the back of my buttocks and pushed me closer towards her face. Gently, I began to move my hips to and fro.
Though she was kneeling down, her knees were still wide apart. I pushed one toe towards her pussy and heard her moan as I hit pay dirt. My toe encountered her wet pussy and I rubbed it over her protruding clit. She had a large clitoris and it was erect.
She pushed me away, now licking the wet shaft with little jabs of her tongue. "Mmmm, you taste so good, so salty, Ummmm, I love your cock, oh yes, mmmmm..."
So, she was a talker. I was surprised that this was the same Meg who had been sitting in my office for so long now. The demure Meg, whose cheek dimpled when she smiled.
She pushed my prick back against my belly and licked the underside; then, she was bending it down so she could run her tongue over the top.
I began to pinch her nipples and roll them between thumb and forefinger till she was squirming.
She rose suddenly and hopped onto the table. She put her arms around my shoulders and looking into my eyes, whispered, "Please, fuck me, Ash, give me your cock, I've been waiting for so long now."
I pushed her gently till she was lying on her back on the table. She immediately spread her legs apart and I glanced down to look at her pussy. The opening was wide and inviting.
I walked up to her and directed my prick into her opening. She moaned when I entered to the hilt and then clamped her legs around my waist as I began to move in and out of her.
"Oh yessss," she hissed, breathing through her open mouth. I seized the opportunity by bending down and planting my open mouth against hers. I could taste myself on her lips and in her mouth as I slid my tongue in. She sucked on my tongue.
Her pussy was tight, very tight. I recalled the first time I had put my prick in Ann. Meg was tighter more than Ann was when I had popped my wife's cherry. And Meg was no virgin.
My shaft felt like it was gripped in a vice and I thought I would burst. So, I slowed down. And, that's where I think I made the mistake.
All of a sudden, I felt my shaft going slack. Not to a very great degree, but it wasn't as hard as it had been moments ago. Desperately, I shoved hard into her, as if the act itself might help my shaft regain it's original hardness, but no, it slowly began to soften.
I pulled my lips away from hers and suddenly stuck a couple of my fingers inside her mouth. She began to suck them earnestly. I noticed that she had closed her eyes and her nostrils were flared.
That helped a bit. I mean the sight of her sucking my fingers was helping me, though not much.
Suddenly, I had an inspiration. Bending down over her so that her face was buried in my chest, I fumbled for the side table where I had kept a magazine.
She didn't realize it (and never did) when I frantically opened the glossy.
The picture instantly brought the blood racing back to my shaft and this time I began to move inside her so fast, she whimpered.
She began to move back against me, still sucking my fingers. She matched me stroke for stroke.
It was only after she suddenly went rigid, pulled my fingers out of her mouth and started to wail, that I hastily stuffed the magazine back into the side table.
I pulled out my prick when I came, letting my semen spray over her belly. I clutched her breasts and she jerked my shaft furiously till I was empty.
"Oh god," she breathed, her chest heaving, "that was great!"
What she didn't know was what I had to do to make it great. I realized that I was hooked.
The picture that had helped me was of a big-breasted brunette taking on a bunch of guys on a sailboat. One guy was behind her, his shaft inside her pussy, another was in front of her, his dick inside her mouth and she was holding on to two other shafts by her hands.
I was lost! I had become a weirdo.
Ann and me were sharing Headless every time that we wanted to make it. I suppose she was as addicted to that dildo as I was. And that was why I decided to question her about it.
We had just finished a marathon with Headless that night and were lying on the bed, Headless resting against the wall.
"Can I ask you a question, Ann?"
"You already are," she giggled, curling up to me, throwing one naked leg over my hips. She pressed her breasts against my arms and casually took my flaccid prick in her hand.
"What is it that you really like about Headless?" I blurted out.
She caressed my prick and thought about it. Ann was always like that. She never answered any questions instinctively. She needed space, and time.
"Above every thing, I adore his cock!" she laughed.
She never addressed the portrait as "it". It was always "him" just as the dildo was always "cock".
"That fucker doesn't have a life!" I joked.
"As long as I have this live one," here, she tugged at my prick, "do I really need that to be a live one?"
I hesitated a bit, and then blurted out, "Do you at any times fantasize that Headless is a real guy?"
Her hand on my prick sort of froze and I held my breath wondering if I had gone too far.
Finally, she answered, "Do you?"
I managed to laugh. "Look, Ann, I don't require a prick. I'm happy with your pussy."
"I mean, does that cock not give you a charge? Like, I know that the sight of me working on that cock really gets you all charged up."
"You are avoiding my question," I protested.
"I will answer that if you answer mine."
I paused. "Okay, fair enough, Ann. Yes. It kind of turns me on when I see you stuffing that cock up your pussy when you are playing around with mine. For that matter, I go wild when I see Vera and you making it out when I am around."
"Well," she said after thinking for some time. "I admit that very often I do fantasize about Headless having a real life cock."
"And," I asked, my heart hammering wildly now, and feeling my prick twitching in her hand, "whose cock do you, think is it?"
This time she didn't hesitate. Manipulating herself so that she was lying half on top of me, she wrapped a fist around my prick, pressing her ample breasts against my chest.
"I know who you had in mind when you did Headless."
I felt a chill run up my spine. "Y-you do?" I stammered.
Her hair surrounded my face as she lowered her lips and fastened her mouth on mine. I put my arms around her, pressing her closer to me (if that was possible) loving the feel of her breasts against my naked chest.
She pulled back and looked at me from under her lashes for a long time, a mischievous smile playing on her lips.
She leaned down again and put her mouth close to my ears.
She told me who she knew that Headless was when I did him.
And she was right! I hadn't realized that it was so apparent. Or, that I was such a damn good painter.
My sister's name is Raveena. She is five years younger than me. A long time ago, when she was about twenty, she fell for a stupid mutt head. A year after she had begun to see him (she was doing her arts then) he dumped her. Knowing her as I do, I was (and still am) pretty sure that she did not go too far with that bloke; maybe a few kisses, a few innocent gropes.
Our parents had to relocate to another hick city for Dad to complete one of his projects there. I stayed back, still doing my graduation. She had to accompany them to that hick city. When she was there, a brother of her close friend she had made in the city fell for her; hook, line and sinker. She was fortunate, because she ended up marrying him.