Each of us has our own stories. This one is mine.
I’d been dating the same girl since my early days in Junior High. Theresa was a sultry looking woman even then. As the years passed, through High School, on through graduation, we began to consider the possibilities of marriage. Unlike many of our peers, we’d actually both remained virgins during all this time. It was our intent to “save it” for the wedding night as Theresa had once told me during a particularly heated evening together when we had both gotten a little too close in “going all the way” as it was referred to back then.
Obviously we had graduated to various forms of intimacy prior to this point with Theresa over the course of time giving in to my promptings and urgings one small step at a time. Which was exciting in and of itself, as these were small little advances over a fairly long period.
Theresa had a beautiful olive complexion. Considered ‘short’ at just an inch under five feet, she had long dark beautiful hair that cascaded well past the round curvature of her ass. She also had large full breasts, having been full figured for about as long as I can remember, which had been one of the reasons admittedly I’d been attracted to her.
It was during our final year of high school just before graduation that Theresa’s mother and father divorced. I’d always respectfully called Theresa’s mother Mrs. Ortega prior to this time, but was frankly at a loss as to what to call her shortly after their divorce was final. As was most often the case I was over at Theresa’s on a Friday night as we were wont to do, anxious for Anita, Theresa’s mother to go to work so we could ‘watch’ TV, though we usually ended up fooling around on the couch, or in some rare instances, her bedroom. It was this particular night that my relationship became far less formal than it had been with her mother.
Since we were both already eighteen, each of us had a bit more leeway and freedom than even some of our other friends had, which included my being there even though we’d be left home alone together.
“Ricky, please call me Anita.” She’d said. Anita was the only person who ever called me that. Even Theresa called me Rick, unless she was mad at me for one reason or another, calling me far worse names. But Anita’s favorite show was ‘I Love Lucy’ and because of that, she always referred to me as “Ricky” though I was glad she didn’t include “Little” when she said it.
Theresa was the spitting image of her mother, though Anita didn’t have as long as hair as her daughter did, she still wore it just reaching the shoulders. It was obvious where Theresa got her incredible breasts from, as Anita’s were just as large and full, though I had never seen them of course. Taller than Theresa by a few inches perhaps, she easily could have passed for her older sister rather than her mother, which she always seemed to get a kick out of doing whenever they’d gone out shopping together.
Anita was in a particularly interesting mood that night as she finished preparing to head off to work. “Your brother should be home in about an hour.” She informed us. “Or possibly even sooner…” She added giving us a look that implied all sorts of things. “So I guess you two can’t get into too much mischief before then.” Heading off towards her bedroom to finish getting ready, Theresa and I looked at one another, surprise etched in her face as much as it must have appeared to be in mine.
“Do you think she suspects anything?” I asked.
“Well, a few month’s ago mom asked me if I was still a virgin, I told her we both were.”
“You’re kidding!” I exclaimed somewhat alarmed.
“Actually I think it put her mind at ease a little about leaving us alone together as often has she has, though she still prefers it if someone else is here of course, but I told her we were saving it for when and if we decided to get married.”
I sat there with mixed emotions. Nervous to some extent that Theresa and her mother had even had this conversation. But I was also a little surprised to find the fact she’d actually talked to her about it at all…finding that to be more than just a little stimulating.
One thing Theresa enjoyed doing was taking chances. Not really big ones mind you, but things that were a little risky and slightly dangerous. She’d no sooner finished telling me about the conversation she’d had with her mother when she suddenly pulled the sweater she was wearing up and over her breast, pulling up the cup of her bra in the process flashing her boob at me. With her mother in the next room, the likelihood of her appearing at any moment, it made the quick simple flash naughty as well as exciting. Theresa loved teasing me anyway, especially when she knew I couldn’t say or do anything about it. Seconds later her mother came out of the room preparing to leave for work. Theresa barely got her sweater back over her breast as Anita came walking back into the room. I wasn’t even sure she’d managed to pull the cup back over her boob, but at least her breast was covered when her mother had entered.
“Ok, well…I’m off to work, should be home around one or so,” she said. Anita worked as a waitress at one of the local bars. One of the things I admittedly found exciting, though keeping it to myself was the low-cut blouses she wore as apart of her “uniform”, along with a skirt though it wasn’t actually short, was slit up fairly high on one side revealing a goodly amount of thigh encased in black fishnet stockings.
Anita gave Theresa a hug and a kiss before leaving, and for a moment I thought she was actually going to give me one though she didn’t. She did wink at me however, and as Theresa had just shared the news with me that her mother knew “something” about our relationship, it made me more than just a little sensitive to that knowledge, especially when she included the wink just before leaving. Needless to say, I was very anxious to ask Theresa what else they had talked about the moment her mother had left.
Wanting to give Anita plenty of time in the event she forgot something, unexpectedly returning, I waited patiently for a few minutes before asking Theresa what else they’d discussed. Theresa had also taken that time to head into her bedroom where she removed the bra, though keeping her sweater on. I already knew beforehand that we’d be enjoying another session of “lick the titty’s” which I always looked forward to anyway, as did she. But knowing her brother would be home before too long, it was about all we could look forward to doing in the short amount of time that we actually had.
“Theresa? What else did you tell your mother?” I asked curiously. She laughed, finding it funny that I appeared to be as nervous about what they’d talked about as I was.
“Just things,” she said trying to beg off from telling me.
“What things?” I now pressed, more curious than ever. Which Theresa used as simply another tool to torture me with, as she simultaneously lifted her sweater giving me a good view of those marvelous full breasts of hers.
“Do you want to talk? Or play with these?” She asked, holding her sweater above her bare boobs.
As we both new her older brother Michael could be home anytime now, I opted for some breast fondling and nipple sucking instead.
Though Michael and I got along ok, he was particularly protective of his sister, watching us like a hawk whenever he was around. He had told me early on in our relationship when things started to finally ‘look’ serious, that if I ever “touched” his sister…meaning intercourse with her, he’d punch my lights out. I found that to be quite ironic, as he had had quite the reputation himself back in high school. But then double standards seemed to be more in vogue back then than they are today.
As I’ve already mentioned, Theresa had large boobs. About the only way to describe them accurately is to say they had a ‘tear-drop’ shape to them with incredibly large dark areola’s capping each one. I particularly loved the way they looked whenever I managed to convince her to lie down on her back, a position she personally hated. Her breasts were so large, they appeared to melt off of her chest like hot wax, and though she hated the way they looked when they did that, I for one loved it.
Theresa leaned back upon the firm cushions of the couch. She really must have been horny, her breasts spreading flatter against her chest as she did, knowing how much I enjoyed seeing that, though she still managed to cup them with her hands before they had completely flattened, which she did in offering them to me to come play with.
I put my questions for her aside and dove into the sea of tit flesh that awaited me. I still had several unanswered questions to ask, but at the moment, two hard pointed twin hills were beckoning to me.
As we’d both feared, twenty minutes later the sound of her brother’s souped-up Chevy pulling into the drive alerted us that our sexual escapades were pretty much over for the evening. Especially when it became obvious that his buddies were with him, something Theresa hated as much as I did as they were always hitting on her, regardless if I was around or not. Immediately we retreated to the backyard where we’d at least have some measure of privacy, especially after the sun went down. The best part for me of course, was it allowed me to once again bring the ‘subject’ of what she and her mother had discussed together.
“So…what exactly did you tell her about us?” I asked.
“Well, like I said, I told her we were both still virgins and that we were planning on staying that way.” She said it looking at me with an assuring stare that said she meant to keep it that way too.
“She asked if I’d let you feel me up.”
“She did? What did you tell her?”
“That you had.”
“You told her that?” I said incredulously. “Yeah,” she said drawing the word out, immediately alerting me to the fact there was still more.
“What else did you tell her?”
Theresa knew this was just the sort of teasing chat she enjoyed torturing me with. “She asked if we’d done anything more than that.”
“What did you say?”
“I told her the truth, that we’d touched one another intimately.”
“You actually used the word intimately?”
“What’d you expect me to say? That I’d jerked you off while you finger-fucked me? So yeah, I said intimately, but she knew what I was telling her.”
“Holy shit!” I whistled softly. “Did she freak out or anything?”
“No, all she said was that if I ever wanted to talk to her about it, or wasn’t sure of anything, all I had to do was come to her. Mom made it very clear to me that she didn’t want there to be anything uncomfortable between us in my asking, and that I was free to talk to her about it anytime.”
“Wow,” I said breathing only slightly easier. “I’m surprised she didn’t want to have a chat with me too!”
Theresa laughed, “Actually…she said that one day she just might do that. I think she was only kidding though, but you know mother, she could do it just to freak us both out.”
We played a little touchy-feely after that for a while until her brother discovered where we were, then he and his friends came out back annoying us both until I finally figured it was time to leave.
Theresa also worked as a waitress, though she worked at a cafe-coffee shop. She worked the afternoon to early evening shift however, which still left us most of the evenings over the weekend. We’d both been looking forward to this particular Saturday evening for quite a while now. My parents had a dinner party they were planning on attending which would leave us free to enjoy a nice quiet evening together at my place… undisturbed. Being an only child did have its advantages from time to time. The only minor concern we had, the place they were having dinner was only two doors down from where we lived. Still, it afforded us an opportunistic window that neither one of us was willing to pass up. Again, Theresa always got a little wilder if there was an element of danger or excitement involved. This particular situation certainly had enough of that with the possibility of their arriving home unexpectedly, catching us in the act.
I waited until they’d been gone for about a half an hour, then drove to her place and picked her up. Theresa lived less than two blocks away, so it was a quick five-minute drive there and back. We immediately headed into my bedroom, with the anticipation of this being a very special night for both of us. I had been hoarding candles, incense, even buying her a dozen roses just for the occasion. Within minutes of arriving, Theresa had gone into the bathroom, putting on a very sexy, very revealing nightgown she had purchased for this particular night as well. And although we would not be engaging in sexual intercourse, we had been discussing “oral” sex now for several weeks. Tonight was the night we’d decided to explore this particular little aspect together.
I was already in bed, naked, waiting for her when she came out of the bathroom. She was beautiful! The fact she was wearing the sexiest outfit I’d ever seen her wear before probably had a lot to do with it. But regardless of that, when she walked into my bedroom with that white “teddy” nightgown on, my cock immediately sprang to life with anticipation of things to come.
“Oh baby, you look beautiful!” I told her meaning it. And she did. The fabric was shear, just allowing a peek at the softness and curve of her flesh hiding beneath it, the darkness of her chocolate colored nipples really standing out in stark contrast to the white sheer fabric barely concealing them as she stood before me.
“I sorta had an idea you’d really like this one,” she stated, and then came over lifting the covers and jumping into bed next to me.
Though we had on some few occasions played with one another, they had all been mostly under the cover of darkness, either in her back yard, at the drive-in, or just sitting in my car in front of her house. Neither one of us had actually up until this very moment, gotten a clear and unobstructed view of one another in real light before now. As Theresa lifted the cover, she saw the firmness of my erection, and I watched as her eyes actually widened before placing her hand, wrapping it around me, stroking it all the while laying there actually looking at me.
I immediately began touching her breasts as they were so conveniently available the way we were laying, even though I did so through the thin fine material of her nightgown.
“Nice,” I moaned pleasurably, feeling her hard little nipples stiffening at my touch. “That feels good,” I added as her soft hands continued to fondle and playfully stroke my cock without serious intention.
“Yes it does,” she replied as I gingerly continued to trace the outline of her full breasts and nipples through the thin fabric, though at the moment I was in want and need of touching her elsewhere too.
We were both probably more excited than either of us had been before too, we’d already agreed that this night would be special enough, having decided to take things to the next level, as we’d indicated to one another with the dozen roses I’d given her, and the damn sexy nightgown she’d put on for me.
“Yeah?” I moaned almost dream-like.
“Just remember, we’ve promised each other not to take it any further than this,” she stated, though the “this” hadn’t quite happened yet.
“I know,” I said simply, only half meaning it.
“I mean it,” she said again, “promise me.”
At the moment, with my hard stiff cock in her hand, I would have promised her anything. “O.K., promise!”
A moment after that, I pushed her down onto her back and began untying the dainty little bows that held her top together. Soon I had more fully exposed her breasts, and secretly sat there enjoying the way they looked as she lay on her back, running my finger over and round her nipples, then down and beneath the hard firm curvature of each.
“Are all men like you?” she asked somewhat teasingly.
“What do you mean?”
“Tits, what is it about tits that arouses you so much anyway?”
“Do you really have to ask that?” I questioned. “Hell, I don’t know…they just do! Especially yours!” She sat up in bed then forcing me back to some extent.
“What do you mean? Especially mine! Who else’s boobs have you been looking at anyway?”
“No ones!” I said defensively, though I figured those in a few of the men’s magazines my father had didn’t count.
“Oh, so you haven’t looked at any other woman’s breasts and wondered what they looked like huh?”
“I didn’t say that,” I said honestly, then wondering if I should have admitted that after saying it.
“Oh? Whose?” She pressed.
“Well, your mothers for one.”
“Well MY mother’s too!” I added to that, making things even worse.
“Boobs are boobs,” I said defensively, adding to the hole I was digging myself into.
“I’ll remember that,” she said reaching down, closing her gown.
She laughed, allowing her gown to open again.
“So…you’ve wondered what my mother’s boobs look like huh? Not to mention your own mothers.”
I didn’t tell her I’d actually seen my own mother’s breasts on several occasions, mostly by accident especially as I’d gotten older.
“Listen, its just a natural curiosity is all,” I tried explaining to her. “Anita’s got breasts nearly the same size as yours, so it’s like wondering what yours will look like when you’re her age is all.”
“Bet you would like to see them if you could wouldn’t you?”
I didn’t answer that, I wasn’t about to and leaned forward kissing her instead. That at least got us off the subject, especially when I slowly began making my way down to her breasts, kissing them, and sucking them for a considerable amount of time until her breathing told me she was becoming very, very aroused.
I made my way slowly downwards from there, kissing her tummy, gently flicking my tongue around in her naval. Theresa responded to that, realizing as I did that what I would soon be doing to her elsewhere.
But to be honest, I was sailing into uncharted waters here myself. All the information I’d been given had come from an older brother of a friend of mine. He had given me a few basic pointers is about all, telling me that doing this to a woman was a sure-fire way to get her to fuck. That really wasn’t my primary objective here, but it had made me curious that if it was that good, or felt that good…then hell maybe. And so much for the promise I’d made. But that still remained to be seen at the moment.
Theresa was also wearing a matching pair of panties too of course, nearly as sheer as the top so I could see the tiny little patch of fine dark pubic hair that lay beneath the surface as I moved down towards her there. Nervous as I was, and as she was, I simply kissed her there, trying to work out the details as I did that, but she moaned softly nevertheless, so I continued doing just that for a bit longer. They were in fact, simple kisses, kissing her pussy through her panties, but it seemed to be having some sort of an effect on her, so I continued, though I now began to actually lick her through the material with my tongue. In doing that, I made her crotch wet from the outside, but she was likewise making it wet from the inside, and I could literally taste her and smell her while doing so. I began to press my tongue into her more forcefully until she solved the dilemma I’d been struggling with for me. The next thing I knew, she had drawn her feet up towards herself, lifted her ass, and in one fluid motion had yanked down her own panties flinging them half-way across the room. Settling back once again, I now looked down directly at her, truly and honestly seeing her exposed pussy in all its splendid glory for really the very first time.
Even then, I wasn’t sure where or how to begin, so I did the first thing I was a bit more comfortable with, and slipped one finger inside of her, though I’d actually never witnessed myself doing this before. She once again moaned, letting me know as she did so that she liked it, that it felt good, which is when I then snuggled back down between her legs and got serious about really licking her this time, which I proceeded to do.
Each of us has our own stories. This one is mine.