Chapter 8

We kept our distance until we went inside the back door of the convent. When the door closed behind us Mary Cecile eagerly took my hand and led me back to her room. She closed the door then turned and raised her face to mine and said, “I have never kissed a man before.” My immediate thought was, A Man? I’m not even fifteen yet. “Have you kissed any girls?”

I admitted to her that I had kissed Sister Natalie several times and I had kissed Kathy Warren, my neighbor. With Cassie (Sister Natalie) it was a learning experience, with Kathy both a learning and teaching experience. Each time the outcome was successful, it was titillating for both of us. Leaning down I kissed Cecile’s lips. They were tense and hard. “Relax Cecile,” I said, “make your lips soft.” Her cheeks reddened slightly as her eyes sparkled with anticipation and her lips curled into a sweet smile. Tightening her lips into a tight pout she wiggled and tried relaxing, biting, and licking them before presenting them back up to me. I pressed mine on hers again and held the kiss for a bit while expecting that she would relax further. But they hadn’t softened much from the first kiss. I knew a sure way to make a woman’s lips soft, by having her give me a blow job. Even to this day I’m still amazed by that. At the time though, I couldn’t even bring myself to suggest such a thing to her. Taking hold of both of her hands I said, “Take a few deep breaths Cecile...”

She interrupted me by saying “My family always calls me Cissy.” I was touched by her urgent attempt to humanize our interchange.

“Take a few deep breaths Cissy.” She smiled timidly. “Then bite your lower lip like this.” I used my teeth like gentle meat tenderizers. She mirrored my actions. “Now, like you are putting on lipstick, do the same to your upper lip. This time when our lips met hers felt softer. It was a much nicer kiss which I broke and said, “That’s much better Cissy.” She blushed, put her arms around me and laid her head on my shoulders and kind of purred.

In a voice so quiet that I almost didn’t hear she murmured, “I’m a virgin Toby.”

With a loud chuckle I said, “Aren’t most nuns?”

Responding with a girlish giggle of her own she said, “Not even. Quite a few have lost their virginity before they become novices. And here at St. Bart’s it’s only two out of five. Everybody assumes that we all are, but few people take into consideration the molestation of young girls, many of whom escape their circumstances by joining an order. Then, many are molested by priests ... or are serviced by them depending upon who’s doing the talking.”

The information hit me hard. It was difficult for me to conceive that many girls had been raped or molested as children by members of their own family. I wondered if what Ray Warren and I were doing with his sister Kathy was considered rape or molestation. I’d heard some of the rumors about Father McNamara but didn’t really believe them. Later in life I’ve heard studies that say from one in three to one in four girls have been molested. In my trek through life, I learned that my high school girlfriend was molested by her uncle. My own sister was molested by our grandfather. So, while I thought about the numbers of nuns who might have entered their orders as non-virgins, I wondered what Sister Natalie’s circumstances might have been. Being a horny young teenager with raging hormones I didn’t want to do anything more than to get into another female’s pants. At the same time, I didn’t want to be responsible for pushing Sister Mary Cecile into something that she would be sorry for. “Are you sure you want me to do this with you Cissy?”

She instantly clutched me and told me that she didn’t want me to get away from her. “I’ve been dreaming about this for weeks Toby. I don’t want to be a virgin when you leave today. What do you think we should do? And how do you think we should do it?”

Though I’d been feeling inadequate for being so much younger than Cissy it was easy, even for a fifteen-year-old, to see that she wasn’t acting like a nineteen-year-old girl who was a nun. She could have been acting like what I had heard about what some sorority girls did at a frat party. She was the right age for that, but I was still a kid. True, I was gaining in confidence but at the moment with this new girl I didn’t quite know how to go about it. Not answering her question, I pressed my lips softly on hers again and caressed her back.

As she hugged me more tightly her elevated breathing became ragged. Her lips, having become much softer than our first two kisses, parted as if by instinct and she sucked my tongue into her mouth. Struggling to breathe she broke the kiss, gave me a full body hug and gasped, “Oh my goodness Toby, what’s HAPPENING to me?”

For me, having sex with a new female was a matter of urgency; I was pubescent, awash in hormones, arrogant because of my recent sexual experiences. Based on the four females I had fucked so far it seemed like all I needed to do with Cissy was to put my hand under her habit and pull her panties off if she was wearing them ... and someway get right into the action. But her bulky habit made it too awkward. “Are you really comfortable in this thing Cissy?”

Her eyes seemed to be begging me to get her out of the unwieldy tent she was in. For a youth my age I was extremely lucky, my first two experiences were done in complete nakedness. At that moment though, not knowing how to proceed with this “older woman” I laughed and made a joke, “I never really understood why the Church makes you dress like penguins Cissy. Right now, it seems a sure way to keep us from enjoying ourselves.”

There was no question about Cissy being ready and willing. And since we would have the whole day together, I felt sure she would like to be as comfortable as possible. Though I was relatively certain she had gotten naked with Sister Natalie in their get togethers I thought she would probably be shy being nude in the presence of a male. She wasn’t acting like she was looking at me in a cautious state of confusion though. I remembered how Sister Natalie had taken the lead with me. With Kathy Warren being younger it was more of an obedient, mutual decision. Besides, her brother Ray, who I figured had done it before with her, was there. I suddenly found myself in unfamiliar territory and realized that I would have to take a different approach with Cissy. Though our age difference was still an issue for me I realized that if I didn’t take command, it might have just turned into a fumbling party that could go off the rails. So, I manned up and gently guided her shoulder as I said, “Turn around Cissy and I’ll help get you out of this thing.”

Saying “Open Sesame” couldn’t have been more successful. Without a word she turned her back to me. As I unbuttoned her top button and zipped the back of her habit open, she undid her veil and removed her wimple. Peeling her dress over her shoulders I let the heavy fabric drop to the floor in a large black pool that surrounded her ankles. To my stunned awe it was like removing the drape from an alabaster statue at its unveiling. With her back still toward me she presented an interesting picture. Her dark brown hair was artlessly cut above her shoulders, her white skin glaring like the palest porcelain. Both her panties and her bra were plain white cotton. On her feet were short heeled black orthopedic, lace-up shoes worn over black cotton, mid-calf socks which were held in place with elastic garters. Standing 5’5” in her shoes her legs were attractively sculpted: her body was lithe, her back muscular, her skin unblemished and her figure girlish and shapely.

No Don Juan I cautiously said, “You’re a beautiful girl Cissy.” It seemed the right thing to say. I kissed the back of her neck and she shivered. Knifing my hands between her arms I slid my fingers inside the fabric of her bra, cupping the softness of her breasts.

Her shiver morphed to a tremor which was minor ... but still her first orgasm. Her proportions were larger than Kathy’s but smaller than Cassie’s. Emitting a kittenish sigh, she shrugged her shoulders as if she was trying to become smaller under the scrutiny of a stranger’s eyes. It was easy to unhook her bra strap from behind. When I flipped her shoulder straps over her shoulders, she crossed her arms to prevent the lingerie from dropping to the ground. “You don’t have to be embarrassed in front of me Cissy,” I said before reaching around and gently coaxing her hands away. As I eased her arms down to her sides, she offered no resistance. The white bra fell onto the pile of black fabric.

Pecking her neck, her shoulders, and her ears the way Cassie had shown me I cupped Cissy’s breasts and fondled them tenderly. As her chest heaved her neck and shoulders squirmed in kind of passionate embarrassment. Under the circumstances I was surprised to feel how her rather large nipples had hardened into nubbins. Not able to see them I sensed their largeness that made me think they were larger than they were—like milk duds. When I took my hands from her breasts and said, “I’m going to take off my shirt Cissy,” she bashfully crossed her arms in front of her bare bosoms again. Trying to forestall further awkwardness while out of the sight of her eyes I wanted to let her know exactly what I was doing. After dropping my shirt to my feet, I leaned my bare chest against her naked back. To my delight she pushed back against me. It was the most amazing feeling. If skin could sigh, her flesh seemed to be doing it.

When I removed her hands from her breasts, she not only allowed my intrusion she put her hands over mine and pressed them harder against her breasts before crossing her arms over mine in an arresting embrace. Realizing that she found the harder pressure more exciting I added weight to it. Then as Cassie had taught me, I circled her breasts in opposite directions. As her hips squirmed back and forth, she let out a pleased sigh, saying in a tiny voice that I could barely hear, “My goodness Toby this is such a HEAVENLY feeling.”

Keeping one arm around her body I cupped her breast while I unbuckled my belt with my free hand. Working the button on my pants open I wiggled my hips to free them from my waist and they dropped in a puddle of chino cotton around my feet. Putting my free hand on her unattended breast I moved them both in a circular massage. At the same time, I worked my feet out of my pants by stepping on one cuff with my other foot and then the other.

Both bare from the waist up, I turned her to face me and looked into her anxious, hesitant eyes. When I wrapped my arms around her and flattened her breasts against my chest she moaned at the new sensation and, with a quavering whisper, said, “Oh Toby, this is so WICKED.”

Smiling at her dismay I smirked which made her lips curl into a tentative smile that broadened to an impish grin. Her eyes seemed to twinkle like stars on a cold winter night as she said, “And it’s more exciting than I could have ever IMAGINED. With open hands I pressed her soft body to me then embraced her. She mirrored my actions with hers and as our lips came together for the fourth time, she parted hers. How natural this is I thought as the tips of our tongues touched and the slick bottom of mine slid over the velvety taste buds of hers.

Cissy was the second nun I had kissed, the third female. While still considering myself an inexperienced youth I began to realize that I was light years ahead of my peers. My experience was more than enough to feel confident in the expertise I had gained so far. As the soft touching of lips and exploring tongues sent shock waves through my body, I understood that each experience was adding to my skill. What was being confirmed for me was new to Cissy. She trembled like a bridge beneath the wheels of heavy traffic.

Both hungry for each other’s kisses we feasted on the other’s lips. Our breaths, going into her nostrils and out of mine, became as one. Our kissing increased the flow of our saliva that leaked down our chins. She followed my lead, but we were both boiling with excitement. Our kisses were new but sloppy and delicious. With our hands crossed on the small of each other’s backs we leaned back, scanning the face of our new lover, flushed and glowing, our eyes drawn to the magnetic gaze of the other. When I whispered, “You’re beautiful Cissy,” her awkward expression of disbelief morphed to the sparkling-eyed visage of a little girl in the throes of adoring love. I chanced a comment on something more personal, scanning her perky, large-nipple B cup breasts and murmured, “Your breasts are so pretty Cissy.” It was well beyond flattery. Hers were indeed the prettiest I had yet seen; Cassie’s were somewhat saggy, and Kathy’s were nonexistent.

Gazing up into my eyes hers became moist as she said, “Thank you Toby, I’ve always wondered what a man would think of them.” Once again, I was flattered at being called a man yet knew how silly the “Toby world” would think of me being referred to in this way. But I didn’t care; I just felt a surge of affection for this attractive and lighthearted Bride of Christ.

“Um Toby?” she said in a voice of almost stunned awe, “I feel your hard ... um ... p-penis against me. It feels so BIG.”

Though young I was a male whose manhood was being praised—the holy grail of egomania, I was a peacock needing to spread its fan. “Would you, like to see it?” I asked with eager hope.

Her eyes widened as she said, “YES, I’ve never seen an erect penis before.”

It seemed that the five-year gap in our ages was narrowing by the moment. Though young I had done things she never had. My privates had been shown, handled and had been inside a middle-aged woman and a teenaged girl—more than any of my friends I supposed. Just months away from embarrassment and uncertainty shared sexual activity was becoming comfortable for me. As suavely as I thought I could be I peeled my BVDs over my hips and wiggled them to the floor. Taking Cissy’s hands, I pushed us apart so she could get a full glimpse of what was pranging from my middle. Her response was even better than I could have hoped for: “My GRACIOUS Toby, how can all of that ... that THING even fit inside a woman?”

Trying to be as cool and original as possible I said, “Gently.” I couldn’t believe I said it but boasted, “I’ve been inside a grown woman and a girl just a little younger than myself.” In a way I hoped that she hadn’t really heard me say that.

Tears welled in her eyes as she said, “But the hole in my v-vagina is so tiny. It must hurt terribly. I’m frightened Toby.”

As I gently embraced her—we were just the right height for one another—and my up-slanted cock slid between her legs, its head skating along the puffy lips of her pussy. Cupping the cheeks of her bottom I murmured, “I can feel the wetness leaking between your lips Cissy, that means your vagina is getting ready for me, you’ll be well lubricated.” I said it with the authority of knowing both Cassie’s and Kathy’s vaginas that I had already slipped easily inside of.

But her alarm hadn’t been assuaged. “I just don’t KNOW Toby.”

Hating the words that came out of my mouth I replied, “We don’t have to do it Cissy if you think it is too much for you,” but as much as I wanted to fuck her, I wanted to be considered a caring person by this sweet young woman. These kinds of feelings would deny me a good degree of sex by the time I was finished sowing my wild oats. But in my later years I learned how well they served me.

I want to Toby, I want it so BADLY, if only just this once. But I’m afraid that I’m too small for your-your THING.”

New at it but learning the art of selling myself I said, “But Cissy, if you would have been here with Father McNamara what do you think you would have done?”

With her arms wrapped around my neck she tightened them, almost choking me. “I don’t know. Maybe he isn’t as large as you. I-I suppose I would have done what the other sisters had done and let him have his way with me.”

“Cissy,” I said, prying her arms from around my neck, “Has Sister Natalie told you about me?” Based on the conversations she and I had last week and this morning I thought she had. But she hadn’t told me so.

“She has Toby.” There seemed to be no embarrassment or discomfort in her answer. “She told me that you would be very gentle with me. But I’m still frightened.”

“I fit very easily inside Cassie’s cunny.” (I knew Cissy would have called Sister Natalie “Cassie” when they did oral sex together. And I was sure that Cassie would have referred to her pussy as her “cunny.”

Staring deeply into my eyes she gaped at me and said, “Maybe Cassie’s cunny is larger than mine.”

“Look Cissy,” I said trying to ease her fears, “I did this with a neighbor girl recently ... she’s younger than I am. It was her first time. Once I broke her hymen (I lied about that) it went easily inside her.” I didn’t mention how carefully I had to do it.

“My goodness Toby Wakefield, you’re not even fifteen yet and you’ve done it with two women ... and you’re here with me.” With a sarcastic chuckle she said, “If you were a girl Toby, you would be called a slut.” Snorting she said, “What a guy.” As a woman she typically had little patience for a male braggart.

I knew that I should have bitten my tongue but couldn’t stop from saying, “You’re a nun Cissy and, as you say I’M here with you. What does that say about YOU?”

She glared at me then, with a mix of anger, remorse, and mirth she replied, “Oh Well, we’re BOTH bad.” She looked funny standing naked in black cotton socks and orthopedic shoes, with her hands on her hips. “Now, how do you think we should go about doing this smarty pants?”

Chuckling I said, “You’re really serious about this Cissy, aren’t you?”

With frustration painted on her face she shook her head and smiled the smile of the damned but determined. Opening her arms she said, “You’re in a convent, in a nun’s cell with her Toby. She’s standing almost naked in these STUPID shoes. Let’s stop fooling around and for the love of Christ get on with it.”

Sit down Cissy,” I said. Getting down on one knee I untied both of her “stupid shoes” and took them off thinking, God she’s such a beautiful girl and these shoes look so clunky on her. I rolled off her knee-length black socks then scanned her whole body. After having seen Cassie’s unruly, dark brown bush I was overwhelmed that Cissy’s was a neatly trimmed soft auburn triangle.

She patiently watched me appraising her body. As I centered back on her flat tummy and inviting bush she said, “And?” wondering why I was looking at her that way.

“Cassie’s pubic hair is bushy and unruly. Yours, Cissy, is um ... It’s beautiful.” The blush on her pale face looked like that of a demure porcelain figurine. “You,” I emphasized, “are such a pretty woman Cissy. I can’t even believe you would want to be with a boy like me.”