Her Daughter’s wingman

Holiday 2011

In this Issue:

• Their business trip romance became a journey to pleasure
• She gives him a booty call every week, and he comes running
• A daring dress leads to a sexy one-time tryst with a total stranger
• It was a late delivery and the messenger used the back door
• He was a hound, but one woman knew how to keep him in line
• Waitressing didn’t cut it, so she found a more lucrative profession
• With her husband away she turns to other consolations
• It took him nearly fifty years to get her, but it was worth the wait
• Her neighbor thought he was too big for her. It was a challenge
• Five young guys at his daughter’s wedding were hot for his wife
• Hidden Desires
• Biker Dude
• She hadn’t wanted to even go to the party, but it worked out great
• She earned her grade the hard way—making her professor hard
• This year’s annual sex pilgrimage was truly a trip to remember
• His taste for full-figured girls was tickled right in his own back yard
• With both their spouses away, it was too good an opportunity to miss
• He offers up his body for her to play with—she takes it from there
• This sultry summer idyll features a hot stranger and a steamy climax
• Giving head came naturally to her—and was she ever hooked!
• For some of the prom-goers it was hell night, for others pure magic
• That first encounter with her boyfriend’s manhood was a hit
• They had talked about swinging with another person, but they hadn’t figured on two . . . and then four . . .
• MIDNIGHT at the TUNNEL of LOVE
• They expected it to be a threesome, but the party grew some
• Here’s a smutty new take on “employee evaluations”
• Her old flame turned up suddenly, and it was better than old times
• Her Daughter’s wingman
• A PROMISCUOUS WIFE, A RANDY FRIEND AND AN UNRELIABLE DOG
• HIS WIFE LIKES TO PLAY WAITRESS IN JUST A SEE-THROUGH NIGHTIE
• THE STRANGER WANTED TO FUCK HER, AND HER HUSBAND HELPED
• ONCE HER TUBES WERE TIED SHE COULD REALLY LET HERSELF GO

When our daughter (I’ll call her Cheryl) came home from college for Christmas break, my husband and I meant to take her on a weekend ski trip. We’d pulled out all the stops, even booking a deluxe suite that had its own hot tub!

Well, leave it to my husband to break his leg just before we were supposed to go skiing! When it happened I suggested staying home with him, but he wouldn’t hear of it, saying that Cheryl and I should go and enjoy ourselves. I had to admit I didn’t mind going alone with my daughter. Though we were very close when she was younger, we had grown apart over the years, and I was hoping that the ski trip would be an ideal opportunity to spend some quality time with her.

Cheryl and I hit the slopes as soon as we arrived, and had a great time. On one of the more difficult hills she raced well ahead of me, and when I finally made it to the bottom I found her talking with a trio of young men about her age. They were laughing and having a good time, and I figured that would put an end to our togetherness.

To my surprise, however, Cheryl waved me over and introduced me to the guys—Lars, Randy, and Ira. She quickly involved me in the conversation, and while the age difference made things a little awkward at first, Cheryl can be very sociable, and in no time at all she had the guys treating me more like her sister than her mother.

After a while Cheryl pulled me aside and said she needed to speak frankly with me. I saw how serious she was, and said she could tell me whatever she wanted. She surprised me then by telling me she hadn’t had sex for a couple of weeks and while all the guys were cute, she had her sights set on Lars, who she was sure could take care of that itch.

Now I wasn’t really surprised that my very attractive daughter was sexually active, but I’d never dreamed she would be so open about it, especially with me. Still, she was 20, and could live her life however she chose. I said as much, and gave her my approval to do whatever she wanted.

Cheryl seemed relieved, then followed up by asking me to be her “wing­man.” When I said I had no idea what that meant, she explained that since she would be focusing her attention on Lars, the other two guys might get jealous and try to spoil things. My job would be to keep them entertained by being very friendly with them—even going so far as to flirt with them a bit.

I was shocked at the idea, and quickly reminded Cheryl that not only was I old enough to be their mother, but I was also a married woman. She said not to sell myself short; I was still very attractive, and Randy and Ira had definitely been checking me out. She assured me that if I gave them a little encouragement, they’d be all over me.

As to my second objection, she said that this was a girls-only trip and whatever happened would stay between the two of us. Besides, it wasn’t like a little flirting was going to hurt anyone. I might even enjoy it. She added that if I wanted to take it further than that, it was fine with her. As far as she was concerned, after 25 years of being with the same man (even if it was her father!), I was entitled to cut loose if I wanted.

Her proposal stunned me. I had ­always been a faithful wife and had never considered straying. But here was my own daughter, not just encouraging it but making it sound reasonable! I collected enough of my wits to say that I would serve as her wingman, but only for the sake of her sex life, not mine. She said that was fine, but the teasing way she said it indicated that she had her doubts.

Cheryl’s assessment of Randy and Ira was on the money. All it took was a few suggestive remarks and sultry glances, and the guys were practically tripping over one another trying to impress me. I was so flattered by the fact of these two hunks vying for my attention that I actually found myself thinking about Cheryl’s suggestion. Both of the boys were cute, and with their youthful exuberance they were a stark contrast to my staid husband.

After skiing for most of the day, the guys invited us out to dinner, so Cheryl and I returned to our suite to get ready. It was a good thing her father wasn’t around, as the outfit she chose was so skimpy, it would have given him a heart attack! When she saw the dress I had brought, she scoffed, saying that while it might be appropriate for playing bridge with the girls, there was no way she was letting me embarrass myself by wearing such a thing. When I said it was the only dress I brought, she said I’d have to borrow one of hers. I said there was no way I could wear an outfit as scanty as the one she had on, but she assured me she would find me one that was more conservative.

While the dress Cheryl gave me did have a bit more substance to it than the one she was wearing, because I’m a bit taller and bustier than my daughter I ended up showing off at least as much flesh as she did. She thought it looked wonderful, and said she was jealous of how good I looked in it. I told her to stop teasing, but she assured me she was serious, and to prove it she challenged me to wear it to dinner and see the guys’ reaction. Somewhat reluctantly, I agreed.

Sure enough, when we met the guys they looked us over with equally hungry stares. Again, the fact that they seemed to regard me as being as attractive as my daughter stroked my ego in a way I hadn’t experienced in years. Despite the oddness of the situation, I quickly found myself having a good time.

When dinner was over, the five of us went to the hotel lounge for drinks. The guys saw to it that our glasses were always filled, and it wasn’t long before I was feeling no pain. After several drinks, Cheryl took me aside and told me that she and Lars were going to be using our suite for an hour or so, and that she would call me to let me know when it was okay to return.

That was fine with me, as I was genuinely enjoying the guys’ company, so I told her to have fun. She gave me a wink and said she certainly planned to. Then she and Lars took their leave.

They had been gone for only a few minutes when Randy suggested that the three of us go back to their hotel room and continue the party there. This put me in kind of a bind, since it would be awhile before I could return to our suite. But I didn’t feel like staying in the lounge alone, so I accepted the invitation, thinking that I would just stay until Cheryl called, and then leave.

We had barely entered the room when Randy grabbed me and gave me a deep kiss, one far more passionate than anything my husband had given me in years. It actually left me weak in the knees! When he broke off, I ­staggered a little but was immediately caught up in Ira’s embrace. He gave me a kiss as well, with his tongue darting into my mouth. Any thoughts of ­resistance swiftly faded away as I melted in his arms.

I felt someone unzipping my dress at the back, then easing it off my shoulders until it slid down my body and pooled at my feet. My bra, panties and hose followed quickly, leaving me naked.

Ira guided me to the bed, then laid me out on my back and went for my breasts. My nipples are very sensitive, and the way he alternated between sucking and tweaking them had me writhing around with my head thrown back. Randy focused on my pussy, eating me out with a tongue that felt so long and so deft, I could have sworn it was prehensile.

I could barely believe what was happening to me. Before marrying my husband I had been with exactly two men, and now I was with two men at the same time—and it felt incredible.

Ira worked on my breasts so well that I didn’t immediately miss Randy’s tongue when it left my pussy. But when I felt a pair of hands spread my legs, I raised my head just in time to catch a glimpse of his quite sizable cock just before he shoved it up to the hilt inside me. The sudden sensation of that stiff young pole filling my pussy caused me to come without warning! I couldn’t remem­ber the last time I had climaxed so quickly or so powerfully.

Ira kept sucking on my breasts while Randy began pounding away. He lasted a lot longer than my husband generally did, and I came a second time before that stud blew his load. I have always loved the feeling of a guy’s cock twitching inside me, and that turned me on even further.

When Randy removed himself from my pussy, Ira was quick to take his place, picking up where his buddy had left off. Now I was so into it that I began lifting my hips to meet each of his thrusts, and this time I came so hard, I cried out loud, which triggered Ira’s orgasm, and I was filled with another load of virile seed.

Ira pulled out of me and moved up on the bed so he was sitting with the headboard behind his back. He pointed at his cock and asked if I would mind cleaning him off. Now my husband was the only man I’d ever blown, and I wondered what a different cock might taste like, so I got on my hands and knees and eagerly took his cock in my mouth. I unleashed my oral talents upon him, and soon he was fully hard again. Though he was a little bigger than my husband, I had no problem deep-throating him.

As I continued to suck Ira, I felt Randy’s hands on my hips, then felt him shoving his revived cock in my pussy again. As he began banging away, Ira tangled his fingers in my hair and began face-fucking me. I can’t describe how wonderful it felt having two cocks pumping in me at the same time, but I can say that I came more times that night in the span of a half-hour than in any full night of my entire life.

Ira came in my mouth, and I greedily sucked down his load. I’d just finished up when Randy said he was about to blow. I begged him to fill me up good, and he most surely did.

After that the guys played with my body until they got hard yet again. Then they repositioned me on the bed so my head was hanging over the side. This time Randy went for my mouth while Ira got between my legs. They were a lot more patient this time, as well as more coordinated, and they fucked me for what felt like forever. Eventually they came together, and my own orgasm was so powerful, it actually caused me to pass out! That was a first for me.

I woke up the next morning sandwiched between those two young hunks. A part of me knew I should feel guilty, but the truth was, I had loved every second of it! I found myself agreeing with Cheryl that after so many years of faithfulness I was entitled to a little fun.

I was covered in sweat and dried semen, and really needed to clean up. Trying not to wake the guys, I got up slowly, snuck in the bathroom and started up the shower. I was nearly finished when the curtain was drawn aside. Naturally I thought it would be either Ira or Randy, so I gasped when I saw Lars standing there! I reflexively covered my breasts while he looked me over.

“Damn,” he said, “I thought Cheryl had a great body, but yours is even better! Want some help with washing your back?”

I was already leaning toward accepting Lars’s offer when he took off his clothes and revealed a cock that was even larger than those of his friends. That sealed the deal! He slipped up behind me and ran his hands up and down my body, focusing especially on my breasts and getting me really aroused. After doing that for a while, he had me lean forward with my hands against the tile, my legs spread and my ass sticking out toward him. Then he grabbed my hips, sank that big cock in me and began fucking away.

It was my first time having sex in the shower. I definitely enjoyed it, and came before Lars did. He was so ­focused on pounding my pussy that he never did get around to washing my back, but I wasn’t about to complain about that.

After we finished up, I managed to get dressed and slip out of the room without waking the others. When I ­returned to our suite, I found Cheryl waiting for me. She said she would ask me how my night went but she could guess by the smile on my face. I asked her why she hadn’t called me the night before, as she said she would when the coast was clear. She grinned and said she thought she should leave me with the guys and let nature take its course.

She asked me to tell her everything that had happened. I refused at first, but then she started going into graphic detail about what she had done with Lars, and the next thing I knew I was spilling my guts, about everything—­except my shower session with Lars. She said it sounded like I’d had a really good time, and joked that we should switch partners so she could have two cocks too. I assured her that what had happened was a one-time event for me, not to be repeated. She laughed and said we should wait and see how things turned out today.

This time when we hit the slopes the guys joined us immediately, and we spent most of the day skiing. In mid-afternoon a group of four guys came over and started talking to Lars and the others. It turned out that they all went to the same college and knew each other. Just as the newcomers were about to leave, Cheryl suggested they hang out with us, saying, “The more the merrier, as my mother can attest to.”

Talk about being embarrassed! I tried laughing it off, but I knew I sounded nervous.

At one point I saw Ira talking with the new guys and pointing at me. Judging by the way they smiled, I could guess what the topic was. After that the newcomers were nearly as friendly with me as Randy and Ira were. I was also getting brushed up against a lot, far too many times to be accidental, though I pretended to be unaware of it.

When evening rolled around, Cheryl suggested going back to our suite to party. When we got there, she proposed that we all take a dip in the hot tub. Lars said it sounded like fun but none of the guys had brought swim trunks. She whispered something in his ear which made him smile and say that that would work. Then she dragged me in the bathroom so we could change into our bikinis. When I asked her what she had said to Lars, she just told me not to worry.

When we came out, the guys were already in the hot tub. Upon seeing our attire, they whistled and made highly flattering comments about both of us. Randy and Ira insisted that I sit between the two of them. The tub wasn’t really meant for nine people, so it was a tight fit—not that they seemed to mind. Cheryl sat directly across from me, practically right on top of Lars.

The sexual tension was already high, and it rose still more when my daughter began making out with Lars. I can’t say I was surprised when Randy and Ira began fondling my body under the water. I moved slightly, and my hand brushed over Ira’s lap, feeling something long, hard and naked, and I realized that he wasn’t wearing anything! I reached over to Randy and discovered that he was in the same state.

So that was Cheryl’s solution to the swimsuit problem! The knowledge that I was surrounded by seven naked young hunks sent my mind spinning. I was so distracted that I was unaware of Randy undoing my top—until I saw it floating away! Now everyone had a perfect view of my breasts down to the nipples, which were floating just above the water.

Cheryl declared that it was now ­officially a party and discarded her own top, to the delight of all the guys. She moved onto Lars’s lap and started squirming around. After a minute or so, she began to bounce up and down in the water. I couldn’t believe it. I was watching my daughter have sex with a man, and obviously enjoying it. I found myself getting incredibly turned on at the sight.

Obviously I wasn’t the only one. Randy said that that looked like fun, and the next thing I knew he had me by the hips, lifting me up high enough to put me over his lap. My hands were operating on automatic as I pulled my bikini bottom aside grabbed his cock and positioned it right at my opening. He lowered me over it, filling me inch by inch. Pretty soon I was moving up and down even faster than my daughter, with my large breasts splashing water ­everywhere as they bounced wildly. What totally amazed me was what a turn-on it was having sex that way in front of everyone, and I came twice in rapid succession.

Soon after that, Cheryl gave a cry of her own, then stopped bouncing as Lars grunted out his orgasm. While he was catching his breath, my daughter announced that she was going “around the clock,” and with that moved over to the guy next to Lars and sat down on him. Seconds later she was churning the water once again.

Now Randy picked up his tempo, and within seconds he filled me with a load of semen. His cock had barely stopped twitching when Ira pulled me over onto his lap and stuffed me full of cock. When he finished up, I moved of my own accord to the guy next to him. I couldn’t believe how great it felt being repeatedly filled with cock.

Since Cheryl was moving from man to man in the same direction that I was, we remained directly across from one another the whole time. At one point her eyes met mine, and we exchanged looks of pure delight. I had never imagined that quality time with my daughter would consist of us getting fucked in a hot tub full of gorgeous young studs, but I sure wasn’t complaining. If anything, sharing the experience made me feel closer to her than ever.

Eventually we completed the circuit and ended up with the guys we started with. At that point we got out of the tub and continued the party inside. Over the course of the next few hours, my daughter and I were fucked in every position and combination imaginable. At one point we did all the guys at the same time. We each had one in each of our holes and took turns jerking off the seventh stud.

When I woke up the next morning the guys were gone, which was probably for the best, since we had to leave early to make it back home. When Cheryl asked me how I felt after finally cutting loose, I admitted that I’d had the time of my life, and the only thing I was sorry about was that we hadn’t done it sooner.

That was a couple of months ago. Last week Cheryl called to say that spring break is coming up and to invite me to go to the beach with her. My husband is thrilled at the idea, figuring my presence will keep her out of trouble. I assured him that I do plan on staying close to her, and not letting her do anything I wouldn’t do. So everybody is happy.

—Name and address withheld