Background
It all began on a Wednesday night early last summer in Rosanne’s back yard. Finding ourselves alone following her “Welcome to Summer” party, Rosanne’s curiosity and my hormones set us on a journey of sexual exploration that led directly to this story.
That night, Rosanne’s parents were playing cards with members of their large extended family at her uncle’s house just down the street, something they did regularly on Wednesday nights. This continued all summer, but by fall the card-party had moved along with her uncle to Mamaroneck, a town about 40 minutes away. For Roseann and I, what started on a blanket in the shadows behind the garage, had since moved indoors to the comfort of Rosanne’s bedroom.
In the intervening months, we had discovered and explored many of the pleasures of sex. But, there was something that still eluded us – something that Rosanne really wanted. Tonight, Rosanne was gonna get her wish, and we’d both experience something unforgettable.
My Story
The backyard was dark and the kitchen door unlocked. After entering, I quietly closed and latched the door behind me. The living room was in the front of the house – a bathroom midway down the hallway. It wasn’t unusual for me to make a bathroom stop before joining Roseann. But tonight, she had left the bathroom light on for me. I entered and closed the door. Something awaited me – part of our plan. A milky-white ‘bullet’ she had left in a little dish on the back of the toilet. I was still a child the last time one was used on me – it wasn’t pleasant – and tonight I would do it myself.
It felt cold as it slipped in, its shape designed so the induced contractions of my anal sphincter would drive it up into my rectum. I could feel it moving deep inside me, and waited to see what would happen. But after a few moments, there were no unpleasant effects (those would come later). So, I pulled up my pants and washed my hands.
Rosanne was waiting for me in the living room. We each were dating others, but we had been getting together for sex-play on Wednesday nights since last June.
We kissed and I lightly caressed her arms.
“The usual?” she asked.
“Yeah.”
I took a seat on the couch as Roseann placed a cube in each glass before pouring our bourbon. Ever since we moved our Wednesday night sessions inside, sitting and having a drink together was how we chose to start our evenings together.
Tonight, she got right to the point, “Did you do it?”
“Uh-huh.”
“Then, no second thoughts?”
“No.”
She raised her glass, “Good. Here’s to one more try!”
She settled in alongside me, we clinked glasses and drank a toast to our latest attempt to fix my problem. The nice thing about being intimate friends was that we could talk about things – anything – even topics that might be difficult for lover’s fragile egos. Things like Rosanne’s ongoing failure to reach orgasm before I finished. She liked cunnilingus afterward and had strong orgasms for me, but she wanted to come while I was still inside her. I understood.
We had already tried lots of remedies – commercial sprays, creams, gels, and several manual delay techniques she found in the girly magazines – all unsuccessful. Tonight, was gonna be something new and very different.
The ‘little helper’ was a drug-delivery suppository made by the pharmacist in a small village in Italy. Rosanne’s cousin used them with her boyfriends and sent a small tin to Rosanne for her birthday. Cone-shaped and nearly 2-inches long, the small end was a rounded point and the large end was blunt and over half-an-inch in diameter. Rosanne had four, and had shown them to me last week. I was reluctant at first, but she explained how they worked and how we would use one. More important, it was clearly something she wanted to do, so we had talked it over and I agreed to give it a try.
Tonight, we sat together sipping our drinks, she put her hand on my thigh as we began kissing. She knew how much this turned me on. I knew, she liked me to lightly caress her breasts and kiss her neck. So, this was how we usually began to get each other in the mood for our trip to the bedroom. Tonight, we had to wait for my laxative to work – a necessary preliminary to ‘clean me out’, so the little helper would do its job. Even as we started petting, I was beginning to feel the effect of the Ducolax deep in my gut. I tried to ignore it as long as I could, but the feeling persisted and was getting stronger.
She noticed and teased me, “Are we feeling a little distracted tonight?”
“How’d you guess?”
“I tried one this afternoon – just to see how long it’d take. I only lasted a few minutes before I was having serious cramps.”
Now, I was feeling the urge to go and the cramps had started, but weren’t too bad, yet. I was hoping I could last a little while longer.
Finally, I had to warn her, “I can feel it working.”
“Hold it as long as you can. OK?”
“I know.”
We had talked about this last week. But, the urge to defecate kept growing stronger and the cramping got worse. Soon, I had to make a quick trip to the bathroom – getting to the toilet just in time for the relief of letting go. But, even when I was done, the cramps persisted. I felt light-headed, and was covered with sweat. I sat there on toilet for what seemed a long time before I began to feel a little better – embarrassed that I was taking so long. I waited a few more minutes, then even though I wasn’t really ready, I flushed, washed my hands and rejoined Rosanne.
“You look terrible ... are you OK?”
“The cramps were a lot worse than I expected. I just hope it did the job.”
She took me in her arms, “Let’s just sit for a few minutes.”
As she held me she continued, “This afternoon, I had to lay down for a while, before the cramps went away.”
I was happy for the chance to recover. I still felt sick to my stomach and the cramps still hurt. It felt good to lay my head on her shoulder. Rosanne was patient, I knew she would let me decide when I was ready to continue. We sipped our drinks. After five minutes or so the cramps were fading, and I was beginning to get interested in getting started again.
I lightly brushed my hand across her breast. She wasn’t wearing a bra, so I could feel her erect nipple through the soft cotton blouse. She lay her head back on the couch as I circled the nipple with my finger. My attention elicited a quick catch-breath and then a soft moan. She really liked when I did this and wasn’t afraid to let me know.
I stroked my finger-tips along her face, gently turning her toward me, so I could kiss her lips. After lightly kissing her soft lips, I felt her tongue feeling its way into my mouth. Rosanne was so good at this, I almost came in my pants the first time she did it. But, tonight it was no surprise and I enjoyed being aroused by her French kisses as our tongues intertwined in a lovely delicate dance.
I ran my hand down from her hips along the outside of her thighs. She instinctively parted her legs for me as I lightly ran my finger tips up along along the inner part of her thighs. I could feel her passion rising in the way her tongue probed my mouth. As I slowly let my hand settle onto her crotch, I felt her body begin to tremble in response to my touch. Her pants were already damp. There was no rush. I took my time, letting her excitement keep building, and soon her hand was feeling its way toward my penis.
She whispered, “I love the way you make me feel.”
I replied, “Time to get a little more comfortable?”
She didn’t reply, but simply got up and took my hand. Leaving our drinks unfinished, it was time to make our trip to her bedroom. This moment always sent a shiver of excitement down my spine – even more so tonight since I was anticipating something we’d never done before. We had talked about all the details last week and I thought about it all week. She was gonna put some drugs inside me to delay my orgasm. I couldn’t stop fantasizing about it all week – imagining her doing it each time I masturbated.
Her bedroom was only lit by a few night-lights plugged into the baseboard sockets. The ambiance was perfect, reminiscent of our first weeks last summer in the back yard. We kissed and began to undress one another. Once I unbuttoned her blouse, I tenderly kissed her nipples as she let the blouse fall to the floor behind her. As I kissed and sucked her nipples, she went to work on my pants. I kicked off my shoes. I already had an erection, which she wasted no time liberating – carefully lifting the elastic waist-band of my briefs over it. Once I stepped out of my pants, she had me sit on the bed, knelt between my legs, held my erection with one hand and gently pushed me onto my back with the other. I waited to feel her take me into her mouth.
She had learned how to take me deep without ever letting her teeth touch me. My body language let her know how good it felt. She knew exactly how far to take me, so I was hard as a rock and eager for more.
Once she was done, I removed my shirt and pulled her up onto the edge of the bed next to me. She knew the drill – laying back and lifting her butt, so I could remove her pants and panties. I pushed her legs apart, tasted her pussy and ran my middle finger up inside her wet pussy, while gently sucking her clit.
When I thought she had had enough, I sat down beside her, leaning over her as we resumed kissing and petting. We both knew what was next and were enjoying a few more moments of familiar things before moving on. I wasn’t quite sure how to make the next move, but she had no such qualms.
“Well sweetheart, are you ready?”
I stuttered, “You mean...”
“Yes, dear. It’s time for your medicine.”
Still a little anxious I simply said, “OK.”
“C’mon. Up on your knees.”
So, this was it. It seemed so quick. I was anxious, but I got in the center of the bed and positioned myself the way the Rosanne did when we did ‘doggy-style’.
I nervously asked, “This OK?”
“Yes, sweety. Stop worrying so much. My cousin says her boyfriends really like it – what it does for them. I’m sure you’re gonna, too. So, just relax.”
She reached over to the night table where she got a box of tissues, the tube of K-Y Jelly and the small tin containing the ‘little helpers’. We both hoped it would delay me long enough for Rosanne to have an orgasm while I was still inside her.
I turned toward her laying my face on the cool sheets, as she got everything ready – opening the tube of KY and the small tin.
As she got in position beside me, I said, “You know, I’ve been thinking about this moment all week.”
“I have, too. I’m pretty excited about putting it in you. How’s it feel to be the one who’s gonna get penetrated for a change?”
Maybe that was what I had found so titillating – something about her pushing it inside me – penetrating me. Something she’d never done before. And, not knowing how it would feel or how my body would respond.
She didn’t wait for my answer. I felt her finger applying the cool K-Y Jelly around my anus and then gently probing – trying to slip her finger inside me. My whole body tensed as I felt myself begin to open for her. She sensed my reaction and withdrew.
“C’mon now. Relax for me. ’K?”
“Yeah. Sorry.”
She squeezed out another dollop of K-Y onto her finger, applied it, probed again, and this time slipped in.
Once she was inside, I relaxed and breathed out, “Ummmm.”
“Oh! You like that? Think how good it feels for me when you put your little dickie inside me and how much I want to feel it in there when I come.”
I’d never really thought about it – all I knew was how good it felt for me to be inside her. I no sooner pondered this than I felt her finger slip out – and then something hard and cold pressing against me. She was doing it – slowly at first, but firmly and without hesitation. It felt bigger than I expected. By the time it was nearly all the way in, the large end was forcing my anal sphincter open. But, once the largest part past my back-door, the suppository was quickly drawn inside me just like the little one had been.
Not knowing what to expect, I felt a rush of adrenaline as the coolness was carried deeper. For a few seconds, I could feel it, big and cool. But soon that sensation passed. In its place was a warmth that seemed to radiate throughout my pelvis, just as Rosanne had described.
Her work done. She wiped her finger on a tissue and lay down on the bed beside me – head propped up on her elbow.
“Well, can you feel it?”
“Uh-huh.”
“How’s it feel … warm?”
“Uh-huh.”
“Good. It’s gonna take about five minutes. C’mon, lay down alongside me.”
I snuggled alongside her, and she pulled up the covers, glancing over at the clock on her bedside table. Maybe we had to wait, but that didn’t mean I couldn’t have a little fun in the meanwhile. So, I began caressing the erect nipples of her bare breasts. In time, my hand found its way down her abdomen to her wet slit. I ran my finger up and down the length and paused to lightly circle her clit. I was ready and anxious to get started.
I pleaded, “Rosanne, I want you. Now.”
“I know, sweetheart. I wanna feel you inside me, too – just a few more minutes.”
Then, she came closer and purred in my ear, “Today’s safe. You know what that means.”
“U.P.?”
“Uh-huh.”
U.P. meant ‘unprotected’ – no condom for me, no contraceptive foam for her, something we both truly loved. But, it promised an even quicker trip to nirvana for me to drop my load, which was exactly what I didn’t want. I could feel the ‘little helper’ working on me – at first a warm feeling radiating throughout my pelvis, then a tingling sensation just behind my penis – now just the warm feeling again.
Her hand had found its way to my erection, and she began lightly stroking me. I wanted her so badly, I could feel the skin stretched tight along the shaft of my penis. Finally, she glanced at the clock again,
“OK. It’s time.”
She didn’t need to say it twice. I was on my knees again, this time between her legs – my hands on the bed close-beside her shoulders – looking down expectantly into her eyes. We had decided on missionary last week, so she could watch me. Our lips met in hungry kisses as she reached between my legs where my almost-painfully-erect penis dangled ready to do its job. As usual, she took it delicately between her slender fingers, while spreading her labia with her other hand. Then lifting her hips, she guided me into her vagina. All I could think was ‘God. I hope this works’. I felt my glans touch her labia, then enter her as she coaxed me inside. Once my glans was inside her she put her arms around me and kissed me, as I continued to enter her very slowly. I savored the feeling of her warm vagina sliding up along the taut skin of my bare hyper-sensitive penis. I pushed deeper until my pelvis was touching hers, my balls lightly resting on her cool-wet ass. It felt so good! I always paused for us both to enjoy this magical moment.
After savoring her inner warmth, I withdrew slightly and let myself settle into her again – this time rocking my hips slightly from side to side. The tip went deeper, as her labia spread around me. I cradled her head on my hands and gazed into her eyes for a long moment.
“Oh Rosanne, it feels so good, doesn’t it?”
She whispered, “I wanna come. Please. Make me come.”
Then I began gently working myself in and out – just a little at first – then a little more – and soon, the nice long strokes that we both loved. Each time my testicles lightly slapped against her bare wet ass. At this point, the effect of watching her, smelling her, feeling her was overwhelming and would bring me to orgasm in a minute or two. But, tonight ‘little helper’ was working its magic on me and even though everything felt just as good as always, the urge to come didn’t develop. Instead, I found I could keep going … and going – deep, long gentle thrusts.
We were past the point where she should have expected me to come … I looked down at her +and smiled. She seemed to know it was gonna be her night. Her eyes were already half-closed and dreamy – her expression had a far away look. After a few more strokes, she closed her eyes. Her breathing became deeper and her expression more focused each time I penetrated her. Her breathing became labored and irregular – her mouth opened for little catch breaths as she began to quiver. I watch the delicious expression on her face evolve as the tension built.
I had watched Rosanne orgasm before – either masturbating her or doing cunnilingus. I had felt the spasms ripple though her body and heard her as she struggled and vocalized. But never, with my penis up inside her; never, holding her in my arms; never, feeling her press herself onto my erect penis with the same urgency that I felt when I was about to come.
Soon, her body began to tremble and shake as the neurological firestorm of her orgasm ignited. I kept thrusting, each time holding myself deep inside her, pinning her to the bed for a moment and feeling her struggle against the daemons that were having their way with her.
When the full force of her orgasm hit, I held myself inside her as she writhed and squirmed with delight. It was amazing to watch her so completely abandon herself. I was happy. I had finally been able to give her what she wanted so much.
In time, her climax was passing and I had completely forgotten myself – but then I experienced an all too familiar sensation. Watching her come had had its effect on me. My body was getting tense. Even though I couldn’t feel it, emission had already begun. Semen was flowing into the base of my penis, where my urethral bulb was being stretched to accommodate it. Only a few seconds more. Ejaculation had become inevitable - a feeling every male reader knows.
Her orgasm was nearly spent, but she felt my body tense and knew what was coming. She held me tight as I thrust one more time deep inside her. I rocked from side to side, trying to force myself deeper. The next moment, I was overtaken by my first ejaculation – delivering a large bolus of semen and triggering my own orgasm. That first squeeze always felt so good. I just wanted to pour every bit of myself into her. I grasped her shoulders and pulled her down onto me, grinding still deeper before the next ejaculation rocked me. To my surprise, my orgasm drove her to half a dozen little climaxes coincident with my gradually diminishing series of ejaculations. She reached her lips toward mine, and we kissed until the last spasms trickled though our bodies and dissipated. When it was all over, she softly exhaled,
“Oh, wow.”
I felt the same and could only respond, “Rosanne.”
I was totally spent – overcome by an overwhelming feeling of fatigue. Still breathing hard, we stayed coupled, my penis deep inside her and my head alongside hers, breathing her scent and cradling her in my arms. We were both covered with perspiration, just beginning to catch our breath and reflecting on what we had just experienced. I couldn’t think of what to say, so I gently sprinkled kisses on the side of her face.
I was about to tell her how good it felt, when we both started to giggle – and couldn’t stop for a long while.
We had a lot to talk about, but not now. It was time to simply enjoy the warm afterglow of sex. Tonight for the first time, we had touched the ‘holy grail’, coming together.