To All the Moms I've Loved Before

It was my 18th birthday in May of 1988 and I had arrived at my friend Jenny's house. I was picking her up and we were going to a party. I wish I could say Jenny was my girlfriend, but I ended up in the friend zone with her.

Over the course of my high school years I'd managed to have several close girl friends, not girlfriends, but friends that were girls. I can't explain how every girl I met ended up liking me as a friend but not wanting to ever go out on a date. I wasn't the best looking guy or the most popular, but I thought decent enough looking and had my share of friends in school. I was 6'1 and 175 pounds, on the wrestling team, and in pretty good shape. All that said girls my age just wanted to be friends and nothing more. On the flip side older women seemed to love me. Growing up my mom's friends, aunts, friends mom's always seemed to gravitate towards me. The older I got the more attention older women gave to me. They always went out of their way to make small talk with me and some flat out flirted with me. As much as I enjoyed the attention it didn't help my current situation of being 18, a virgin, and always surrounded by hot girls who wanted nothing to do with me in a romantic way.

I rang the bell and Jenny's mom answered the door. She gave me a big hug. "Happy birthday Paul." I enjoyed the embrace as she was pretty attractive. She could have passed for Jenny's older sister. She was 40, 5'5 with auburn hair, a small set of breasts, and a cute petite body. The hug lingered and I finally broke it off as I was getting embarrassed.

"Thanks Mrs. Steele. It's good to see you. Is Jenny ready?"

"No, she'll be a few more minutes. Come in and wait." She led me to the kitchen where her husband was sitting reading the paper. We exchanged greetings and he went back to his paper. Mrs. Steele sat next to me at the table. "Now Paul, I want to take you out to lunch sometime soon for your birthday." We went back and forth after I said that wasn't necessary and ended up agreeing on the following Friday as I was taking a day off school. Jenny eventually came to the kitchen and we set out.

That Friday I'd had a doctors appointment in the morning and my parents just let me have the whole day off from school as my grades were good and I'd already been accepted to college. At 11:30 Mrs. Steele pulled into the drive and I walked out to her car. We set off to the restaurant. After getting seated and ordering we began to chat. It was the usual banter. I felt comfortable around Mrs. Steele and was enjoying our time together.

I felt truly at ease and decided to spill my guts to her. "Mrs. Steele, do you think I'm attractive or is there something wrong with me? And I want your honest opinion because I really need to figure out how to get a girlfriend."

"Paul, you are very handsome. Any girl would be lucky to have you as a boyfriend. Don't worry you'll meet someone soon enough."

I explained to her how not only was I a virgin, but hadn't even kissed a girl before. I was scared to go to college not having any type of experience. She kept reassuring me and pointing out all my attributes. She made me feel better about my situation. Our lunch came out and the subject changed as we ate.

She drove me back home and asked to use my bathroom. We went inside and I showed her the way and waited in the front room. She finished and as she was about to leave she turned, "When are your parents getting home?"

"Not for another few hours. Why?" With that she grabbed my hand and led me to the front room couch. "What's going on?"

"No one is to know about this, okay. I mean it." I wasn't sure what she was talking about so I just nodded my head. She then touched my cheek and leaned in and began kissing me. Her tongue entered my mouth and I began to mimic her lead. I touched her cheek gently and kissed her back. My body felt electric and I instantly had an erection. I'm not sure how long our make out session lasted but it seemed to last forever and end too quickly at the same time. She pulled back smiling. "I think you'll be ready for any girl you meet in college. You're a natural, you did well."

"Yes ma'am," was all I could squeak out. My cock was straining in my pants and I had to adjust myself. Mrs. Steele followed my hand and saw my predicament.

"Oh my," was all she said as her eyes were staring at my hard on. Her hand tentatively reached down and caressed my bulge. I just moaned and watched her fingers rubbing the outline of my erection. I looked to her face and we locked eyes for a time, my eyes pleading for more but I was afraid to talk.

Then the most amazing thing happened as she slid to her knees facing my crotch. She unbuttoned my jeans and unzipped the fly. Her hands grabbed the side of my pants and I lifted my ass as she lowered my jeans and underwear. I looked down as she gripped the base of my cock and slowly began jerking. I was in seventh heaven or so I thought until her lips surrounded my head. She started bobbing and each time she reached my head she would twirl her tongue around it. I'm not going to lie, she maybe sucked for 45 seconds to a minute before I started cumming. I think she may have been startled, but her mouth never left my penis and she swallowed what had to have been the biggest load in my young life. She removed her mouth and looked at me, "You have to warn a girl when you are about to cum. Let her decide if she wants it in her mouth or elsewhere."

"Yes ma'am." She sat back next to me and I believe was about to leave when I asked, "Could I, um, do that to you. I promise I'll try my best and do whatever you tell me." I rattled off some other nonsense and trailed off not making any complete sentences.

She pointed to the floor and I quickly got to my knees in front of her. Mrs. Steele had worked in the morning and had on a skirt. I ran my hands up her nylon covered legs and lifted the skirt to reveal the most beautiful sight that I'll never forget. Stockings up to her thighs and silk French cut panties. The aroma is still fresh in my memory to this day also. She gave me her instructions and I preceded to perform for the first time. Kissing, massaging, licking up her legs before turning my attention to her inner thighs and finally pulling her panties to the side to the ultimate treasure. Her taste was salty and tangy and I couldn't get enough. She guided me, corrected me, encouraged me and finally I brought her to orgasm and was still licking when she squeezed my head in her thighs until I stopped.

I sat back and we both looked down at my penis as it was ready for action again. Mrs. Steele stood, removed her skirt and blouse and laid down on the couch. "We've come this far, might as well make a man out of you. Take those pants off and come here." I again heeded her instructions and lay on top of her kissing her lips passionately. She reached her hand down and guided my cock to her entrance, "You must pull out as soon as you think you're about to cum. Do you understand?" I nodded once again. "When you pull out hump my panties and the rest will take care of itself."

With that she let go of my penis and I entered her and it dawned on me that THIS was the most blissful feeling that one could ever have in life. I began to make love to a woman for the first time. I lasted a little longer than I did earlier, but not by much. I had my head buried in Mrs. Steele's neck breathing heavily as I was humping away. She hugged me gently and let me enjoy my first experience. A few minutes later I felt my balls swelling, pulled out and rubbed my cock along her panties like she said. I came, shooting my seed up her chest, stomach and panties. I collapsed on Mrs. Steele and tried to take in her scent and etch into memory everything that just occurred.

With a laugh in her voice she said, "Well, you'll have to work on that a bit." She tapped me on the shoulder and I got up. We silently got cleaned up and dressed. She kissed me fully and tenderly before she left.

That night I stayed home even though there was a big party. After dinner I watched some TV and went to bed early. Laying in bed I kept thinking about Mrs. Steele and if we would have sex again. My thoughts then drifted to other women that were especially nice to me. I wondered if this experience could give me the confidence or blueprint to have similar encounters. I'd soon find out.

I had a job as a dishwasher at an Italian restaurant that was only open evenings so after graduating I had mornings and the early afternoon off. A neighbor down the street asked my mom if I'd like to make some extra cash for college. She had a couple rooms she wanted painted and her husband didn't have time.

I took the job and walked down to Mrs. Weekly's house Monday morning. She let me in and showed me the rooms she wanted painted and had all the supplies ready to go. I figured it would take me a week to complete the work. I thanked her for the job got busy.

After a few hours Mrs. Weekly told me she had lunch ready. I cleaned up the work space, washed my hands, sat down at the table and devoured the sandwich she had made. She was sitting across from me and we chatted after I finished eating. Mrs. Weekly was in her 50s and had a bubbly personality. She was a bigger woman, but curvy and she had huge tits. The bra she wore had them pointing straight out and I couldn't help but stare at them as we talked. She busted me several times, blushed but never said anything. I had to leave and go to my job, so I said goodbye and told her I'd see her the next morning.

The next day went the same and after she made me lunch we sat talking again. She asked me about college and in that moment I decided to try my virgin sob story out on her. The conversation went about the same as with Mrs. Steele. Mrs. Weekly was very nice, encouraging, and she boosted my ego saying how good looking I was. It was time for me to leave, so I thanked her for the kind words although I kept a dejected attitude. The topic came up briefly Wednesday and I tried to act happier, but still a little downcast.

I finished the painting Thursday. Mrs. Weekly made me lunch. She brought up my problem and was adamant that everything would work out for me. I told her I hoped so with sad eyes, but wasn't counting on anything. Nothing happened and I figured it wasn't meant to be. It was time for me to go again, so I asked for my payment. Mrs. Weekly left to fetch her purse, but came back a few minutes later saying she didn't have the money. She said she would go to the bank this afternnon and asked if I'd come by in the morning. "Sure, see you then." She gave me a long hug before I left and I enjoyed the feeling of her ample bosom pressing into me.

Friday morning I walked down to Mrs. Weekly's. She answered the door wearing a robe and let me inside. She told me to follow her as her purse was in the other room. The other room ended up being her bedroom. I followed her in and she got the money out of her purse and paid me.

As I was thanking her, she undid her robe and let it fall to the carpet. Mrs. Weekly had on a black corset with matching panties and a garter belt holding up black stockings. I took her beauty in and felt my cock rising. She took my hands and began kissing me. I tried to pretend to be a novice and since I'd only done it once before I realized I didn't know anything. Mrs. Weekly led me to the bed and taught me there was more than one way to pleasure a woman.

We necked for awhile before she pushed me down to her pussy. I started using the skills I learned, but Mrs. Weekly grabbed my head and pushed it right to her pussy and instructed me to lick her clit and finger her pussy. She was humping my face and tongue and in no time had an orgasm. I thought I was done, but she kept me down there. I'm not sure how many times she got off, but my mouth, nose, and chin were drenched by the time she let me up for air.

As my reward she had me lay on my back and she swallowed my cock in one quick motion. She was deep throating me and then slowly brought my cock out of her mouth before swallowing me whole again. The intensity was too much and I remembered to warn her I was close. She released my cock and laid it flat on my stomach. She then kissed my cock just below the head and started running her tongue back and forth my frenulum until I unleashed my load. Wow, the feeling was the same, but different.

I recovered and she lay back and brought my head to her breasts. I pulled down the top of her corset to release them. They plopped out revealing two massive globes. I started kneading and kissing them, relishing the feeling. I took a nipple in my mouth and sucked and flicked my tongue on it learning what she liked as I went. I swapped between the two for a time until my erection rose once more. I kissed her mouth and pushed into Mrs. Weekly. I was amazed anew at how great this felt. I was content to finish missionary, but she stopped me and rolled me to my back and straddled me.

As she grinded away her tits were in my face and I took a nipple in my mouth. She rode me for a few minutes and then got on all fours. I got behind her and started having doggystyle sex for the first time. I was gripping her hips slamming into her as hard as I could. I looked over and noticed she had a full length mirror on the closet door. I appreciated the view of her giant orbs flapping back and forth as I rammed away. I went at it for some time before I pulled out and shot several streams up her back into her hair, the last couple on her black panties. We collapsed together on the bed and both feel asleep.

I awoke an hour later still on Mrs. Weekly's back. My cock hard and ready, so I slipped it into her and she met my thrusts. Her sizeable ass propped me up as I shoved in and out. My pushing was getting more frantic and she told me I could finish inside her. That put me over the edge and I let go for a third time. As I was leaving she kissed me and said she might have more handy man jobs that might need my attention.

Until recently the owner of the restaurant I worked was an older Italian guy and his younger American wife. They'd just finalized a divorce and now it belonged solely to Ms. Lewis. She had married the older guy for money I guess, but soon she was running the restaurant by herself. Word was he was out fooling around on her and gambling away their money.

Ms. Lewis was 31. She was hot with blond hair, a perfect pair of tits and an ass every woman would die for. She was also a bitch to everyone. Everyone except me. For whatever reason, she found a lowly teenage dishwasher charming. She'd always been a little sweet on me, but as her marriage issues ramped up she would spend more and more time in the kitchen, mostly flirting with me. I think she enjoyed seeing me turn red with embarrassment and fumbling what to say as she teased me. I was a different person now after my encounters with Mrs. Steele and Mrs. Weekly.

On most days I got to work before anyone besides Ms. Lewis to mop and set up the dining area. With her divorce finalized she was nastier than ever to the employees, but became more flirtatious with me. Everyday she would find a reason to touch me and make a remark innocently with a double innuendo. Today was no different. She walked up as I finished setting up the dining area and rubbed my arm telling me how good of a job I was doing. Before she could say anything else I took her hand and cheesily said, "I can do a lot of jobs good." She took her hand back, laughed at me and walked away towards the kitchen doors. I saw her look back at me as she went through.

The night was busy and steady, which made the time go by quickly. I was working methodically thinking about Ms. Lewis throughout the shift. I bet she hadn't had sex in some time between her divorce and work schedule. I was confident in my new found abilities.

The restaurant closed and I took my time cleaning up the last of the dishes. The chefs left and I let the closing waitress leave early as I volunteered to finish her front of the house duties. Ms. Lewis and I were the only ones left in the building. I completed the closing chores and walked to the office. Ms. Lewis was finishing up the books. The last person there would go to the bank with Ms. Lewis to make the night deposit.

She stood to leave the office but I stayed in the doorway. When I didn't move she looked up at me and was beginning to say something, but I made my move. I took her face in my hands and leaned down and began kissing her. I waited to be slapped, but instead she kissed me back. She was hungry for love and attention. We made out for 10 or 15 minutes in the doorway before I reached behind her and unzipped the full length skirt she was wearing. It dropped to the floor and I was rewarded with a pleasant view of her in red panties encased in sheer pantyhose. I lifted her up and set her on the edge of the office desk. I kissed my way down her neck, unbuttoned her blouse, and removed her bra. I massaged her magnificent breasts taking each in turn in my mouth. I kissed my way down her stomach, to her thighs, down her legs and sucked her pantyhosed covered toes. I made my way back up kissing her legs, thighs and licking her covered pussy, trying to push my tongue through the nylon. Her hands were gripping the sides of the desk and I stood kissing her mouth, reached between her legs and ripped her pantyhose exposing her panties. She gasped and l kneeled in front of her. I used all the skills I learned from my mature teachers and brought Ms. Lewis to a shaking orgasm.

As she recovered I stripped and sat in the office chair. I took her hand and without prompting she dropped before me and took my manhood in her mouth. She was more beautiful than ever with her lips surrounding my cock and sucked with enthusiasm, bobbing and licking. I let her go for a few minutes and stood up and bent her over the desk. I moved her panties to the side and slid in to the hilt and fucked her hard. We both came at the same time and lost in my passion I spent myself in her. She turned and I began to apologize, but she just kissed me. We left the restaurant holding hands, went to the bank and back to her place.

I had affairs with all three throughout the summer of 88 and beyond when the chance arose. Mrs. Steele, Mrs. Weekly, and Ms. Lewis taught me life lessons, how to be a man and a generous lover. I also provided something to them. Companionship, conversation and love they were not getting at home. I'm not proud or ashamed, I'm not saying it was wrong or right, I'm just saying that it happened and I wouldn't change a thing. I've been happily married 25 plus years because of the main lesson I learned from them, attention and devotion to my wife. I'm thankful for those lovely women and rarely a day goes by when I don't think of one or all three of my first lovers.