Youthful Fantasies

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Crossdressing

SESSION I

The recurring dream was disturbing, not because of its content, but because it reinforced my deepening sense that I was losing control. It was the same theme, and always involved a masked stranger who was sexually abusing me while I was tied to the bed. This morning I found the sheets stained, and my inner thighs were covered with a thin film of my vaginal secretions, while my pubic hair was slightly matted with cum juices. Somewhat embarrassed, I was relieved that my husband was out of town, and proceeded to strip the sheets, and get ready for work. I put on my gray flannel suit since the day was full of meetings with the State Educational Commissioner and other local administrators representing the county schools. I was the youngest high school principle among all attendants that day, and everyone seemed to agree that I was on a fast-track to success. Unable to keep the fantasy out of my mind, however, I did something that I had never done before. I left the house wearing black thigh highs, a lacy black bra and no underpants. I was sexually aroused.

After a long day of uneventful meetings, I went to the gym to complete my two-hour workout. Rather than shower there, I decided to go home and take a bath. Peeling off my clothes, I stopped in front of the full-length mirror, and became curiously aroused. At the age of 37, my feminine facial features and long brunette hair capped off a body that rivaled that of any girl in my high school. Since I never had children, by breasts remained rounded and firm, with nipples that were now decidedly erect. The curve of my breasts contrasted with the firmness of my abdomen, and my long muscular thighs rivaled those of any distant runner. The best part of my body was my ass which was now pinkly flushed from the exercise, riding high and protuberant on my model-like legs.

I got into the tub, and found my hands migrating to erect nipples, lightly pinching, followed by a more desperate need for fulfillment. I thought of my husband, but disappointedly admitted that he had been unwilling to satisfy the growing fire that emanated from my need for anal stimulation. My finger migrated to my clit, gently self-stimulating myself while I imagined the stranger in the mask. More relaxed, I reflected on the events of the last few months, frightened by my runaway emotions and sexual thoughts that fixated on the teenage seniors in my high school. I stroked myself more compulsively, fantasizing about their muscular bodies, firm erections, and sexual staying power. As my head spun, my body became progressively suffused with gentle warmth that gave some relief, but not the intense orgasm that I needed for completeness. I soaped my butthole, and gently inserted my middle finger, gradually, and then more deeply as waves of satisfaction began to mount. First, one finger, then two, deeper, deeper, as I rocked up and down in my activated state. My other hand reached for my clit, and I luxuriated in the intensity of the orgasm, shuddering as the ripples of my body were mirrored by parallel ripples in the bath water. As my orgasm abated, I once again cursed my husband for his disinterest in anal intercourse. I got out of the tub, put on my negligee and went to bed, feeling the sensual luxury of the satin rub against my nipples and wondering if the dream/nightmare would awaken me this evening.

I had no more dreams that week, although I was having a difficult time keeping my fingers from touching myself while I was behind my desk during individual student sessions. During the most recent experience, I caught myself putting my soaked finger into my mouth, tasting the sweetness of my love juices. Without even knowing it, I had almost started to stimulate my anus before I became acutely aware of the teenage boy in front of me. Frightened by the uncontrollable impulse during that counseling episode, I immediately cancelled all subsequent male counseling sessions. I couldn’t believe what was happening to me, and looked forward to the end of the year, hoping that the respite away from school and male youth would serve to resolve my impulsive behavior.

SESSION II

When the school year finally ended, I looked forward to the summer vacation. In the two weeks since school closure, I had no more sex dreams, and found myself returning to normalcy. My husband works away from home, and left that Monday morning for the week, leaving me alone until Friday night. It was a beautifully warm day, and I decided to enjoy the solitude of the backyard pool. Wearing my two-piece bikini, I jumped into the pool and did keçiören escort some laps prior to reclining in the mattressed lounge chair. As I fell asleep, I was awakened by the opening of the gate and arrival of the pool cleaning attendant.

“Excuse me, Ma’am. I’m here for the weekly vacuuming.”

What a surprise! Wearing a tight T-shirt and tighter shorts, tanned with thick black hair, this young stud was a real turn-on. I found myself staring, but recovered in time to respond.

“PPPlease, do come in,” I stammered.

As he started to connect the tubing to the skimmer outlets, I noticed that sweat was beading down his neck onto his shirt. Getting up, I offered to get him a glass of water which he willingly accepted. I thought I noticed him staring at me my erect nipples. Back to work, he continued to sweat, now with the perspiration soaking a larger patch of his T-shirt, but also the back of his shorts. In a very humbling and muted voice, he apologizingly said,

“Excuse me, Mrs. Philips, but would you mind if I took off my top?”

“Of course not,” I spurted out, as I watched him strip from the waist up.

He worked for the next 45 minutes, while I was fixated on the muscular biceps and pecs that moved back and forth in fluid motions while he completed the pool vacuuming. He clearly was a body builder, with rippled abdominal muscles that accented the rigid lines of his upper arms and torso. Turned on by the thought of sweat on muscles, I achingly thought of his moist buttocks and the tightness of his anus. The ache rose in my pelvis, as I felt my nipples stiffen against my bra, and my underwear start to moisten. With every back-and-forth movement of his arms, I imagined his rigid penis stroking my vagina, then my butthole, as I scrumptiously tried to satisfy my clitoral hunger by masturbating with a towel draped over my bikini bottom. With only minimal stimulation, I felt ready to explode, not experiencing intensity like this for years. As I was nearing orgasm, he disassembled the unit and prepared to leave.

“Well, it looks pretty good. I’ll see you next week.”

Rocked back to reality, I yelled.

“BBBye. What’s your name?”

“Tony. Tony Somelli.” And with that, he was gone. I jumped into the pool to try to cool my heated passions.

I masturbated every night that week fantasizing about Tony, having intense orgasms using just my fingers. It didn’t stop the sex dreams, however, which recurred even with my nocturnal fingerings and presumed sexual satisfaction. Anticipating my husband’s arrival on Friday, all I could think of was his cock inside of me. When he arrived home, I seduced him with a nice meal, new negligee, and a new perfume that I bought.

After dinner, we showered together, and I lathered his genitals before we went to bed. I took him in my mouth, first lipping the tip of his penis, then taking his entire shaft, so hungry for the taste of his semen. As I sucked his balls, he got harder, ready to explode. I then pulled back, turned him on his stomach, and licked his ass, slowly circling his anus until I probed it with the tip of my tongue. I had never done this before, but his heightened moans encouraged me to continue. My tongue entered his anus, tasting the bittersweet juices that were mixed with the soapy perfume remnants of the shower. As I continued to tongue his asshole, I started to stimulate my clit, both of us moaning and rocking in unison. I then took the fingers from my pussy, and inserted them into his lubricated anus, first one then both as he frenzied to a climax. Feeling his incipient orgasm, I kept my fingers in his butthole, but turned him on his back as my hungry mouth encircled his rock-hard penis. Never before was he so hard.

As I continued to fuck his anus with my fingers, his orgasm was mounting, mounting, mounting, until he exploded, shooting his hot cum juices into my mouth. I nearly came with him, as spurt after spurt of his ejaculate filled my mouth, overflowing to my chin, down my neck and onto my breasts. I hungrily swallowed most if it, leaving enough in my mouth so I could use it for my own self-stimulation. I rubbed it into my nipples, cunt, and asshole while it was still hot. I was so excited I couldn’t control myself any longer. As my husband massaged my nipples, I took my fingers from his asshole, and inserted them into me, rubbing his cum and asshole juices into my waiting asshole.

In out, In out, I couldn’t believe the sensation, as I lay on my tits with my ass in the air, fucking my asshole with his juices and three kızılay escort fingers. I needed his cock again, so I continued to finger fuck myself as I took his soft penis back into my mouth. Continuing to suck his member, I fantasized that it was Tony’s, and in a frenzy reached an orgasm as my vaginal muscles started to contract in unison with my anal sphincter. I screamed and shuddered all over, leaving my husband dazed at what he had just seen and experienced. That night, I never moved during sleep, and we both awoke to my husband’s rock hard morning erection.

SESSION III

As Tuesday approached, I could feel myself getting aroused at the thought of seeing Tony. Anticipating that I might need to relieve myself, I brought my glass dildo, vibrator, and lubricant. Tony appeared just likely before, politely letting himself into the pool area, and after initial greetings, started to work.

I couldn’t believe what a hunk he was as my sexual fantasies and lust started immediately. While I lay on the lounge watching him, I was trying to figure out how to discreetly masturbate myself. I had on a very tight bikini top that day with a thong bottom, and pleasingly noticed that Tony was eyeing me as he started his pool vacuuming motion. Just like last week, as he started to sweat, he asked to remove his top to which I hungrily agreed. What I said next surprised me.

“If you remove your top, I hope you don’t mind if I take off my bikini top.”

He hesitated, and uncomfortably said yes, looking away as he spoke.

Nervously, I undid my snap, and let my bra fall to the side of the lounge chair. He tried not to stare at my rounded breasts, but the bulge in his groin was already starting. Having gone this far, I anxiously asked if he would like a glass of water, and after hearing his acquiescence, I got up to give him a better view of my long legs and ass. I slowly walked with my back towards him, feeling his heat on my back. Returning with a glass of water, I noticed that he couldn’t take his eyes off my breasts. Furthermore, he was now rock-hard with a bulge that was mouth-watering, and needing of relief.

“Tony, if you don’t mind, could I ask you to lather my back with suntan oil?”

“Sure.”

He was over by my side in a heartbeat, and I handed him the oil as I turned on my stomach, giving him a bird’s eye view of my sensuous back and ass.

“Tony, have you ever been with a girl?”

“I have a girlfriend, but we’ve never gone all the way”.

“Tony, do you masturbate?”

Embarrassed, he said, “No.”

“I didn’t either at your age. You’re 17, right?”

“No, Ma’am, 18.”

“Tony, I was not sexually active until I got married at the age of 25. As a matter of fact, I didn’t start to masturbate until I was married for 3 years.” I didn’t tell him how I was feeling now, however.

“Please start to lather my back, so you can get back to work.”

With that, he started to gently rub the oil into my shoulders. His firm hands felt delicious as they kneaded my muscles, and it was clear that he had done this before. As he continued to work on my shoulders and back, he was drifting down to the small of my back. I could hear him breathing faster as his hands got closer to my ass. When he lightly touched my buttock, my breath quickened. I did nothing as he rubbed the oil into my buttocks, but felt my vagina soften up with moisture. As he continued to my thighs and inner thighs, my breath quickened, and I felt my butthole starting to hunger.

I turned on my back, and noticed the huge bulge in his pants. Irresistibly, I rubbed it through his shorts, causing him to moan in anticipation. Unable to wait any longer, I pulled down his shorts, exposing his 9-inch cock that was already bathed with his pre-cum. Aroused by the size of his erection, I grabbed the oil, and lathered his balls, still astounded by the size of him. I was dripping with love juices, and could feel my anal contractions. I started to stroke him, but he exploded immediately, shooting his hot cum onto my face, load after load after load, followed by more onto my tits. I giggled in joy at the amount of his ejaculate, bathing my face, chest, and abdomen with it. I then took him into my mouth, and sucked until he was completely dry, feeling the contractions of my vagina during my pre-orgasmic heat.

With my mouth on his member, he was hard again in a few minutes. I was more aroused, knowing that this time, he might last longer.

“Tony, I want you to suck my pussy.”

I took off my thong, spread my legs, and let ankara escort him go down on me. His tongue was like fire as he first kissed me gently, then with more urgency. As I stroked his cock, he sucked me with more need. I couldn’t believe it, but his labored breathing told me he was going to come again. Wanting to taste his seed, I changed our positions so that I could suck him while he licked me. His cock was huge in my mouth, and I could still taste his love juices from his first ejaculate. He stiffened, and I knew it was coming, quickly feeling the first long gush, followed by his second, third, and fourth.

Oh My God, it was wonderful as his cock stayed hard despite ejaculating into my mouth. His cum juices bathed my mouth and body for the second time, and I was dizzy with the feeling of taking this young stud’s cum into my mouth. He continued to suck my cunt as our collective heat remained unabated.

“Tony, I want you to suck my asshole.”

He was high on sex, and his hunger was directed to my asshole as I flipped onto my stomach, and put my ass up for his pleasure. My husband never did this to me, but here was Tony suddenly sticking his tongue onto my asshole. The sensation sent quivers up my spine, as he then expertly inserted his tongue, softening the opening, which then eased more and more, allowing his tongue deeper access into my butthole.

While he was tonguing me from the rear, I managed to find my glass dildo, and shoved it into my vagina, now fucking myself with the dildo while Tony tongued me from the rear. The intensity kept peaking, fueled by Tony’s raging third erection which could barely fit in my fist. In and out he went with his tongue, deeper and deeper, while I fucked myself with the dildo and stimulated my clit with another finger.

I knew this wouldn’t last long, as my orgasm peaked, my shudders starting deep in my stomach, then spreading outward to my muscles, lungs, and loins. My anal contractions were so intense that Tony’s tongue was getting periodically trapped by their intensity. With my explosion, Tony spewed forth his third ejaculate, load after load sending our bodies heaving together in our mutual orgasms. By this time, I was covered with his cum juices, which deliciously covered my hair, face, breasts, abdomen, and pelvis.

I couldn’t believe it, but I wanted more. I needed one more fuck, this time up my asshole. I needed Tony one more time.

“Tony, bend over.”

With that, I collected some of his cum from my tits, and rubbed it into the vibrator. Lubricated with his cum, I turned on the vibrator, and slowly started to stimulate his asshole. To my amazement and sheer delight, he was hard as a rock, pointing that 9-inch monster straight up to the sky, and leaving me drooling in glee. Without my saying anything, Tony then took the vibrator from me, and started the tantalizing process of stimulating my asshole just as I had done for him. I was a little intimidated by the size of that thing inside me, but Tony’s gentleness was overwhelming. Slowly, my asshole opened up, allowing him to put the vibrator in deeper until it was 6 inches deep. He was shuddering at the sight, and looked like he was going to explode again, as I was started to heave.

“Tony, turn on the vibrator.”

As it started to vibrate, coupled with the in and out motion, I could feel the sensations shaking my entire being. I wanted his cock so badly now.

“Tony, fuck me up the ass!”

I was able to take him only because the vibrator had loosened my sphincter so much. As he mounted me from the rear, by anus spread, first reluctantly, and then taking him whole. What a sensation as that huge cock humped me from the rear, riding me like a cowboy. I couldn’t believe he was in me, fucking me as my whole body quivered. Please don’t stop. Do this forever. It was my first assfuck, and I couldn’t believe the sensation as he mounted me. He lasted longer than I thought, finally shuddering with such intensity that our collective rigors shook the ground. We both heaved, groaning in unison, two as one, as we both experienced the most intense fucks of our lives. Even after we both came, my asshole contracted for 15 minutes, leaving his soft member inside me with no way to withdraw. As we both collapsed, and my sphincter relaxed, he finally was able to exit, leaving us both exhausted, but in spiritual bliss.

PROLOGUE

Tony and I had anal sex every Tuesday that summer, and I never saw him after that. My husband has allowed me to get a strap on, and he enjoys being taken from the rear once in a while. As for me, the sex dreams are gone, and I have fantastic orgasms now with vaginal stimulation as long as I am aroused with good porn videos. Every once in a while, I still fuck myself up the asshole using my vibrator or my fingers after my husband is asleep.

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