Part One
Timothy Barton had been a school chum of mine since we were both in the third grade. That was about 12 years ago. It was now 1974. Timothy and I, Patrick Angelli, were now 20 years old and inseparable friends and college pals. We enjoyed hanging out because we had similar interests and broad senses of humor. Timothy’s preferred avenue for humor was to make fun of himself.
Self-deprecation was something of a personal shield for Timothy. He preferred to mock himself before others did it to him. He had good reason for it. With a markedly crooked nose, rust-colored hair, large lips, and a big chin, Timothy was far from a good-looking youth. One comment he liked to make was “Helen of Troy had a face that launched a thousand ships. Mine was used as a loading platform.” Sometimes Timothy varied the second part of the joke to say he had a face that “stopped a thousand punches” or perhaps a “thousand pucks”. Any of those types of punchlines worked. Hey, if you can laugh at yourself, the world is your oyster. At least I’ve heard that’s the case.
Myself, I was not blessed with movie-star looks, either, but I was at least moderately handsome by reasonable standards. I often felt sorry for Timothy because so often people are judged—rightly or wrongly—by their appearance. Sadly, Timothy had a little sister named Gwen who was also lacking in beauty. She had an above-average figure for her age, but she too had a slightly crooked nose and smile, along with a prominent chin much too large for a female face. Being a homely girl is far worse socially than being an ugly male.
Two years younger than I was, Gwen was always friendly and vivacious whenever I visited the Bartons’ home. She was a cheerful and reasonably smart girl—and always had been despite Nature dealing her a rotten hand in the looks department. I was told that Gwen regularly brought home report cards with mostly Bs and a sprinkle of As. I could attest that she was an excellent cook and baker. These attributes got Gwen nowhere socially, though. Sadly, she had few friends at school. Teenage girls are a cliquish lot. It’s tough for awkward females like Gwen to break down barriers. Timothy, being a good brother to her, sympathized with Gwen’s plight.
One day Friday in April, I was talking to Timothy during our lunch break at college. I quickly noticed that he was not his typical jovial self on this day. When I asked him if something was bothering him, he admitted there was. He bluntly told me, “I’m worried that my sister will grow up lonely and unloved.”
That was quite a severe statement to make—and I told him so!
Timothy explained why he said that. “You’re not an 18-year-old girl, Patrick—and you don’t understand the problems that Gwen faces every day at her high school.”
“I suppose that’s true,” I agreed. “Since I’m neither your sister’s age nor her gender, how can I possibly know about such things? Then I asked him, “What’s the big problem?” That question was merely a politeness. I obviously knew what it was.
“Patrick,” Tim began, “you’ve been to my house several dozen times over the years. You know Gwen as well as anyone outside of our home. She’s fun, clever, and a good conversationalist. She enjoys a good joke, and can tell a few of them, too. She’s always friendly and really excellent in the kitchen! You’ve tasted the goodies that Gwen likes to bake. They’re terrific. In an ideal world, she should make an excellent wife someday in the future.
“Of course, the obvious trouble is no boys at her school are interested in her because...well, I’ll be frank about it: She’s homely. That’s an unfortunate trait we share as siblings. I can laugh at myself, but girls don’t have the same luxury. Being attractive is such a huge thing to them from early childhood. Nobody really cares that I look like George Foreman uses me as a punching bag. It really bugs me, though, that my sister is shunned because of her looks despite all the positive qualities she possesses. It’s brutally unfair!”
“Wow!” I exclaimed. “You really do care about your sister’s well-being, Timothy. That’s marvelous. I’m not sure I have anywhere near the same feeling about my sister, Emma.”
“Patrick, your sister is 22 years old, quite fetching, has her own apartment, and is engaged to be married, right?” Timothy pointed out to me. “Our situations as brothers aren’t very comparable. Because of me being the older sibling, there’s an expectation that I should look out for her. Last night I’d never seen Gwen so depressed.”
“What was different about last night?” I asked him.
“There is a big spring dance at Gwen’s school tonight, ” Timothy stated. “You must remember it from our days there. Anyway, as usual, no boy at her school asked Gwen to go to the dance. She tried to bait a few of her male classmates with gifts of her home-baked brownies, tarts and cookies. A lot of the boys rudely refused to accept them. Imagine that! By yesterday at lunchtime, when it was obvious she wouldn’t be asked to the dance, Gwen came home from school sick. She wasn’t physically ill; she was heartsick. Her plight broke my heart.”
“Gee, that’s awful!” I agreed. I quickly got the impression that Timothy was waiting for me to help out his lonely sister in some way.
“I’m starting to get the picture here, Timothy,” I said. “You have to realize that even if I wanted to take Gwen to the dance, I’m not allowed to do so because it’s restricted to students who attend her school—and for good reason. If that wasn’t the case, there would be an army of horny college boys our age crashing the dance to try to scoop up the good-looking, naïve, high school girls.”
“Hey, that is a great idea!” Timothy joked. “It’s too bad the organizers of the dance read our minds and stopped this sinister plot before it even started.”
I just laughed at Timothy’s irrepressible sense of humor. It was so much like mine.
After another lengthy pause, Timothy tried another approach. “As a favor to me, Patrick, can you come to my house tonight and spend some time with Gwen? My parents will be away visiting my mother’s sister’s family for the whole weekend, so Gwen and I have the house to ourselves starting at 5 p.m. I’ll let you in on a secret, Patrick: Gwen likes you a lot. She always has. She’d be thrilled if you came to the house to visit her instead of me. Just spend an hour or two with her. I think that would help cheer her up about missing the dance. Would you do that for me as a buddy?”
With only a bit of hesitation, I agreed to be Gwen’s in-house date for that evening. Apparently, Timothy’s tale of woe had served its purpose. Now I was feeling sorry for Gwen Barton, too.
“Great!” Timothy replied. “I’ll call Gwen on a payphone. She’s at home; she didn’t go to school today because she was still upset. Your presence tonight ought to cheer her up. Why don’t you come by at about 7 p.m.? Bring an overnight bag and stay until morning, if you want. As a goodwill gesture, I’ll even give you my bed and I’ll sleep on a couch.”
“That’s big of you, Timothy,” I stated.
“Not really, Patrick,” he replied. “I’m a bed-wetter and the sheets haven’t been changed for a week.”
I laughed loudly at that amusing comment and even applauded it.
Timothy couldn’t resist one more joke. “Let’s make a deal, Patrick: Let’s assume this sort-of date I’ve coerced you into accepting works out well for you. I ought to get something in return. If your good-looking sister Emma ever breaks up with her fiancé, kindly set me up on a date with her. She might secretly have a thing for an ugly 20-year-old friend of yours.”
Part Two
It was a cool April night, so I donned a light jacket for the six-block hike to the Bartons’ house on Ellis Street West. I was carrying an overnight bag. I figured after I’d spent a couple of tedious hours with Gwen to satisfy the promise I made to Timothy, he and I could spend all night watching the late shows on TV. I had looked through the TV listings earlier that day. I saw that one station had a Marx Brothers movie marathon that lasted into the wee hours of the morning. Both Timothy and I enjoyed Groucho’s comedic banter. Thus, I figured that would be the high point of my visit to the Barton residence that night. That proved to be incorrect.
It was five minutes to seven when I knocked on the door of 52 Ellis Street West. Timothy opened it. “You’re a bit early!” he said as he glanced at his wristwatch. “That must mean you are eager! I know Gwen is.”
I gave Timothy a bit of a dirty look before I insincerely said, “I guess I am, too.”
Timothy had just said he was pleased I had planned to stay overnight when Gwen emerged from her bedroom and strode down the hallway toward me. She was well overdressed for staying at home on a Friday night, especially since I was still clad in the same casual clothes I had worn to school that morning.
“Whoa! That’s a great dress, Gwen!” I exclaimed. I wasn’t exaggerating. It was a pretty shade of light pink. It was lacy and highlighted Gwen’s breasts—whose size rivalled those of the typical 20-year-old girls I saw every day at my college campus. All I could ruefully think of was, “Why can’t this girl be even average looking?”
Because she couldn’t read my mind, Gwen responded to my compliment. “I bought this dress long ago in anticipation of going to tonight’s dance. That didn’t happen, of course, so I figured I might as well put it on for you, Patrick. I’m glad you like it.”
“It’s very becoming,” I stated, and Gwen flashed me one of her crooked smiles.
Timothy interjected, “I hope you didn’t have too much dessert at home tonight, my friend. When she found out you’d be coming here tonight, Gwen spent most of the day in the kitchen. Look at this! She’s prepared the equivalent of a small bakery of homemade treats for you to enjoy.” He pointed to several overflowing plates and trays of cookies, squares, and other delightful snacks that had been set on the kitchen table and counter.
“Good heavens! You have enough snacks to feed at least half a dozen guests, Gwen,” I told her. That was likely an understatement. “You didn’t need to go to that much trouble for me. I’m not that special.”
“Well, I think you are very special, Patrick,” she replied. “That’s all that matters, right?”
Timothy stated, “You can’t argue that logic, Patrick. I’ll leave you two alone and head downstairs to the rec room. I’ve got some homework to finish for geography class and a couple of sporting events to choose from on the TV—if you consider roller derby to be a sport. I’ll keep the volume down.” Patrick ended his comments and descended out of sight.
Gwen handed me a plate and told me to load up on her baking. She took a few things to nibble on, too. “Patrick, let’s head into the living room and enjoy a chat,” she instructed me. “I don’t think we’ve really talked before.”
“Now that’s simply not true,” I insisted. “We’ve talked often, Gwen.”
“Not when we’ve been alone on something like a date,” Gwen pointed out. “I’ve never been to your home; I don’t even know the street where you live. Have we ever been alone together in the same room of this house, Patrick? I don’t think so.”
“I guess you’re correct, Gwen, if you put it like that,” I conceded as I looked at my plate. “I’m going to start with one of these squares with the red filling. It looks yummy. Is it raspberry?”
“Good guess, Patrick. Yes, it’s raspberry. They are my father’s personal favorites. Let me know what you think. I value your opinion.” Of course, it was delicious, and I happily told Gwen it was.
Gwen used my kind words as an excuse to sit beside me, embrace me, and kiss my cheek.
“Well, that was an over-the-top thank-you, Gwen!”
Gwen giggled slightly and said, “I’ve always wanted to do that, Patrick. The first time you came to visit Timothy, you were so nice and polite to me, I told my parents—ant Timothy, too—that I wanted you to be my boyfriend. I was six years old at the time.”
“So, you were interested in boys at the young age of six, were you?” I said with a smile. “I don’t think I cared much about girls until I was 10 or 11. That was when a classmate named Amanda Fletcher suddenly caught my eye. She was a real cutie whom I admired from afar. I recall her family moved out of town when the school year ended. Gee, that’s a name from the past. I haven’t thought about Amanda for years.”
“Luckily for me, your family stayed put, Patrick!” she merrily replied. Then Gwen gave me another warm hug and kissed my other cheek. She wasn’t interested in ceasing the hug. I gave in and hugged her, too. This prompted more kisses from Gwen with increased intensity. Of course I kissed her in return.
When the buss ended, Gwen told me, “Patrick, you are the first boy who’s ever kissed me after I’ve kissed him.”
That was a rather sad confession. “Want to do it again?” I asked her.
Gwen didn’t reply in words. She just embraced me twice as tightly as before and gave me a Hollywood-style kiss that I actually enjoyed. I discovered that despite her unfortunate homeliness, the well-developed Gwen was a fun girl to hug.
Having a 20-year-old male show her some level of affection made Gwen abandon her self-control. Within a short time, Gwen gave me the ultimate offer: “Do you want to come to my bedroom and fuck me, Patrick? I’d like that a lot. Will you?” She was almost pleading with me to say yes.
“How can I possibly refuse?” I said to her. “I’m a typical male.” I set my plate of goodies on a table. Gwen took me by the hand and led me to her room. This was by far the fastest time elapsed from when I started a date to the time any girl and I had ended up in the sack together.
Gwen slipped out of her dress quickly and stood before me in her pristine, white undergarments. She really had a great figure for someone who had just turned 18 the previous month! “Do you like what you see, Patrick?” she coyly asked me.
“My erection says yes!” I told her, which made her laugh. I showed her I was being truthful by disrobing down to my briefs. There was a noticeable tent because of my stiff phallus. “I’m going to take off my underwear before my penis pokes a big hole in it!”
“Let’s both get naked!” Gwen declared with great gusto. “What are we waiting for?”
By the time I dropped my underwear to the floor, Gwen had done the same with her bra and panties. We glanced at each other momentarily, smiled widely, and met in the center of her bed for some carnal fun. While Gwen positioned herself on top of me to continue her kissing spree, I grabbed her luscious breasts and began to fondle them.
“Well, I know what part of my body you like best!” Gwen said between kisses.
“You’ve got great tits, Gwen. That can’t be denied,” I told her as I began to amuse myself with them. None of the four girls I had bedded previous to Gwen had jugs like she did. They were magnificent. I figured Gwen could have a career as a bikini model—if she could be shown from the neck down.
Gwen never stopped kissing me as she placed her right hand on my erect penis and began to stroke it gently. The sensual feeling was amazing. For a girl who claimed to have never been kissed, she certainly knew how to treat a male bedmate!
“Gwen, you’re going to make me come way too soon!” I warned her. “I don’t want that to happen. I want to please you with my hard dick for a long time before I have an orgasm. You deserve it!”
“Please do, Patrick!” she responded. “Roll me onto my back and do your stuff!”
Gwen used her fingers to spread her pussy lips open. I felt obligated to lick her vagina, which she had not expected. She absolutely enjoyed the sensation of my tongue, especially when it contacted her clit. She became moist in a hurry!
By this time, my penis was ready to erupt, so I repositioned myself to give Gwen a strong fucking. From a kneeling position between her legs, I shoved my throbbing manhood inside her slightly hairy vagina. I began slowly with short, slow thrusts. I steadily increased my fucking rhythm until my rod was like a piston going in and out of her.
Gwen was having the time of her life. “That feels unbelievably good, Patrick. Keep doing that to me...forever!” she declared with a long sigh.
“I wish I could but...” was all I got out of my mouth before I sensed a sizable ejaculation was on its way. I pulled out with maybe two seconds to spare and shot a creamy, white load around the area of Gwen’s navel. I felt great and moaned with delight. Gwen was giddy with laughter. I tugged on my penis to get the final few drops of semen to fall on Gwen’s sexy tits. She interrupted me, though.
“Let me help you with that!” Gwen insisted—and placed my still rigid member into her mouth. A few excellent sucks drained it dry. It had easily been the greatest sexual experience in my life—and from the most unlikely source.
Gwen grabbed a box of tissues from her nightstand. We used them to clean ourselves up—temporarily, at least.
“We’ll go through several boxes of tissues before morning, Patrick, if I have my way with you.”
I was all in favor of that! At that moment I concluded that bedding Timothy Barton’s homely sister was a far better way to spend a night than watching a Marx Brothers film festival.
We just snuggled silently for several minutes before Gwen asked me with a naughty grin, “What do you like best, Patrick—my baking or my breasts?”
“Both are excellent!” I said. “But your baking provided pleasure for only a moment or two. Your tits can provide hours of fun. In fact, I want to finger and suck on your nipples right now!”
“Please do, Patrick. I want you to be happy. I am!”
This post-fuck foreplay (for the lack of a better term) began to cause my penis to rise again. Gwen noticed.
“If you pull your lips from my boob, Patrick, I’ll give you a blow job so you can be super hard again. I liked sucking on it before and I want to do it again, Okay?”
I was not going to object, so I willingly complied. I lied on the middle of the bed and let Gwen pleasure me. She began to use her tongue very effectively. She had a cute habit of sucking, licking and kissing my erection in that sequence. It shouldn’t have surprised me—but it did—when I came very easily in Gwen’s mouth with my second orgasm in about 20 minutes.
“I’m sorry about that, Gwen!” I apologized. “That was an accident. I didn’t mean to cum in your mouth. A lot of girls absolutely hate it when that happens.”
Gwen’s expression did not change. She simply smiled and let my semen drip from her mouth onto her fabulous breasts—and then onto me. “A lot of girls are stupid, then!” she replied. “I totally loved the experience!”
Not long afterward Timothy entered his sister’s bedroom. We had forgotten to shut the door and Timothy was curious as to what had happened to us. He got the full picture. Gwen and I, both covered in my second cum shot of the evening, were busily exploring each other’s nude bodies with sensual gropes.
I expected Timothy to be furious at me and his little sister. He was not. In fact, he was just the opposite. Timothy seemed delighted that Gwen was no longer depressed and was sexually active—and not just with anybody. She had been fucking his best friend!
“Well, this absolutely worked out even better than I had hoped,” Timothy said with a beaming smile on his face.
“Sorry, it just sort of happened, Timothy,” I tried to explain.
“Hey, I’m glad it happened because I was determined it would happen,” said Gwen with satisfaction as she continued to fondle my testicles.
“Number please, Patrick!” demanded Timothy
“Huh?” I uttered in bewilderment. “What are you talking about?”
“I’m talking about our deal, of course. What’s your sister’s telephone number, Patrick? If I’m lucky, perhaps I can have the same outcome with your sister as you had with my sister!”