A Game of Consequences Ch. 09
Chapter 9. Sneaking in from Behind
Colin Dawson wasn't how I expected him to be. I'd been observing this guy with a small suitcase at the train station cafe, then Jill showed up, looking scrumptious in a t-shirt, tight jeans, and trainers. I thought she might shove him onto the tracks, but instead, he leaned in for a kiss.
Tall and a bit stocky, he had a head full of dark, curly hair. He wasn't what I'd consider handsome, but what did I know about the men women find attractive? I'd hoped he would be an ugly brute, a man unfit for the lady I'd convinced myself I was in love with back in Rome - but he wasn't. He was a presentable, fit guy who wasn't bad-looking and seemed genuinely attached to Jill.
His train arrived, and he spent time kissing his wife before getting on board. After the train left, Jill stayed on the platform for a brief moment, seemingly deep in thought. Then, she turned and walked away, glancing in my direction and nodding slightly without stopping. I got up and followed. I figured that, on a Sunday evening, it wasn't impossible for someone who knew her - a student, a parent, a neighbor - to be out and about or meeting someone, so it was best if we didn't appear together.
Upon leaving the ticket hall, I could see Jill heading to the car park, so I did as well. When she reached her car, she opened the back passenger door and slipped inside the driver's seat. I took the hint and hopped in the back, dropping my bag on the floor next to me.
"I didn't want us to be seen together..." she explained.
"I understand. But why the back seat?"
"When we get to my house, I need you to lie down. I don't want the neighbors to see me bringing a guy home just after dropping my husband off at the station. I'll park the car straight in the garage, and you can get out when we're out of sight."
The garage had a door that led into the kitchen. Jill headed to the fridge and poured two glasses of white wine, handing one to me and taking a generous gulp of her own.
"You know, I almost canceled this meeting. Apparently, my husband's infidelity is supposedly over. And here I am, getting my revenge. But it's not truly that. Ultimately, I just gave goodbye to the man I intend to start a new life with in Edinburgh in a few weeks, and then nonchalantly brought home a boy who anticipates banging me silly for the next 36 hours or so. Can you understand why I'm feeling a little unsettled?"
"Certainly, but I can help you feel better. Much better, actually. Because I'm not merely a boy, partly thanks to you." I moved in and kissed her. After a bit when I felt her body tense, she relaxed in my arms and reciprocated the kiss with affection. Eventually, we pulled apart.
"You understand this will mark the end of it, right? On Tuesday, if we ever cross paths again, we'll be nothing more than pupil and former teacher. Nothing else but that?"
I signed. "Yes, Jill, I get it. But for now - let's forget about that. We're immersed in our desires and needs, separated from the outside world. Here and now is where we are."
I kissed her again and started hooking her t-shirt off.
"Hold up, big guy." she added. "We have thirty-six hours, if not more, by which time I'm expecting to be exhausted and possibly worn out. Let's not be in a hurry. I'm going to shower, and I suggest you do the same. Finish your wine first."
The bedroom was quite spacious, as I wasn't used to such large living quarters. The bed was bigger than a typical double, and the fancy-looking furniture appeared to be of high-end quality. I noticed there was a full-length mirror that could be used to see oneself while in bed. I imagined this mirror was used for more than just checking one's clothing before leaving the house. I put my bag on the bedside table and placed my glass on the bedside cupboard before heading back downstairs to the bathroom.
After my shower, I wrapped a towel around myself and proceeded back to the bedroom. Jill was standing in front of the mirror, completely naked.
"How do you like what you see?" she asked while not turning around.
I approached her and wrapped my arms around her shoulders, before planting a gentle kiss on the back of her neck. "You look stunning," I replied.
"For an old lady?"
"Stunning for a woman, no matter her age." I leaned in and planted a kiss on her lips. The towel dropped from around my waist, exposing my hardened penis, which pressed against her backside.
"Interested in me?" she inquired.
"Definitely," I responded.
"I can feel it," she said while turning her head to face me and kissing me again.
We studied our reflections in the mirror. "Yes, we do look good together," she concluded.
"Hot and sexy together," I added. I trailed my hands down her arms, across her flat stomach, and up to her full breasts. My traced hands encircled her bust, tweaking her nipples between my fingers. Meanwhile, she wrapped her hand around my erection and massaged it from base to tip. I lingered near her delicate neck, leaving a trail of kisses across her shoulder and up her arm. Once satisfied, I carefully pulled away from her grip and sunk to my knees on the plush carpet below. I traced my tongue across her thighs and downstairs to her backside, where one hand caressed her enticing ass cheeks while the other probed between them.
She giggled as I tickled her soft, pink starfish. I remained on my knees before us, admiring her perfect form while caressing her body with the utmost care. Jill panted, "Stand up."
I removed my hand from her vagina and cautiously rose back to my feet. By this point, I released my cock and allowed it to rub against her pussy without an intermediary barrier.
"Enter me," she whispered, her breathing speeding up. Her body shook with anticipation.
"Aren't you worried about catching something?"
"I'm on the pill. I want you to cum inside me. Please," she pleaded.
I was eighteen and despite the schooling provided by Jill and Phoebe, I had quite an active sex life. While I was fairly confident in my sexual abilities and my partner's health, I wasn't familiar with having sex without a condom. We were both knowledgeable about sexually transmitted diseases at the time, and it was generally a fearsome thing. However, I felt I could trust Jill and, in a moment of recklessness, decided to forgo the rubber.
I spread my legs widely to ensure my crotch was at the right height and positioned my cock to enter her vagina. I grasped it, guiding it to her entrance. My erection pressed inside of her, and she issued a guttural groan. While maintaining firm contact with the front wall of her vagina, I mentally recited a list of kings and queens, using it to help keep myself from orgasming prematurely. At this point, I was eighteen, and I'd never fucked one of these free-flowing lubricious (and sexy!) cunts before.
"Jilly, sex without protection, this time," I announced after a few seconds.
"Ah, so you're interested," she noted, accentuating the word "interested" with a naughty smile.
We weren't kids, and the fear of diseases was prevalent. However, I trusted her, I assumed she was as cautious as I, and I wanted to know what it felt like to feel my naked cock inside a woman's pussy.
"Hold on," I said as I stood, allowing my cock to rub against her vagina. I gripped it, making it even more sensual.
"Richard, look at me," Jill said breathlessly.
I glanced into the mirror where our reflections projected a wild and intimate scene of passion. In the reflection, I could see Jill's beautiful face, her eyes half-closed, her legs spread.
Enjoy it. If you - if you finish - you can - you can end me with - with your mouth and - with your fingers. Just - just fuck me - fuck me hard." She was breathing heavily.
I tried; I really did. I even started to recall the consorts of the English monarchs. I started with Matilda of Flanders, Queen Consort to William I and managed to get as far as Isabella of Valois, Richard II's second wife, before Jill's hot, silky, juicy cunt, the sight of her delectable body in the mirror, and her moans of "Oh yes. Oh, fuck me harder!" pushed me over the edge.
There is honestly no comparison between coming inside rubber and squirting your semen into a wet, welcoming womanhole. Before my first bareback fuck with Jill, I'd enjoyed the wetness of a few female mouths, including unloading into Phoebe's, Jill's, and Sharon's - and, albeit much too quickly, into Kathy Barber's. Now, firing into a girl's mouth is a thousand times better than coming into rubber. But my first experience of feeling the fantastic release of coming inside Jill's juicy fuck-hole was deliriously joyful. I think I must've moaned loud enough to have been heard by the neighbors if Jill hadn't thoughtfully closed the bedroom windows earlier.
I kept thrusting for as long as I naturally could while frantically rubbing her clit. I even moved my hand around from her tit, moistened a fingertip with the abundant juices that we'd produced, and inserted it into her puckered asshole, up to the second knuckle. But, by then, my erection was rapidly deflating, and she still hadn't reached her climax. When my cock finally slipped out, she turned to me and said, "Finish me. On the bed."
After another minute, with her legs spread wide, a finger embedded deeply in each of her holes, and my mouth focused on her clit, she was bucking and squealing as I felt her coming. And a few minutes later, we were lying side by side on her bed, casually sipping the remains of our rather warm wine. It tasted odd, mixed with the flavour of Jill's juices and my semen.
"I hope you didn't mind coming inside me like that. It's a bit messy, but having semen trickle out of me afterwards makes me feel horny again."
"Mind? It was amazing. That's the first time I've been inside a girl - a woman - without a condom. I'm sorry I lost control."
"That's OK; it's what I expected. And the mouth-work afterwards was excellent. Thank you, Richard. Now, I know you've eaten, but I need to get us something more substantial if we're to have the energy to try again. Pasta?"
In the dining room, she produced two bowls of tortellini with a mushroom sauce. We sat and started eating. She'd pulled on a short robe that looked very sexy on her. I was just in my underpants.
"This is good. You put it together really quickly."
"I didn't; Waitrose did. You just heat it up in a couple of minutes. I'm not intending to offer Michelin-starred catering, you know. I might offer some Michelin-starred fucking later."
"I wasn't expecting culinary delights. I was expecting to use my mouth for other purposes. I'm hoping you might do likewise."
"Possibly." She gave me a 'naughty' smile, but then her expression changed. "You know, I nearly called this whole weekend off," she said, putting down her glass and giving me a rather sad look.
"What? But we..."
She put a finger to my lips. "Look, Richard, I'm a married woman. Having sex with you is exciting and fun, but I have to be practical. A divorce right now would be a major disaster for me. I thought that my marriage was back on an even keel, and the move to Edinburgh would be a fresh start for Colin and me."
"But?"
"But when I came home on Tuesday, Colin was on the phone. He saw me and said, 'Sorry, Mike, gotta go. Jill's home and I need to cook dinner. See you around.' Well, I thought nothing more of it. Over dinner, I asked what Mike had wanted, and Colin said his friend had called to see if we wanted to go for a pub meal on Sunday evening. Colin said he'd explained that he was off to Edinburgh and we couldn't. I thought no more about it, except - except on Tuesday, Penny, Mike's wife, turned up in the school office with a sports bag that their daughter Lynette had forgotten. She's in the First Year, in Mr. Gould's class. We said hello and, in passing, Penny said how she was being run ragged by the kids because Mike was away on business in Zurich and wouldn't be back until next Wednesday. That's when I realised that Colin was lying again, and I finally decided that this little adventure was back on."
"What about Edinburgh?"
"I hope the call was him ending things with his mistress. It'll be tough for him to maintain a physical connection when his target remains four hundred miles distant. I'll keep an eye on the situation in the coming months. But what's in store for you, slender Mr. Watson?"
"I met a girl in Oxford. She's expected to attend the same college, assuming we both pass our exams."
"And by 'met,' you mean you..."
"Well, we swapped bodily fluids."
"I hope it was with a condom, or I may have to reconsider offering my naked pussy."
"Of course. Yours was the first I've encountered without protection. We downed quite a few beverages."
"So you're implying it wasn't just a one-nighter?"
"No. I'm planning a visit to her abode next weekend. We've been communicating."
Jill smiled. "That's fantastic! I would've been let down if you'd chosen celibacy. What a waste, given all I've taught you. I'll need to evaluate what you've learned and impart more instruction before this expedition comes to a close. I'm looking forward to round two soon. Finish changing into your school attire. I'll deposit these dishes in the kitchen and rejoin you back here shortly."
I paid a visit to the restroom to clean Jill's juices off my face and my equipment then applied a bit of cologne. I then donned my uniform, omitting underwear, combed my hair and made my way downstairs. Upon the dining room table lay a notepad and a pen. On the top sheet, Jill had written 'Detention job: pen 100 times "I must not say 'fuck' in class."'
I commenced. The first two lines mirrored Jill's orders, but subsequently, I swerved from her instructions. When she reappeared, she was donning an old-fashioned teacher's robe over her gown. During my early days in the Grammar school, a few old-timers continued to sport them, supposedly to minimize the amount of chalk dust on their clothing. By the time I had enrolled in the Sixth Form, they had become outdated and no longer necessary with the transition to whiteboards and pens. I noticed she was wearing tights - or more likely, stockings - and the heels she had on were inappropriate for a day in the classroom.
She perused the lines I had penned. They resembled:
*I must not say 'fuck' in class.
*I must not say 'fuck' in class.
*I must not fuck in class
*I really must not fuck in class
*I really desire to fuck in class
*I really desire to fuck Mrs. Dawson over her desk
"Richard," she chastised in a scornful voice, "I placed you in detention to instill a lesson. It appears you're resistant to learning. I'm compelled to escalate the penalty. Stand up. Now bend over and place your hands on the table."
As soon as I did so, she slapped my behind. It wasn't particularly hard or painful, so I remained still. She did it again. And again.
"It seems I'm not yet sowing enough discomfort. Very well, Mr. Watson, you leave me no alternative. Undo and lower your trousers."
"What, Miss?"
"Unfasten them and pull them down to your knees."
"But Miss..."
"Obey, Richard."
I gradually unfastened and unzipped my trousers and lowered them as requested. Then, I lifted my shirt, exposing my bare arse that was awaiting the spanking that seemed imminent. My cock was already mostly stiff.
She spanked me, again not very hard. I wasn't particularly keen on BDSM - or at that time, I wasn't, and I still don't enjoy inflicting or receiving severe pain - so while it was thrilling to have Jill slap my buttocks, it didn't provide any particular pleasure. However, she then said, "What's this, Mr. Watson?" and she gripped my cock.
"What is it, Miss? You've encountered one before, Miss. I'm sure you've copulated with more than one - OUCH!"
She spanked me again, this time a bit harder, but she also began stroking my cock. It was just as my fantasies had suggested.
"It's not my concern how many cocks you've held or fucked, Richard. The fact is I now possess your cock, and it's hard. How do you explain this?" She slapped me again.
"Ouch! Well, Miss, you're lustful and alluring, and you're pleasuring my cock. Of course I'm hard. But you're playing with fire, Miss."
"In what way?" She slapped me again, but this time it hurt a bit more. However, her adept hand-job overshadowed any discomfort I may have experienced. Nice work!
If you keep pushing the boundaries like this, Ms. (Insert Name), you might just find yourself getting fucked.
"Tell me more about that," she replied with a raised eyebrow, still holding my cock. I was the one that initiated kissing her, reaching my hand up to pull at the opening of her robe. To my surprise, her dress was oddly revealing. It was black, short right above the knees, strapless, and unzipped from the bottom, with a large metallic ring appropriately placed on the zipper's tag. I tugged on the ring downward, which unclasped with a loud noise.
What appeared before me was none other than the sexy, fit girl I've done so intimately before - Jill. In that moment, she popped out of the dress and let it fall onto the floor. The ensemble under was more revealing than most lingerie; a simple black bra which had disappeared long ago, stockings topped with suspenders, and tiny transparent panties with suspender straps. Quite a show stopper, seeing her half-naked.
"What's the plan, Mr. Watson?" she asked, a suspicious tone in her voice.
"I'd like us both to get ready for a little session," I replied, my face filled with mischief.
"You think I'm gonna fuck you without permission? Will you rape me?"
"Unlikely without your consent. Though, perhaps you'll give it anyway after this." I grabbed her waist, dragging her towards me. My lips locked with hers as I reached for the double knots of her panties. Swiftly, I pulled the straps above her shoulders, freeing her of the ties. In one swift motion, I hoisted her onto the table, her legs spread apart, still within her stockings.
And then, I was on my knees, just inches away from Jill's pussy. I clamped one hand on each of her stockinged leg, settling between them for easier access. The first thing to make contact with her body were my lips, drawing long strokes along her inner thigh, hearing her sigh ever so slightly. Through all of this, Jill's hands remained occupied, clutching tightly onto the back of my head.
"Mr. Watson, can you possibly undress without increasing the intensity of this?" she asked, tone brimming with both reproach and eagerness. I thought quickly as to how to address this while not breaking the moment. It wasn't difficult since I only needed to unbutton my blazer and pull aside my shirt sleeves.
That done, I returned to her glorious pussy, delving my tongue deeper into her now-yearning entrance. To match it, both of my hands wove between her legs, cupping her thighs, and pulled her back onto my face. I received only rewards in the form of a crescendo of moans and proper cursing.
While Jill remained oblivious, I distractedly fumbled with my necktie. Soon, I vaguely remember throwing everything onto the floor and getting ready to get it on with the view of the woman above me. However, Jill underestimated my need to feed on her juicy snatch. She pinned my head in place but still insisted on crowning me with her pussy, holding my face tightly to the cloth. I pushed through her grip, yanking off my necktie rather forcefully, and a collection of materials soon piled behind me.
Moments later, Jill was shouting for more, her hands still clenched to my head. We paused momentarily as I removed the last of my clothes, focusing my attention to making her cum with both hands and mouth. I savored the taste of her arousal, provided freely to me.
"Oooh my gosh! Faster!" she cried. I scattered between playing with one hole and the other using my tongue and hands, then took a break to lift her to my mouth, her legs spread, heels scratching my ankles. I took a moment to savor the stockings and her amazing legs. I guided myself suddenly, lining myself up with her hips as she grabbed me by the ass and lifted her back, pulling me in. Panties were lost without a trace.
Mere seconds later, my cock penetrated her. Upon hearing her shriek, "Oh Richard!" I slowed down ever so slightly. After a few strokes, she clamped onto my hips, signaling her desire to have me push deeper, over and again. Jill gave me the impression that she wanted me to stroke more forcefully and that she was having the best time of her life.
And then, I noticed the strange sensations between my thighs rubbed by her stockings. When I turned to take a second look, she pulled my hips further in, positioning me perfectly. I briefly struggled out of my pants before the sensations vanished, and I focused on our coming fuck. I saw Jill's eyes widen, her eyebrows raise, and her hands clutch tighter on my hips as she asked for more.
After I'd established what my hand was doing, I went back to her vagina, licking and fingering her g-spot and clit. Her panting grew louder, more frequent.
"Harder!" it seemed she was ordering me, "OH GOD YES! OHFUCKOHFUCKOHFUCK! Deeper in the back!"
So I did just that. I pushed deeper, still intent on giving her more than what she wanted. And soon, she answered. An ending groan, a series of "Uhhuh," and "Oh!" and a shaking from her thighs - she'd climaxed. I stayed for a couple more strokes before letting go.
I didn't stop there, though. Instead, I continued my thrusts, each one more powerful and more lustful than the last. She moaned, gasped, and wriggled, impaled on my hard flesh. And she kept coming. I could tell we'd both had enough, so I gave into the pleasure and surrendered to a series of long, joyous spurts that finally brought this ecstatic lovemaking, it truly felt like that's what it was, to a Mutual Climax. Our lips met, and we panted and gasped into each other's mouths, holding on with arms and legs, enveloping and invading, her tight cunt muscles gripping my fading cock, milking out the last of my juices.
We were completely drained. We kissed and caressed for a while before I moved to remove her minimal clothing. We both collapsed onto the sofa.
"It was... interesting," she remarked finally. "You lasted longer than expected."
"I lasted longer than expected, too," I replied. "You were amazing."
"I've been told that," she teased. "By the young man who feasted on my pussy and got me to the brink of orgasm. You've become quite a lover, Mr Watson."
"Thank you, ma'am. And you're spectacular. Shall we go to bed?"
"Not quite yet. Colin will be calling around 10, once he's checked into his hotel, and I have to maintain normality. Get us more wine; it's in the fridge. I'm going to turn on the TV so I can lie about what I've been watching."
A few minutes later, the phone rang. I exited the room, not wanting to embarrass Jill with her lies to her husband or to be reminded that, after this final performance, he'd be the only one to have access to her alluring body. I climbed the stairs, cleaned my teeth and washed the sweat and sex juices off myself. She joined me in bed soon after. I didn't inquire about the call, nor did she reveal any information regarding it. We held each other until we both drifted off to sleep.
The next morning, I awoke to the sound of Jill's voice from the lounge. She was phoning the school to say she was unwell and couldn't attend. I ventured downstairs. Jill was wearing the same robe from the previous night and looked every bit as beautiful.
"Do you want breakfast or sex?" I inquired after she hung up.
"Om nom nom. Breakfast first. We have a lot of sex planned, and I'd like to avoid having it on an empty stomach."
After cereal, fruit, toast, and coffee, she inquired, "Are you satisfied with the amount you've consumed?"
"Yes, thank you. What's next?"
"We discussed certain activities in Rome. I'd like to engage in those."
"I can't believe this is happening. Jill, let's take it slowly."
She untied her robe, revealing the plug behind her buttocks. The three-centimeter rubber bar was set across her anus.
"Holy moly, Jill! I didn't think... Jesus! It's stunning!"
"Here's where we need to be careful," she cautioned. "I've tried it, with a plug and vibrator, and it's OK. I managed to make it painless and even slightly enjoyable. I might need you to cease if it's painful. If it doesn't feel good, I want you to come straight away. But if it feels good, you'll need to continue until I climax. Think you can handle it?"
"I'll do what you want, Jill. I promise you."
She removed her robe and tossed it aside. From its pocket, she procured a tube of lubricant and a few condoms, placing them on the table. I stood up, removed my intoxicating underpants, and positioned myself close to her. Our lips met and our hands explored. Fingers caressed her nipples while I teased her inner thighs before becoming more aggressive by fingering her soaking wet and immensely desirable folds. I started alternating between rubbing her clitoris and finger-fucking her exquisite cunt, and she was clearly just as aroused by the prospect of what we were about to do.
"It's time," she said a few minutes later.
She turned around, bent over the table, and exposed herself. "Carefully insert the plug. Take it slowly."
I gently tugged out the rubber anal plug. Jill gasped.
"OK?" I asked, worried.
"Yes... It feels... Weird, but sort of... Good/Bad. I don't know. Pull it back in a bit. I need it to stretch me."
I did as instructed. Jill tensed, but then the plug popped back out.
"Stop! Don't remove it entirely. Push it back a bit then pull it back again. It needs to loosen me up."
I was gently inserting and withdrawing a plug when my partner handed me an opened tube of lubricant.
"Take it out and instead, put a lot of this on your fingers. Then put one finger into my ass."
I did as she instructed. "Good. Deeper. Yes. Now, in and out. Mmm. That feels good. Now, a second one. Ouch! Be careful with your nails. Just stretch the ring. Yes, that's good. In and out. Try to spread them apart. Now - now see if you can get a third one in. Ah! Ah! Ooh, that's quite a stretch. Be gentle. Slow. Push deeper. AH! Oh, damn, that's... OOH!"
"Is it hurting?" I asked, concerned that I might be doing something wrong.
"No, not exactly hurting, but a strange mixture of not-quite-pain and odd pleasure. So..." She handed me a condom, with the wrapper removed. "Can you get that on with one hand?"
It would've been easier to stand on my head and sing Rule Britannia if offered the chance to fuck my partner's ass.
Thoroughly coated in lubricant, she spread some on the head of my rock-hard dick with her hands. "Spread that around," she ordered, and I did. Then she doused the rest of my thick cock in the sauce, making it as greasy as a transport cafeĢ sausage. Meanwhile, my fingers were dilating her tight hole.
"Alright, Richard, here's our plan. Your fingers will exit my ass, your cock's head will move into place immediately, and the second you push, you must hold back. Don't go too deep too soon. Allow me to guide you. And if I say 'STOP', you immediately stop. Don't pull out unless I tell you to, just stop where you are and await more instructions."
My fingers withdrew, the head of my cock touched her sphincter and slid in very gently into a hole that seemed much smaller than when I had first removed the plug.
"OK, Richard, push now."
I pushed, and was met with her gasps and muffled murmurs as I applied increasing pressure, yet still felt I was barely making progress. Then my dick suddenly popped up in the cleft of her ass. I grabbed it, pressed it into place against the indentation of her tight ring, and pushed harder. Her body tensed, a series of grunted "Nnnn! Nnnn!" moans emerged as she pushed against me, and then a scream as I fully entered her. The head of my cock slid inside her ass, and she cried "STOP!"
I ceased advancing, feeling the head of my cock and about an inch of my shaft gripped within her super-tight ass. It was almost enough to cause me to climax on the spot. I'd managed to fuck my teacher's ass with my cock! How freaking cool was that?
I was aware of her panting and her murmurs, until she steadied herself and said "Watch my clit! Don't use the hand that's been in my ass. Yes. Give my pussy some attention while I try to relax. Fuck, Richard, your cock feels large in my ass."
And at that moment, I started mentally reciting the sequence of monarchs, thinking, "I'm fuckin' Jill's ass, ma'am!" I had almost reached the sexual jackpot. Plus, her super tight rectum was squeezing my cock like a fist.
But her grip loosened slowly, gradually. And I didn't need to thrust, as she slowly, lazily, pushed back against me.
"Go slowly. Just a bit deeper. Yes, yes that's - that's good. Now, pull back just a bit. OOOOH! Yes. Rock your hips. Oh yes. Like that. That pull on - OH! Yes, on my ring, that's - fuck that's hot."
"Of course it's hot. I'm fucking your ass, Mrs." I panted into her ear.
"WHAT? Richard, what do you mean?" She pushed backward, allowing maybe half my length to enter, then withdrew it so that my cock-head again teased the inner rim of her tight ring.
I made sure that my fingers were stroking her clit before I responded, "I'm fucking you in the ass, Miss. I'm pounding it right up there."
As she pushed back, I increased my pace, deepening my thrusts into the tight passage. She let out a scream of delight.
"Oh my God, Richard! Your cock is so deep in my ass. So... Oh my God, that's deep!"
Her ass met my stomach as I crept all the way in, and suddenly, six inches of young cock were buried deep in her virgin rectum. She was in shock from the sudden penetration, but when I pulled out slightly, tugging at her ring, and then slid back in, there was no denying our connection. I felt slick and sincere pressure down low, and there was no release in sight.
I quickened the tempo while consistently rubbing her clit. The young woman was panting, barely coherent. She was moving her hips to meet each of my thrusts, pressing her pussy into my hand. I held back from going harder, choosing instead to speed up my hand movements instead.
Leaning in, I asked, "Where's my cock, Miss?"
"It's in my ass," she answered, gasping for breath.
"No, Miss, it's way up your ass." With that, I powered through, pushing in hard for maximum penetration.
She let out a series of "AAAAAAAH" sounds that were half surprise and half pleasure. I pulled back and repeated the motion, trying meticulously to avoid slipping out of her asshole.
"What are you doing, Miss?"
"You're... you're fucking my ass. You're fucking my... OH MY GOD, MY ASS..."
She let out a series of high-pitched squeals that were a mix of pleasure and pain. I began tapping her ass, inches from her vagina. Then her legs started to tremble, and the pulsing in her ass was pronounced, like she was contracting rhythmically to milk my cock. The sensations were out of this world, as I couldn't believe how intense they could be. I had no choice but to give in to the pleasure, firing my semen into the condom.
In summary, we both came in a heated fit of intensity. The pulsing throughout my cock reverberated throughout my body, resulting in powerful moans. It was just fantastic.
"Stop. Please, please stop!" she begged for a moment and then reminded me why. I was still stimulating her clit. I moved in, circling her neck with my arms. She turned, expecting a kiss, and I delivered.
We lay there, basking in each other's presence, until my semen-soaked cock slipped out of her. When she made it back to the bedroom, I'd unexpectedly prepared a cup of proper coffee. She was again wearing the robe from earlier and looked sexy and vulnerable.
She looked up at me, cockily, "How was that for you?" she said, taking the coffee I offered.
.". gushing "Amazing. With what you and I have experienced, it's hard to imagine a more mind-blowing experience. But what matters most is your pleasure." I took a sip of coffee, trying to look at her sincerely.
"That was incredible," she said, taking another giant sip.
I sipped mine and then raised it to my lips once again. Her robe caught so much attention. I was still amazed that we had reached the heights of our sexual bond with an attack on her posterior.
"How was it for you?" was my response.
"It was," she said, "But now I need to go to the bathroom." She stopped me and asked, "Make us some coffee." Then she left for the bathroom, a little tremble in her step.
When she returned, I'd made us a cafetiere of coffee a half an hour before. She was back in the same robe, looking confident and radiant.
"How was it for you?" was her question as I passed her her coffee.
"Magnificent," I replied, gazing intently into her eyes.
It was amazing, but also unexpected. Colin had asked for anal multiple times before, and I always refused. He's bigger than you, and the thought of that large cock doing what I had just done to me was too frightening to consider. However, after Rome, I couldn't stop thinking about doing it with you. I found a copy of Cosmopolitan at school and read an article on how to do anal sex. I took notes and bought a plug from Ann Summers - a little embarrassing, but I thought it was necessary. I also got some KY Jelly and an anal douche. It wasn't easy, but I practiced using them.
After last night, I felt compelled to try it the next morning. It hurt a little at first, but I managed to relax and let it happen. The trick seems to be using double the amount of lubricant you think necessary and pushing out when the cock is going in.
You seemed to enjoy it, and I found the orgasm unlike anything else I'd ever felt. It was intense, starting in my ass and spreading throughout my body. After a few pulses, my clit joined in with the normal sensations. It was so intense that I moved involuntarily.
I was worried about hurting you, so I made sure to be gentle. You seemed to enjoy it quickly, and the way you came...
She chuckled. "The funniest part was the orgasm. It was completely different from anything I'd ever felt before. Extremely intense, and it started in my ass before spreading out. It was only after the first few pulses that my clit joined in. It was so intense that I moved on my own."
"How were the sensations? Did they feel good?"
"Hard to say, they were very different and took some getting used to. I wasn't sure at first, but as I've mentioned before, the brain is the biggest erogenous zone, and you played a big part in getting me there. Your idea worked out well."
"Would you do it again? With me?"
"Yes, possibly. That all depends. With Colin, I'm not sure. Pushing something big up there without being considerate of my experience is intimidating."
As I digested everything she was saying, a beautiful smile spread across my face. I had taken your anal virginity and given you an extraordinary experience, including a unique orgasm. You reminded me that when I leave tomorrow morning, it would be the last time I can enjoy your body and the last chance I have to ravage my teacher. So, I asked:
"Could I now make love to you?"
I pondered for a moment. We'd had sex energetically, vaginally, and anally. Could I now make love to you? That remained to be seen.
Read also:
- Senior Year at Sommerville High Ch. 10
- Sylvan Courtyard 6: Career Assist
- No desire to debate
- Live without regrets Pt. 03
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